Most enablement teams measure the wrong things—and Jonas Master has the conviction to say so.
After three and a half years scaling Rippling's enablement function from 5 to 36 people while the sales org grew from 350 to 2,200+ reps, Jonas has strong opinions on what actually drives sales outcomes versus what just makes enablement teams feel productive.
In this episode, Jonas joins Alex to discuss building enablement infrastructure at one of the fastest-scaling companies in B2B SaaS—and why the conventional playbook doesn't work at Rippling's level of complexity.
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Alex Kracov: So you've been at Rippling for just over three years. Can you walk us through a little bit of like what that journey's been like? Like what did enablement look like when you joined and how has it sort of evolved to today?
Jonas: Yes, it has been a pretty wild ride for three and a half years. So just to start with some numbers, when I started the sales org was about 350 to 400 in total rolling up to our CRO. And we had an enablement team of about five that I inherited when I started here. And with the main goal of kind of modernizing the function, increasing functional maturity and building out an enablement team that would allow us to scale.
Fast forward three and a half years. The sales team is now about 2,200 and the enablement function is 36 people — or we will be by the end of the year. A good plug that we are actively hiring. So if you're out there in enablement, please do reach out. I'm talking to pretty much everyone out there in the marketplace. But yeah, rapid growth within the enablement function. We've had to build a ton of structure within that. I've had to make sure that we're allowing the overall revenue team to scale and Rippling kind of has a tendency to grow in all directions at the exact same time. There's been a healthy demand for enablement services, let's say, over the three and a half years. And obviously happy to chat through kind of a little bit more of how we thought about doing that.
Alex Kracov: Totally, and we'll get into all this today. I think when we last talked the other day, you mentioned your kind of hot take was like enablement is usually done very wrong. And I thought that might be a good place to start today's conversation. I'd be curious, like what's your philosophy behind enablement and how did you kind of instill that philosophy as you started at Rippling and have been leading enablement for the last couple of years?
Jonas: Yeah, I don't want to feel like I'm gonna get this reputation for being like a total iconoclast. But I do think learning from the field over the last couple years I've definitely had a good front row seat of things that have worked and things that haven't. And I've seen the overall enablement function evolve a bunch in my time here. So first thing that I think generally enablement teams do wrong — I'll go through a couple of quick hits. First is oftentimes enablement teams will optimize for the training rather than optimize for the outcome. My general two cents here is training's a bit overrated. Thinking that that's the final destination is kind of thinking about things in the wrong way. And really at the end of the day, the Enablement Function's job is to drive sales outcomes and increase seller proficiency, not to deliver trainings that get five stars and people love sitting in.
The second thing that might be a little bit different is that I've kind of — as a necessity being the mother of invention here — landed on a highly specialized enablement model, which now I have a ton of conviction is the right way to drive maximum impact back to the revenue organization rather than having like a super horizontal or kind of broad enablement remit in terms of the way we point sellers. So I can go a little bit more into that because there's probably a bit of a spiel there, but yeah, I've definitely learned that in the last three and a half years at Rippling as well.
Alex Kracov: Can you actually talk about that? I'd be really curious. When you talk about a highly specialized enablement model, is that how you structure your team of 36 people? Is that what you mean by that? Or is it the programs that everyone's doing?
Jonas: Yeah, like I've been doing it since 2014. I've seen pretty much every team structure and also the way that changes have been driven to sales orgs. And I've been a part of a lot of the top-down initiatives — you know, we are going out there and we're now a Sandler shop. So everyone gets trained on Sandler. We're now a Command of the Message shop. So everyone does that. You spend your million dollars. You have your kind of episodic training sessions. And I mean, this is no disparaging on those methodologies, but I find kind of the overall top-down peanut butter approach of just everyone gets the same thing oftentimes leads to lower adoption, lower pull-through, lower actual results.
And for me, the absolute inverse of that is letting the decision-making and letting a lot of the building happen as close to the edge as absolutely possible. So the way we've structured our team is that each sales segment that has basically over 50 sales reps has their own dedicated enablement business partner. They own like full stack end-to-end enablement programs. They partner directly with the VP of sales of whatever that segment is. And the intention is that they alongside sales leadership are really setting the agenda and making those decisions of what's going to be most impactful to move that particular business forward. And doing most of our enablement efforts — call it like the 85% — all happen right there, hyper localized with deep domain expertise within a very small universe. And personally, I've found that that has driven way more results, way more buying from sellers rather than pulling a thousand people into a really crowded Zoom and saying everyone's going to learn the absolute same thing.
Alex Kracov: And do you take it as far as it's like completely different sales process — like one team's on Sandler, one team's MEDDIC — or is it more like, hey, what are your needs in a specific region or product line? And then let's build the collateral or the trainings or the things that that team needs.
Jonas: Yeah, it's a good question. I mean there probably needs to be some background on Rippling because when I said necessity is the mother of invention, Rippling is the ultimate horizontal compound startup. We have 35 different SKUs, selling into many different lines of business. So our overall go-to-market motions are hyper varied. Everything from a micro segment with three-day sales cycles and like $3,000 ASPs up to enterprise, crossing that into a bunch of different product lines.
So by definition, we've had to adopt that specialized model because there is no peanut butter model that would really work. Now, when you look at new logo sales, our core teams — yeah, it hasn't gotten as crazy where my mid-market VP loves Challenger, so they're getting trained on Challenger and the SMB team loves Sandler, so they're getting that. It's a lot more, to be honest — the way I think of it is kind of the tactics informing the strategy. We take much more of a playbook approach rather than here's your sales methodology. We have a core number of steps in our sales cycle and then we do a lot of inspection on what are the elements that are working and who is doing those best.
And once you find those nuggets of what good looks like — you have Rep A that is absolutely smashing how they're opening up their calls, building rapport, and setting the overall agenda — it's like, cool, let's bake that back into the playbook, and now we'll get everyone trained and try to standardize on that. So it's an interesting thing where you're trying to reduce variation by getting people following the playbook, but you're always interested in the variation where you're like, ooh, who's actually doing something a little bit different that's actually working, so that we can then go back and codify that. We've taken that playbook approach and really roll that out in kind of a unitized method across all the different segments.
Alex Kracov: Yeah, totally. I mean, Rippling is such an impressive business. It's such an inspiration for me as like a horizontal product. It's crazy how many products you have across so many different verticals. And I'd be curious to kind of go a little bit deeper on — you mentioned in your answer a second ago — you kind of structured the team maybe on like the size of the company they're selling into, right? Super transactional sales versus more mid-market or enterprise. How do you think about the different product lines as well? You sell into completely different buyers — HR, IT, finance. Are you structuring the team and the sales around those personas or is it product line segment?
Jonas: Yeah, there's been an interesting evolution here. So when I was interviewing with Rippling three and a half years ago, most of the interview questions were centered around how do you deal with the cognitive load imposed upon an AE or an AM when you're at a company that releases seven new products a year and sells to completely different parts of the business? And how do you get them to grok all of these things that are just constantly getting added to the plate?
And there's a lot that we discussed there and a lot that we tried, but what we eventually figured out is we were seeing diminishing returns on the N plus one product launch where eventually the cup was completely full. Like we'd drop water in and it was overflowing. And that moved us in a pretty hard pivot to a much more specialized sales model where we have our core AEs and AMs. They still have a very large remit in terms of the products that they sell. But then we have a number of our adjacent product clouds that are owned by specialist AEs — we'll call them product AEs. And they work in an overlay model where the core AE will open up that opportunity, find the opportunity for a specialist product, bring in the specialist AE, co-sell the deal, and then the core AE kind of owns quarterbacking it beginning to end.
And when we moved to that model about three years ago, it was such a massive unlock. These product lines that were coming out of the gates and doing pretty well but kind of stalling a bit — just because our average seller just couldn't sell everything equally well — once we saw that specialized model within sales, which by the way is the theme for this podcast, Rippling specializes in how we do sales, how we do enablement, all those things. Completely unlocked that. Now some of our fastest growing product lines from zero dollars to hundreds of millions of dollars within a couple of years have been the result of spinning up those specialist AE teams that act kind of as those overlays to our core AEs and AMs.
Alex Kracov: Yeah, it's super interesting. And I imagine a lot of your business is land and expand, right? People probably start on the payroll side of things, and then you're like, okay, let's get you on the financial products. Can you talk a little bit about how do you train the sales team on the land and expand motion? Is it just the handoff from that core AE to now the product specialist? How do you think about that part of the sales motion?
Jonas: I mean, not that discovery is not important for every AE in the entire universe of sales, but I feel like it's even more important for us, especially when you're really understanding the full landscape of the tech stack that people are using and then figure out what they're open to consolidating within Rippling and what needs to just get integrated into Rippling. Oftentimes customers can only deal with so much change. So sometimes we'll get those customers who are like, look, this is an HCM and payroll evaluation. I know that there's a million other things we can do. Let's punt those for like six months down the line. Our sellers can't just be banging customers over the head saying like, no, you need to bring everything in house.
I think we've gotten really good at doing the right level of discovery to figure out where the breakage points and where the real pain points for customers exist by having 10 to 15 to 20 disconnected systems that don't really talk to each other. A lot of the things you were mentioning — running a business, there is this hidden tax on businesses just from running all these backend systems. And for small businesses, oftentimes that falls on the CEO, founder, COO, who just has to keep everything buttoned together. And that's where Rippling really shines, where we can get people bought in to the all-in-one platform there. And the more people start adding on, the more the light bulb starts going off of like, yes, this is actually automating away a lot of the work that I previously was doing.
Alex Kracov: Totally. I mean, that's been my experience with Rippling. I also feel like I'm paying Rippling a little bit more every year as I'm using new things.
Jonas: Hopefully we're massive ROI on that. But yeah, I didn't know we'd be getting into the Rippling sales pitch, but I love it. But it is interesting from an enablement standpoint, if you think about the level of information that you have to arm the sellers to possess — like, how do I really understand their current state and what the pains are going to be around that? How do I know to sprinkle the right amount of seeds of like, whatever you're doing for spend cards, ramp's awesome, like maybe you keep doing that with Ramp, but just so you know, if you integrate that into Rippling, then we can push it directly to payroll and there's no intermediary step between the two.
And there's a couple of those points in every deal where you can start sprinkling those seeds. And then that oftentimes opens things up for our AM land and expand motion, which is a hyper efficient motion for us. Like our AM team completely rocks. We make sure we have really happy customers. We make sure they understand how to use the product, but there are always opportunities to be discussing increased value because there's so much more that people can be utilizing.
Alex Kracov: And I guess one of the other challenging dynamics with operating such a horizontal product is you're operating in all these super competitive software categories. I think I saw there's like over 600 competitors on G2. So how do you think about the competitive enablement side of things? Like how do you teach reps about all these different categories and the nuances of selling Rippling versus competitor A versus competitor B?
Jonas: Yeah, it's a blessing and a curse. On the blessing side, we're competing against really impressive companies that have multi-billion dollar categories in themselves, which obviously gives us a lot of inspiration — there's tons of roadmap ahead of us to grow globally. PEO, global, spend — all of these areas are multi-billion dollar categories in their own right that we're growing really rapidly into. Awesome opportunity from a TAM perspective, huge headache from a competitive intelligence and arming sellers with the right information perspective.
So I would never say we are doing this perfectly, but I'm happy to chat through some of the things that we think have been helpful. First thing is, obviously, the more you specialize — the more that we have these PAEs — they know all the ins and outs of Ramp and Brex if they are the Spend AE. And we really rely on the specialist AE to do the best de-positioning, trap setting, et cetera. So that's kind of just built into the model.
Another thing that we've tried to help sellers do is just try to bucket competitors, where it's nearly impossible to say like, I need to know all the ins and outs of ADP versus UKG versus Workday and multiplied by a gazillion. But it's a lot easier to say like, all right, really there's like three buckets of competitors that you're going to come up against. There's your legacy payroll providers — they've been around for 30 plus years, they've largely grown through acquisition, here's like the common pain points that are going to happen. Anything that starts with "pay" or ADP falls into that bucket. Then there's like your modern HCM platforms who are awesome, like your Gustos, your Bamboos — customers will be on these, but here's our overall competitive playbook against them. And then here's how we do that against PEOs.
And the more I find we bucket, we allow sellers to do a bit of the pattern recognition of like, I don't know all the ins and outs of this specific provider, but I get structurally where the problems are going to be. And then we get them really good at de-positioning and trap setting.
Alex Kracov: Curious how you communicate all this to the AE teams. Do you have a bunch of battle cards that the enablement team or maybe your product marketing team is managing? Or is it more live training sessions?
Jonas: Yeah, yes, yes. I mean, if you looked into our Confluence, we have so many different pages on our competitors — battle cards, keeping them up to date, making sure that we have kind of the right information there. The fun thing about competitive intelligence in general is it's just constantly adapting. Where you were six months ago, you're going to have to completely change. If you're listening to enough Gong calls, you're going to start seeing like, you know what, this competitor who we had really good win rates against — they're attacking us in a new way. It's like, we need to come up with new objection handling now that we didn't have six months ago. So it is constantly evolving.
One, we've benefited from having a small but mighty competitive intelligence team that literally does nothing all day but think of all these things. They don't sit within my group in enablement, but they are as close of a dotted-line type partner as we could possibly have. We're working with them on the training, the content. They produce really helpful month-by-month insights on just our win rates against every competitor in the set, and then trend lines of like, is this trending up? Is it trending down? Are our programs actually delivering the results that we're hoping they're delivering?
And then the last thing I'd say is a lot of this is actually built into the core Rippling value props that we communicate with customers. If you look at our first call deck — which obviously I can't publish here — we get a lot of those verbal nods from customers because this is their life. They live with all of these different scenarios of working with the legacy HR and all the pain points surrounding that, or having the kind of discontinuous Frankenstack that they stitched together. The better we can articulate the pain of their current-day scenario and then show them how Rippling is fundamentally different, the better off we are in kind of kicking off that evaluation.
Alex Kracov: Makes a lot of sense. Alright, switching gears a little bit. Obviously onboarding is incredibly important. You've gone from 300 to 2,000 sales reps — you've been onboarding a lot of folks over the years. Can you walk us through what that journey looks like? If I'm a new AE starting at Rippling, what does my onboarding program kind of look like?
Jonas: Yes, I think onboarding is some of the most table stakes things that any enablement function has to nail. Like if you're an enablement team and you don't have ridiculously good control and insight into the strength and performance and health of your onboarding program, stop what you're doing right there and make sure that that is in a good spot — especially for fast growing companies like Rippling where we've been hiring, on average, like seven to 900 new folks per year in the revenue org.
So the first thing you would see in our onboarding is it's hyper specialized — surprise, surprise. I think we have 65 different tracks based on the sales role that you are in. Down to this level of specialization of like, you are a mid-market product AE selling our IT cloud products — that's going to be a slightly different path than an SMB IT AE selling IT products. And obviously completely different than the version of that for spend. And then completely different for the version of that person doing that in Dublin. So it gets into like 4D Rubik's cube territory pretty quickly. But again, this has been kind of the necessity as the business has grown, because going back to the idea of the peanut butter approach — you're not going to drive optimal outcomes and get people ramped up and hitting their numbers and building pipeline and closing by doing a totally generalist base layer of onboarding.
So depending on the role, it'll be between four and six weeks. The key thing that we've found in that specialized model that I think is super important for other enablement folks is figuring out the key milestones of the deal that that seller will have to execute once they're actually customer facing. Find the five core milestones and bake those into weekly certifications. Basically say like, look, in order to be a successful AE, you have to nail the first call discovery and demo that you're going to do. So our first certification is all going to be pointed at that. And then you need to figure out all of the training content that gets people ready for whatever that cert is. And if they're good at the cert and they pass that, you're like, cool, milestone done. I now feel good about putting this person on the phone and having them actually go and execute this crucial part of the sales process.
And that's largely the way our onboarding looks. It's kind of like chronological deal flow starting from initial discovery, ending with closing, and then a lot of inspection and certification that they can actually go out and articulate the things and do that in a real world setting. And once they get five checks, let's put them on the phones. By no means are we expecting them to be fully finished products, but we at least know we have an MVP — someone who is ready to be customer facing, at which point we can start transitioning to post-onboarding, manager coaching, things like that.
Alex Kracov: Makes its own sense. And then who is actually designing the curriculum for all of those different tracks? Do you have like one or two people who are just in charge of onboarding at Rippling or is it all of those specialized enablement people responsible for their own segment — like they're full stack enablement people who do the onboarding and post?
Jonas: Yeah, going back to first principles, it's like push decision-making down to the edge. So in terms of the content — like, what's the playbook, how do we get you really good at practicing, what's the right level of certification — that's decided on by that specialist PM and then obviously sales leadership. They're driving a lot of that input and content into the learning paths.
And then on top of that, we have a couple of people who actually administer all of the learning paths because we're hiring so much. If I had my specialized embedded PMs also doing onboarding and all the training, like that would eat up 70% of their time based on the amount that we're hiring, and they wouldn't be able to do that full stack. So they have heavy input on the decision-making along with sales leadership, but the actual administration is handled by a different team just to make sure that that team is freed up.
Alex Kracov: Makes sense. And is the training e-learning? Are you getting everybody into a room and talking about things? Is it role play?
Jonas: All of the above. But my general philosophy is that the best way to learn things is to, one, have it modeled for you — what good looks like — by someone who's really good at it. So oftentimes the person doing the training is an exemplar from the field. Who's our best mid-market rep? Who's our best mid-market manager who just got promoted? They're the ones demonstrating.
And then it's like, you need tons and tons of repetitions and at-bats to get good at those things, especially if you're new. So building in that time for practice, building in the time for role play, making sure people can go work with your managers. We generally say, if you can say it out loud four or five times, you're going to own it, you're going to make it your own. But the first time it comes out of your mouth, it's never good. So building in a lot of time for practice within onboarding is crucial, because you could have the best async content and e-learning in the world, but if people aren't actually doing the thing and taking those swings, they're not really going to get better at it.
Alex Kracov: And then how does the manager play into all of this? Like are they along the way with onboarding and working with their new team, or is it more like, go through onboarding and then you get passed off to your manager and your manager's there to reinforce all the things you learned?
Jonas: Yeah, I think the latter thing that you articulated is like a complete recipe for failure. I've dealt with — and there was to an extent this was kind of the modus operandi when I started at Rippling — managers like, yeah, cool, just hand me a fully formed new hire in eight weeks and they'll just start hitting numbers. You're like, no, man, this needs to be co-created and co-built. So I think the first thing that's important is those frontline managers need to have really strong input into the actual content that's being trained. And as I just said a second ago, oftentimes they're the best people to have in front of a room because they're the subject matter experts. They're the ones who actually have the respect of the team. And if you allow them into the building process, they're going to be a lot more bought in.
And then the second thing that I think is really important is there needs to be a concurrent manager learning path for every sales rep learning path. And I don't mean like when you're onboarding a new manager they get specific leadership training. I mean the manager needs to know week by week what they need to do to support their new hire's learning — make sure they're hitting the milestones. So they have their own checklist that we've helped co-create with them. And I just think the more skin that managers have in the game, the more they feel like it's their responsibility to properly onboard people — which by the way, they have ultimate skin in the game; if their team hits quota, whether they're good or not, that's on them. But really working them into the process is going to meaningfully drive results for your onboarding program.
Alex Kracov: Alright, so we've talked a lot about trainings, but at the beginning you sort of said, okay, trainings are just a step along the way. Enablement teams need to build more towards the actual outcomes of the revenue organization. So how do you think about that?
Jonas: Yeah, that's a good question. After all that talking about training — I mean, I do think from a new hire perspective you obviously lean a little bit more training heavy because you're starting with somewhat of a blank slate. But especially on the ongoing material, here's what I hate or what I think is a recipe for failure: an enablement setup where you're like, hey, we have a weekly enablement slot with the sales team, let's fill it with a training. And you're like, well, what should we train on next week? I don't know, let's do discovery. And the week after that, let's do multi-threading. And the week after that, let's do prospecting. And it's just these random shots in the dark.
And even if the content is fantastic, even if you are the Michael Jordan of sales trainers, you're going to have a muted impact by not having deeper focus on the outcomes that you're looking to drive. So when I say training's overrated, what I mean is all the focus on putting together these perfect trainings should get redirected to figuring out with sales leadership — what are the one to two outcomes that we are looking to drive amongst the sales team — and then putting a lot of the organizational muscle behind driving those over a longer period of time.
So it's like, all right, for March and April, let's just focus on multi-threading. We know that in deals where we get senior leaders involved, we have 75% higher win rates. Let's get everyone on board with that. It'll usually start with the training. But the thing that I find is most important is the pull-through, actual behavior change piece of that. Because all the training does is relay the information, which is usually forgotten a couple of days after. But all the activities after the training — whether it's let's listen to Gong calls, let's find out who's doing this really well, let's make sure there's visibility into dashboards, let's build a library of what good looks like, let's do some individual coaching and arm the managers to be a force multiplier — if you put a lot of the effort on that stuff rather than just the initial origination point, you're going to drive much better results. And also you can then point back at the actual changes that you're having as an org.
Alex Kracov: And I'm curious, how does that relate to your own success metrics as you think about the enablement function and you're talking to your boss and saying, hey, I'm doing a good job? Do you point to those same outcomes — hey, we increased close rates, enablement's doing its job?
Jonas: 100%. I mean, I think if this is one of these always-on motions, it becomes super easy at the end of the year when you're doing your annual self-review of like, what did we actually do this year? And you're like, well, we measure every program. And by the way, not all of them are going to be successful. Can you bat like .500, .600 on these programs? You're awesome. That's great.
I think my intuition is a lot of teams don't do it this way because they're somewhat afraid of being on the hook and having it proven that your enablement didn't work. And then they're like, ugh, I don't want to be in that scenario where we tried to do something, we measured it and it completely failed. And I think that natural preservation mechanism around that is like, let's not measure. Let's just — here's what we should measure — let's measure sentiment leaving the training. And that way, if we only measure that, we can say we delivered an awesome training. Is it our fault that it didn't lead to results? Like, who knows, there's a million things out there. But it's like, no — it's better to go out on a limb, try to have a little bit more skin in the game and really align with leadership on what's going to be important in terms of driving that for the team.
Alex Kracov: Not to get too enablement nerdy — what's the Kirkpatrick method?
Jonas: Not to get like too enablement nerdy on you, but there's the Kirkpatrick method for measuring enablement. There's four layers to it, and they go in order of value back to the business. So the least valuable — but the one that people do the most — is sentiment, which is like, did the employee like the training? The second one is knowledge: could they pass a knowledge test, or if you certified them, could they actually display that they know the things that you trained them on? The third — which is tough to do but really important — is behavior: are they actually translating that to customer-facing conversations, are they actually doing the thing live? And then the fourth is on the business results side.
The comfort zone, the safe zone for enablement is sticking in box one. Maybe box two, we certified people, they passed the certification. The elevated ones — the ones that actually deliver the most value — are can we track behavior change and then can we track business results? And one leads to the other. Like the idea is if we want to multi-thread more, we can see if there are more contacts associated with the account, and if so, is that leading to higher win rates?
On the behavior change front, an enablement team's best friend is Gong. I couldn't — it's the one tool where I'm like, if Gong got ripped away, I'm just retiring. Because it's the only way to measure behavior change at scale. You can really see day by day — is the training actually taking root and translating into a difference in behavior? And if we see that, that's kind of win number one on its own. And then it's like, well, let's see if our hypothesis was right that multi-threading more, which we are seeing happening, is leading to win rates. But oftentimes what I would direct an enablement person to is just focus on the behavior change. If you can actually prove that's happening, then the lagging indicator is you'll see if the hypothesis is true or not.
Alex Kracov: Super interesting. Alright, switching gears. Wouldn't be a podcast in 2026 without talking about AI. I'm curious how you use AI both for the enablement team itself at Rippling, but then potentially more interesting is the sales team at Rippling. What are they doing, and how are you enabling them to use all these different AI tools?
Jonas: Yeah, we have to talk about this. It has changed a bunch over the last six months, but I could say we've definitely taken a lot more of a role in orchestrating sales workflows with AI over the last six to 12 months, in partnership with our fantastic RevOps team. It would be completely unfair for me to try to hoard a lot of the credit for what we're delivering without mentioning them because they're doing a lot of the building.
It's kind of gone in a couple of phases for us. So phase one was like, we have all these tools, all these tools have their own native AI features. Let's use those and actually make sure we're getting the use out of Outreach's AI or Gong's AI or whatever else. But a lot of those are siloed just to that specific tool. In my mind, the next layer and the thing that I think would be most important that we've been focusing on is how do we figure out the orchestration that oftentimes lives in between the tech stack to make sales reps' lives way easier.
One thing we did here — even though it was kind of painstaking, I think it was really important — is we did a time and motion study.
Alex Kracov: What's that?
Jonas: You literally have your enablement team observe a day in the life of a seller, like a full eight-hour day, and do that over and over again. It was super old school. How much time did you spend preparing for your disco call? That was 15 minutes. How much time did you spend inputting info back into the CRM based on the call? That was another 15 minutes. How long did it take you to do CPQ and a quote? That's like an hour. And you could basically roll that up to figure out where the slices in time go and how much time doesn't go to actual selling activities.
And then once you put it on a slide like that and put it in front of sales leaders, oftentimes it's like a total holy crap moment. They're like, how many meetings? That's like — and just quantifying it is so powerful. Because once we did that, we just came up with a full stack rank of all the waste in the system — of which there is a lot — and this isn't impugning our sales team, this is like the processes that we've set them up to go and do. But once we did that, we were able to go work with our RevOps team and they're like, all right, how do we take pre-call research from 15 minutes down to 30 seconds with AI? And how do we take the post-call CRM updating down to zero seconds? Because we can just pipe Gong right into Salesforce and automatically update those.
Or it's like for us in Rippling, with such a complex deal cycle — BDR passes to AE, AE brings in SC, SC brings in PAE — there are so many of these handshakes, oftentimes which require like, let's meet for five minutes, let me write up a 10-minute Slack to tell you what's going on in the deal. It's like all of that's now automated. The second you're bringing in a PAE for spend, a deal brief goes to them with everything they need based on the Gong transcripts. So there's just so many of these breakage points that drain the life and time and energy out of your ranking fire seller. And we're just taking our way down the list with RevOps at this point.
Alex Kracov: Yeah, I mean, that's a great exercise everyone should do. It's worth it. That's the only way you figure it out.
Jonas: 100%. It's helpful to figure out the time and it's also helpful just to rally and cry. Because once you roll it up, it's just a number that you're like, we need to bring this number down.
Alex Kracov: Yeah. And the other interesting dynamic is Rippling itself as an AI platform. I know you just released Rippling AI last week and that was an awesome launch. How do you think about enabling reps to actually sell AI capabilities? Because I think one of the interesting dynamics with these products is they're like iceberg products — everyone has a chatbot, and it all sort of feels the same at the beginning, but there's a lot of different complexity underneath.
Jonas: There's a lot there. I think to your point, if you're a company and you're not talking about AI, your product marketing team should all be fired. So there's this wall of noise out there about that. And the main thing we've been focused on since this launch is obviously equipping our sellers to go out there and sell it. But the differentiation piece has been crucial here. Because if customers at the end of the day go and say like, cool, Rippling has an AI chatbot and that's just like Salesforce's AI chatbot or whoever, then we have deeply failed from an enablement perspective.
Because it's our opinion that our product is highly differentiated. And the reason for that — not to get back into the product pitch — but going back to the very beginning: AI runs on data. Your AI is only going to be as good as your underlying data sources. And if all your underlying data sources are siloed in 12 different point solutions, you're not going to be able to do any of the interesting cross-product AI queries and workflows that would really be impactful. And that's really the unlock with Rippling — all of the data lives in one place, it's all appended to the employee record, and because it all lives in Rippling, you can of course answer basic questions, but then you can also do really cool workflows, build really cool reporting, answer questions about your business that you would never be able to do with more point-solution-oriented AI.
But the real question is, can we get our sellers to explain that to customers? And can we get customers to believe it and see it and make it happen? So I don't know, we're a week into that — I'll tell you how we did in a month or so. We're super excited about the launch.
Alex Kracov: Yeah, I think it's a super interesting dynamic that we're all trying to figure out. I heard one of the founders of Intercom talk about how they give their customers a list of questions to ask their chatbot and competitor chatbots — and there's a lot of gotcha questions in there that they can only answer with their data model. That's a good idea.
Jonas: That's a good trap.
Alex Kracov: All right, I'd love to talk a little bit about your personal journey. You run a giant enablement team in a really big organization. How did you make that leap from kind of an enablement practitioner to a senior leader of other enablement people?
Jonas: Yeah, it has been a ton of fun learning and growing within the overall functional maturity of enablement. Where enablement 10 years ago, people were still arguing whether it belonged in product marketing or belonged in sales. It has been a rapidly developing function and it's been really fun to see how that's developed over the 10 to 15 years that I've been part of it. But fundamentally on my personal journey, it all started within sales. It was pretty much my first job out of college. I think it's the best job in the entire world if you are graduating from college and you're not an engineer or mathematician — get into sales. Learn just executing at a business level.
And I did that for a number of years and kind of moved my way up through the ranks and was managing teams. I was later managing really large teams — probably earlier than I would have anticipated, running a 150-person sales floor — and really had to learn how to get people with no sales background functional at sales and hitting numbers in a short period of time. And that's kind of where the light went off in my head: I kind of like doing this part of the job the best. Like being a sales leader, but I really liked seeing people improve — seeing that person who was struggling to hit their number reach quota for the first time, start walking around their office with that renewed confidence. It was just so cool to be able to do that and get people so much better at their job. So I was like, oh, this is actually a function. People get paid to do this. And I've kind of been on that journey ever since.
Alex Kracov: And what do you think has made you successful? What advice would you give to somebody who's earlier in their career and wants to be a big-time enablement leader?
Jonas: Yeah, going back to specializing — this might be self-serving since this is my background, so take it with a grain of salt — but I do think if you actually want to get into a career in sales enablement, you should start off your career in sales. Do the job that you are hoping to make better. I don't think it's impossible to be a successful enablement person if you've never sold. I just think it's way, way harder. Because developing that seller empathy, really understanding what it's like day in the life as a BDR, as an AE, as an AM, as a manager — that's probably the best experience you can have. Really understanding what the day-to-day is of a frontline sales manager, which is in my estimation the hardest job in all of business. Learn that, understand it. And once you can develop that deep understanding and empathy for it, I think it just gives you the pattern recognition to really understand what's going to be impactful and what won't.
And the more you can do that, the better you're going to be able to relate to sellers, to sales leaders. And oftentimes that's going to be the thing that unlocks you in your career — how do we grow the enablement function, how do we add more headcount to it? There's only one answer: be successful at sales, but also prove value back to the people who are making those headcount decisions, which is largely the VP of sales, CRO, whatever it is. And if they're the ones saying yes, we need more versions of that person because they are so additive, you're going to grow your function. So it's really about making sure that you can go and prove that value back to the business.
Alex Kracov: I'd love to end today's conversation with a question I'm personally very curious about. What's it like working in a Parker Conrad organization? I'm a big fan of him as a CEO, but he's also a very intense CEO in a good way. How does that impact you, the go-to-market team, enablement?
Jonas: Yeah. One day somebody has to write a book about the Rippling culture because it is unique and special and it stems from Parker. Obviously culture is like a diffusion from your most senior leaders and of course your founder CEO. So a couple of things that are unique about Rippling culture that I think have led to our success and are things that I absolutely love about working here.
First things first is just the pace of execution. Every software company in the world says it's fast. And then people start at Rippling and they're like, whoa, the treadmill is at 25 miles an hour and everybody is sucking wind. And I think there's almost like an intentional — our COO, Matt McKinnis, has talked about this — the engine should always be right below the red line. You don't want to completely overheat it, but in a very purposeful fashion, a big job of leadership is driving that pace of execution, especially as you're scaling. Because there's such danger of going from a thousand employees to 5,000 employees and then just everything becomes bureaucratic and slow. And thankfully that has not been the case at Rippling over the three to four years that I've been there.
So the pace is one. The second is there's a huge burden on leaders to be deep, deep experts and to actually do the thing. One of the fundamental principles that Parker has instilled in the org is this idea of "go and see" — which is, if there's a problem, if something's wrong with the business, the leaders need to completely take that to ground and go in the boiler room and turn on the flashlight and find all the cockroaches and do the actual thing to understand what that problem is. And that could end up being listening to a thousand support tickets or listening to a hundred Gong calls. Do the dirty, horrible work to figure out what is wrong, and then you can go fix it. And that's just been completely distilled into the overall operating rhythm of every employee in the business.
There are a lot more Ripplingisms, but those are a couple that I think make it super unique and fun to work here.
Alex Kracov: I love it. And I love the idea of just diving deep. You can only make change if you actually understand the actual problem. Thank you so much for the time today, Jonas. This was a lot of fun talking to you.
Jonas: I appreciate it. Thanks for the invite. It's been fun.
Jonas Master is VP of Sales Enablement at Rippling, where he leads a 36-person team supporting over 2,200 sales reps. Since joining three and a half years ago, he's scaled the enablement function ninefold while the sales org grew sixfold.
Before Rippling, he spent 5+ years at LogMeIn, growing from Sr. Manager to Director of Global Sales Enablement, overseeing a team of 18.
He was also previously Head of Sales at Goji, scaling the team from 50 to 150 reps and growing revenue from $t,3M to $22M in under three years.
Most enablement teams measure the wrong things—and Jonas Master has the conviction to say so.
After three and a half years scaling Rippling's enablement function from 5 to 36 people while the sales org grew from 350 to 2,200+ reps, Jonas has strong opinions on what actually drives sales outcomes versus what just makes enablement teams feel productive.
In this episode, Jonas joins Alex to discuss building enablement infrastructure at one of the fastest-scaling companies in B2B SaaS—and why the conventional playbook doesn't work at Rippling's level of complexity.
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Tools mentioned:
Methodologies & Frameworks
Alex Kracov: So you've been at Rippling for just over three years. Can you walk us through a little bit of like what that journey's been like? Like what did enablement look like when you joined and how has it sort of evolved to today?
Jonas: Yes, it has been a pretty wild ride for three and a half years. So just to start with some numbers, when I started the sales org was about 350 to 400 in total rolling up to our CRO. And we had an enablement team of about five that I inherited when I started here. And with the main goal of kind of modernizing the function, increasing functional maturity and building out an enablement team that would allow us to scale.
Fast forward three and a half years. The sales team is now about 2,200 and the enablement function is 36 people — or we will be by the end of the year. A good plug that we are actively hiring. So if you're out there in enablement, please do reach out. I'm talking to pretty much everyone out there in the marketplace. But yeah, rapid growth within the enablement function. We've had to build a ton of structure within that. I've had to make sure that we're allowing the overall revenue team to scale and Rippling kind of has a tendency to grow in all directions at the exact same time. There's been a healthy demand for enablement services, let's say, over the three and a half years. And obviously happy to chat through kind of a little bit more of how we thought about doing that.
Alex Kracov: Totally, and we'll get into all this today. I think when we last talked the other day, you mentioned your kind of hot take was like enablement is usually done very wrong. And I thought that might be a good place to start today's conversation. I'd be curious, like what's your philosophy behind enablement and how did you kind of instill that philosophy as you started at Rippling and have been leading enablement for the last couple of years?
Jonas: Yeah, I don't want to feel like I'm gonna get this reputation for being like a total iconoclast. But I do think learning from the field over the last couple years I've definitely had a good front row seat of things that have worked and things that haven't. And I've seen the overall enablement function evolve a bunch in my time here. So first thing that I think generally enablement teams do wrong — I'll go through a couple of quick hits. First is oftentimes enablement teams will optimize for the training rather than optimize for the outcome. My general two cents here is training's a bit overrated. Thinking that that's the final destination is kind of thinking about things in the wrong way. And really at the end of the day, the Enablement Function's job is to drive sales outcomes and increase seller proficiency, not to deliver trainings that get five stars and people love sitting in.
The second thing that might be a little bit different is that I've kind of — as a necessity being the mother of invention here — landed on a highly specialized enablement model, which now I have a ton of conviction is the right way to drive maximum impact back to the revenue organization rather than having like a super horizontal or kind of broad enablement remit in terms of the way we point sellers. So I can go a little bit more into that because there's probably a bit of a spiel there, but yeah, I've definitely learned that in the last three and a half years at Rippling as well.
Alex Kracov: Can you actually talk about that? I'd be really curious. When you talk about a highly specialized enablement model, is that how you structure your team of 36 people? Is that what you mean by that? Or is it the programs that everyone's doing?
Jonas: Yeah, like I've been doing it since 2014. I've seen pretty much every team structure and also the way that changes have been driven to sales orgs. And I've been a part of a lot of the top-down initiatives — you know, we are going out there and we're now a Sandler shop. So everyone gets trained on Sandler. We're now a Command of the Message shop. So everyone does that. You spend your million dollars. You have your kind of episodic training sessions. And I mean, this is no disparaging on those methodologies, but I find kind of the overall top-down peanut butter approach of just everyone gets the same thing oftentimes leads to lower adoption, lower pull-through, lower actual results.
And for me, the absolute inverse of that is letting the decision-making and letting a lot of the building happen as close to the edge as absolutely possible. So the way we've structured our team is that each sales segment that has basically over 50 sales reps has their own dedicated enablement business partner. They own like full stack end-to-end enablement programs. They partner directly with the VP of sales of whatever that segment is. And the intention is that they alongside sales leadership are really setting the agenda and making those decisions of what's going to be most impactful to move that particular business forward. And doing most of our enablement efforts — call it like the 85% — all happen right there, hyper localized with deep domain expertise within a very small universe. And personally, I've found that that has driven way more results, way more buying from sellers rather than pulling a thousand people into a really crowded Zoom and saying everyone's going to learn the absolute same thing.
Alex Kracov: And do you take it as far as it's like completely different sales process — like one team's on Sandler, one team's MEDDIC — or is it more like, hey, what are your needs in a specific region or product line? And then let's build the collateral or the trainings or the things that that team needs.
Jonas: Yeah, it's a good question. I mean there probably needs to be some background on Rippling because when I said necessity is the mother of invention, Rippling is the ultimate horizontal compound startup. We have 35 different SKUs, selling into many different lines of business. So our overall go-to-market motions are hyper varied. Everything from a micro segment with three-day sales cycles and like $3,000 ASPs up to enterprise, crossing that into a bunch of different product lines.
So by definition, we've had to adopt that specialized model because there is no peanut butter model that would really work. Now, when you look at new logo sales, our core teams — yeah, it hasn't gotten as crazy where my mid-market VP loves Challenger, so they're getting trained on Challenger and the SMB team loves Sandler, so they're getting that. It's a lot more, to be honest — the way I think of it is kind of the tactics informing the strategy. We take much more of a playbook approach rather than here's your sales methodology. We have a core number of steps in our sales cycle and then we do a lot of inspection on what are the elements that are working and who is doing those best.
And once you find those nuggets of what good looks like — you have Rep A that is absolutely smashing how they're opening up their calls, building rapport, and setting the overall agenda — it's like, cool, let's bake that back into the playbook, and now we'll get everyone trained and try to standardize on that. So it's an interesting thing where you're trying to reduce variation by getting people following the playbook, but you're always interested in the variation where you're like, ooh, who's actually doing something a little bit different that's actually working, so that we can then go back and codify that. We've taken that playbook approach and really roll that out in kind of a unitized method across all the different segments.
Alex Kracov: Yeah, totally. I mean, Rippling is such an impressive business. It's such an inspiration for me as like a horizontal product. It's crazy how many products you have across so many different verticals. And I'd be curious to kind of go a little bit deeper on — you mentioned in your answer a second ago — you kind of structured the team maybe on like the size of the company they're selling into, right? Super transactional sales versus more mid-market or enterprise. How do you think about the different product lines as well? You sell into completely different buyers — HR, IT, finance. Are you structuring the team and the sales around those personas or is it product line segment?
Jonas: Yeah, there's been an interesting evolution here. So when I was interviewing with Rippling three and a half years ago, most of the interview questions were centered around how do you deal with the cognitive load imposed upon an AE or an AM when you're at a company that releases seven new products a year and sells to completely different parts of the business? And how do you get them to grok all of these things that are just constantly getting added to the plate?
And there's a lot that we discussed there and a lot that we tried, but what we eventually figured out is we were seeing diminishing returns on the N plus one product launch where eventually the cup was completely full. Like we'd drop water in and it was overflowing. And that moved us in a pretty hard pivot to a much more specialized sales model where we have our core AEs and AMs. They still have a very large remit in terms of the products that they sell. But then we have a number of our adjacent product clouds that are owned by specialist AEs — we'll call them product AEs. And they work in an overlay model where the core AE will open up that opportunity, find the opportunity for a specialist product, bring in the specialist AE, co-sell the deal, and then the core AE kind of owns quarterbacking it beginning to end.
And when we moved to that model about three years ago, it was such a massive unlock. These product lines that were coming out of the gates and doing pretty well but kind of stalling a bit — just because our average seller just couldn't sell everything equally well — once we saw that specialized model within sales, which by the way is the theme for this podcast, Rippling specializes in how we do sales, how we do enablement, all those things. Completely unlocked that. Now some of our fastest growing product lines from zero dollars to hundreds of millions of dollars within a couple of years have been the result of spinning up those specialist AE teams that act kind of as those overlays to our core AEs and AMs.
Alex Kracov: Yeah, it's super interesting. And I imagine a lot of your business is land and expand, right? People probably start on the payroll side of things, and then you're like, okay, let's get you on the financial products. Can you talk a little bit about how do you train the sales team on the land and expand motion? Is it just the handoff from that core AE to now the product specialist? How do you think about that part of the sales motion?
Jonas: I mean, not that discovery is not important for every AE in the entire universe of sales, but I feel like it's even more important for us, especially when you're really understanding the full landscape of the tech stack that people are using and then figure out what they're open to consolidating within Rippling and what needs to just get integrated into Rippling. Oftentimes customers can only deal with so much change. So sometimes we'll get those customers who are like, look, this is an HCM and payroll evaluation. I know that there's a million other things we can do. Let's punt those for like six months down the line. Our sellers can't just be banging customers over the head saying like, no, you need to bring everything in house.
I think we've gotten really good at doing the right level of discovery to figure out where the breakage points and where the real pain points for customers exist by having 10 to 15 to 20 disconnected systems that don't really talk to each other. A lot of the things you were mentioning — running a business, there is this hidden tax on businesses just from running all these backend systems. And for small businesses, oftentimes that falls on the CEO, founder, COO, who just has to keep everything buttoned together. And that's where Rippling really shines, where we can get people bought in to the all-in-one platform there. And the more people start adding on, the more the light bulb starts going off of like, yes, this is actually automating away a lot of the work that I previously was doing.
Alex Kracov: Totally. I mean, that's been my experience with Rippling. I also feel like I'm paying Rippling a little bit more every year as I'm using new things.
Jonas: Hopefully we're massive ROI on that. But yeah, I didn't know we'd be getting into the Rippling sales pitch, but I love it. But it is interesting from an enablement standpoint, if you think about the level of information that you have to arm the sellers to possess — like, how do I really understand their current state and what the pains are going to be around that? How do I know to sprinkle the right amount of seeds of like, whatever you're doing for spend cards, ramp's awesome, like maybe you keep doing that with Ramp, but just so you know, if you integrate that into Rippling, then we can push it directly to payroll and there's no intermediary step between the two.
And there's a couple of those points in every deal where you can start sprinkling those seeds. And then that oftentimes opens things up for our AM land and expand motion, which is a hyper efficient motion for us. Like our AM team completely rocks. We make sure we have really happy customers. We make sure they understand how to use the product, but there are always opportunities to be discussing increased value because there's so much more that people can be utilizing.
Alex Kracov: And I guess one of the other challenging dynamics with operating such a horizontal product is you're operating in all these super competitive software categories. I think I saw there's like over 600 competitors on G2. So how do you think about the competitive enablement side of things? Like how do you teach reps about all these different categories and the nuances of selling Rippling versus competitor A versus competitor B?
Jonas: Yeah, it's a blessing and a curse. On the blessing side, we're competing against really impressive companies that have multi-billion dollar categories in themselves, which obviously gives us a lot of inspiration — there's tons of roadmap ahead of us to grow globally. PEO, global, spend — all of these areas are multi-billion dollar categories in their own right that we're growing really rapidly into. Awesome opportunity from a TAM perspective, huge headache from a competitive intelligence and arming sellers with the right information perspective.
So I would never say we are doing this perfectly, but I'm happy to chat through some of the things that we think have been helpful. First thing is, obviously, the more you specialize — the more that we have these PAEs — they know all the ins and outs of Ramp and Brex if they are the Spend AE. And we really rely on the specialist AE to do the best de-positioning, trap setting, et cetera. So that's kind of just built into the model.
Another thing that we've tried to help sellers do is just try to bucket competitors, where it's nearly impossible to say like, I need to know all the ins and outs of ADP versus UKG versus Workday and multiplied by a gazillion. But it's a lot easier to say like, all right, really there's like three buckets of competitors that you're going to come up against. There's your legacy payroll providers — they've been around for 30 plus years, they've largely grown through acquisition, here's like the common pain points that are going to happen. Anything that starts with "pay" or ADP falls into that bucket. Then there's like your modern HCM platforms who are awesome, like your Gustos, your Bamboos — customers will be on these, but here's our overall competitive playbook against them. And then here's how we do that against PEOs.
And the more I find we bucket, we allow sellers to do a bit of the pattern recognition of like, I don't know all the ins and outs of this specific provider, but I get structurally where the problems are going to be. And then we get them really good at de-positioning and trap setting.
Alex Kracov: Curious how you communicate all this to the AE teams. Do you have a bunch of battle cards that the enablement team or maybe your product marketing team is managing? Or is it more live training sessions?
Jonas: Yeah, yes, yes. I mean, if you looked into our Confluence, we have so many different pages on our competitors — battle cards, keeping them up to date, making sure that we have kind of the right information there. The fun thing about competitive intelligence in general is it's just constantly adapting. Where you were six months ago, you're going to have to completely change. If you're listening to enough Gong calls, you're going to start seeing like, you know what, this competitor who we had really good win rates against — they're attacking us in a new way. It's like, we need to come up with new objection handling now that we didn't have six months ago. So it is constantly evolving.
One, we've benefited from having a small but mighty competitive intelligence team that literally does nothing all day but think of all these things. They don't sit within my group in enablement, but they are as close of a dotted-line type partner as we could possibly have. We're working with them on the training, the content. They produce really helpful month-by-month insights on just our win rates against every competitor in the set, and then trend lines of like, is this trending up? Is it trending down? Are our programs actually delivering the results that we're hoping they're delivering?
And then the last thing I'd say is a lot of this is actually built into the core Rippling value props that we communicate with customers. If you look at our first call deck — which obviously I can't publish here — we get a lot of those verbal nods from customers because this is their life. They live with all of these different scenarios of working with the legacy HR and all the pain points surrounding that, or having the kind of discontinuous Frankenstack that they stitched together. The better we can articulate the pain of their current-day scenario and then show them how Rippling is fundamentally different, the better off we are in kind of kicking off that evaluation.
Alex Kracov: Makes a lot of sense. Alright, switching gears a little bit. Obviously onboarding is incredibly important. You've gone from 300 to 2,000 sales reps — you've been onboarding a lot of folks over the years. Can you walk us through what that journey looks like? If I'm a new AE starting at Rippling, what does my onboarding program kind of look like?
Jonas: Yes, I think onboarding is some of the most table stakes things that any enablement function has to nail. Like if you're an enablement team and you don't have ridiculously good control and insight into the strength and performance and health of your onboarding program, stop what you're doing right there and make sure that that is in a good spot — especially for fast growing companies like Rippling where we've been hiring, on average, like seven to 900 new folks per year in the revenue org.
So the first thing you would see in our onboarding is it's hyper specialized — surprise, surprise. I think we have 65 different tracks based on the sales role that you are in. Down to this level of specialization of like, you are a mid-market product AE selling our IT cloud products — that's going to be a slightly different path than an SMB IT AE selling IT products. And obviously completely different than the version of that for spend. And then completely different for the version of that person doing that in Dublin. So it gets into like 4D Rubik's cube territory pretty quickly. But again, this has been kind of the necessity as the business has grown, because going back to the idea of the peanut butter approach — you're not going to drive optimal outcomes and get people ramped up and hitting their numbers and building pipeline and closing by doing a totally generalist base layer of onboarding.
So depending on the role, it'll be between four and six weeks. The key thing that we've found in that specialized model that I think is super important for other enablement folks is figuring out the key milestones of the deal that that seller will have to execute once they're actually customer facing. Find the five core milestones and bake those into weekly certifications. Basically say like, look, in order to be a successful AE, you have to nail the first call discovery and demo that you're going to do. So our first certification is all going to be pointed at that. And then you need to figure out all of the training content that gets people ready for whatever that cert is. And if they're good at the cert and they pass that, you're like, cool, milestone done. I now feel good about putting this person on the phone and having them actually go and execute this crucial part of the sales process.
And that's largely the way our onboarding looks. It's kind of like chronological deal flow starting from initial discovery, ending with closing, and then a lot of inspection and certification that they can actually go out and articulate the things and do that in a real world setting. And once they get five checks, let's put them on the phones. By no means are we expecting them to be fully finished products, but we at least know we have an MVP — someone who is ready to be customer facing, at which point we can start transitioning to post-onboarding, manager coaching, things like that.
Alex Kracov: Makes its own sense. And then who is actually designing the curriculum for all of those different tracks? Do you have like one or two people who are just in charge of onboarding at Rippling or is it all of those specialized enablement people responsible for their own segment — like they're full stack enablement people who do the onboarding and post?
Jonas: Yeah, going back to first principles, it's like push decision-making down to the edge. So in terms of the content — like, what's the playbook, how do we get you really good at practicing, what's the right level of certification — that's decided on by that specialist PM and then obviously sales leadership. They're driving a lot of that input and content into the learning paths.
And then on top of that, we have a couple of people who actually administer all of the learning paths because we're hiring so much. If I had my specialized embedded PMs also doing onboarding and all the training, like that would eat up 70% of their time based on the amount that we're hiring, and they wouldn't be able to do that full stack. So they have heavy input on the decision-making along with sales leadership, but the actual administration is handled by a different team just to make sure that that team is freed up.
Alex Kracov: Makes sense. And is the training e-learning? Are you getting everybody into a room and talking about things? Is it role play?
Jonas: All of the above. But my general philosophy is that the best way to learn things is to, one, have it modeled for you — what good looks like — by someone who's really good at it. So oftentimes the person doing the training is an exemplar from the field. Who's our best mid-market rep? Who's our best mid-market manager who just got promoted? They're the ones demonstrating.
And then it's like, you need tons and tons of repetitions and at-bats to get good at those things, especially if you're new. So building in that time for practice, building in the time for role play, making sure people can go work with your managers. We generally say, if you can say it out loud four or five times, you're going to own it, you're going to make it your own. But the first time it comes out of your mouth, it's never good. So building in a lot of time for practice within onboarding is crucial, because you could have the best async content and e-learning in the world, but if people aren't actually doing the thing and taking those swings, they're not really going to get better at it.
Alex Kracov: And then how does the manager play into all of this? Like are they along the way with onboarding and working with their new team, or is it more like, go through onboarding and then you get passed off to your manager and your manager's there to reinforce all the things you learned?
Jonas: Yeah, I think the latter thing that you articulated is like a complete recipe for failure. I've dealt with — and there was to an extent this was kind of the modus operandi when I started at Rippling — managers like, yeah, cool, just hand me a fully formed new hire in eight weeks and they'll just start hitting numbers. You're like, no, man, this needs to be co-created and co-built. So I think the first thing that's important is those frontline managers need to have really strong input into the actual content that's being trained. And as I just said a second ago, oftentimes they're the best people to have in front of a room because they're the subject matter experts. They're the ones who actually have the respect of the team. And if you allow them into the building process, they're going to be a lot more bought in.
And then the second thing that I think is really important is there needs to be a concurrent manager learning path for every sales rep learning path. And I don't mean like when you're onboarding a new manager they get specific leadership training. I mean the manager needs to know week by week what they need to do to support their new hire's learning — make sure they're hitting the milestones. So they have their own checklist that we've helped co-create with them. And I just think the more skin that managers have in the game, the more they feel like it's their responsibility to properly onboard people — which by the way, they have ultimate skin in the game; if their team hits quota, whether they're good or not, that's on them. But really working them into the process is going to meaningfully drive results for your onboarding program.
Alex Kracov: Alright, so we've talked a lot about trainings, but at the beginning you sort of said, okay, trainings are just a step along the way. Enablement teams need to build more towards the actual outcomes of the revenue organization. So how do you think about that?
Jonas: Yeah, that's a good question. After all that talking about training — I mean, I do think from a new hire perspective you obviously lean a little bit more training heavy because you're starting with somewhat of a blank slate. But especially on the ongoing material, here's what I hate or what I think is a recipe for failure: an enablement setup where you're like, hey, we have a weekly enablement slot with the sales team, let's fill it with a training. And you're like, well, what should we train on next week? I don't know, let's do discovery. And the week after that, let's do multi-threading. And the week after that, let's do prospecting. And it's just these random shots in the dark.
And even if the content is fantastic, even if you are the Michael Jordan of sales trainers, you're going to have a muted impact by not having deeper focus on the outcomes that you're looking to drive. So when I say training's overrated, what I mean is all the focus on putting together these perfect trainings should get redirected to figuring out with sales leadership — what are the one to two outcomes that we are looking to drive amongst the sales team — and then putting a lot of the organizational muscle behind driving those over a longer period of time.
So it's like, all right, for March and April, let's just focus on multi-threading. We know that in deals where we get senior leaders involved, we have 75% higher win rates. Let's get everyone on board with that. It'll usually start with the training. But the thing that I find is most important is the pull-through, actual behavior change piece of that. Because all the training does is relay the information, which is usually forgotten a couple of days after. But all the activities after the training — whether it's let's listen to Gong calls, let's find out who's doing this really well, let's make sure there's visibility into dashboards, let's build a library of what good looks like, let's do some individual coaching and arm the managers to be a force multiplier — if you put a lot of the effort on that stuff rather than just the initial origination point, you're going to drive much better results. And also you can then point back at the actual changes that you're having as an org.
Alex Kracov: And I'm curious, how does that relate to your own success metrics as you think about the enablement function and you're talking to your boss and saying, hey, I'm doing a good job? Do you point to those same outcomes — hey, we increased close rates, enablement's doing its job?
Jonas: 100%. I mean, I think if this is one of these always-on motions, it becomes super easy at the end of the year when you're doing your annual self-review of like, what did we actually do this year? And you're like, well, we measure every program. And by the way, not all of them are going to be successful. Can you bat like .500, .600 on these programs? You're awesome. That's great.
I think my intuition is a lot of teams don't do it this way because they're somewhat afraid of being on the hook and having it proven that your enablement didn't work. And then they're like, ugh, I don't want to be in that scenario where we tried to do something, we measured it and it completely failed. And I think that natural preservation mechanism around that is like, let's not measure. Let's just — here's what we should measure — let's measure sentiment leaving the training. And that way, if we only measure that, we can say we delivered an awesome training. Is it our fault that it didn't lead to results? Like, who knows, there's a million things out there. But it's like, no — it's better to go out on a limb, try to have a little bit more skin in the game and really align with leadership on what's going to be important in terms of driving that for the team.
Alex Kracov: Not to get too enablement nerdy — what's the Kirkpatrick method?
Jonas: Not to get like too enablement nerdy on you, but there's the Kirkpatrick method for measuring enablement. There's four layers to it, and they go in order of value back to the business. So the least valuable — but the one that people do the most — is sentiment, which is like, did the employee like the training? The second one is knowledge: could they pass a knowledge test, or if you certified them, could they actually display that they know the things that you trained them on? The third — which is tough to do but really important — is behavior: are they actually translating that to customer-facing conversations, are they actually doing the thing live? And then the fourth is on the business results side.
The comfort zone, the safe zone for enablement is sticking in box one. Maybe box two, we certified people, they passed the certification. The elevated ones — the ones that actually deliver the most value — are can we track behavior change and then can we track business results? And one leads to the other. Like the idea is if we want to multi-thread more, we can see if there are more contacts associated with the account, and if so, is that leading to higher win rates?
On the behavior change front, an enablement team's best friend is Gong. I couldn't — it's the one tool where I'm like, if Gong got ripped away, I'm just retiring. Because it's the only way to measure behavior change at scale. You can really see day by day — is the training actually taking root and translating into a difference in behavior? And if we see that, that's kind of win number one on its own. And then it's like, well, let's see if our hypothesis was right that multi-threading more, which we are seeing happening, is leading to win rates. But oftentimes what I would direct an enablement person to is just focus on the behavior change. If you can actually prove that's happening, then the lagging indicator is you'll see if the hypothesis is true or not.
Alex Kracov: Super interesting. Alright, switching gears. Wouldn't be a podcast in 2026 without talking about AI. I'm curious how you use AI both for the enablement team itself at Rippling, but then potentially more interesting is the sales team at Rippling. What are they doing, and how are you enabling them to use all these different AI tools?
Jonas: Yeah, we have to talk about this. It has changed a bunch over the last six months, but I could say we've definitely taken a lot more of a role in orchestrating sales workflows with AI over the last six to 12 months, in partnership with our fantastic RevOps team. It would be completely unfair for me to try to hoard a lot of the credit for what we're delivering without mentioning them because they're doing a lot of the building.
It's kind of gone in a couple of phases for us. So phase one was like, we have all these tools, all these tools have their own native AI features. Let's use those and actually make sure we're getting the use out of Outreach's AI or Gong's AI or whatever else. But a lot of those are siloed just to that specific tool. In my mind, the next layer and the thing that I think would be most important that we've been focusing on is how do we figure out the orchestration that oftentimes lives in between the tech stack to make sales reps' lives way easier.
One thing we did here — even though it was kind of painstaking, I think it was really important — is we did a time and motion study.
Alex Kracov: What's that?
Jonas: You literally have your enablement team observe a day in the life of a seller, like a full eight-hour day, and do that over and over again. It was super old school. How much time did you spend preparing for your disco call? That was 15 minutes. How much time did you spend inputting info back into the CRM based on the call? That was another 15 minutes. How long did it take you to do CPQ and a quote? That's like an hour. And you could basically roll that up to figure out where the slices in time go and how much time doesn't go to actual selling activities.
And then once you put it on a slide like that and put it in front of sales leaders, oftentimes it's like a total holy crap moment. They're like, how many meetings? That's like — and just quantifying it is so powerful. Because once we did that, we just came up with a full stack rank of all the waste in the system — of which there is a lot — and this isn't impugning our sales team, this is like the processes that we've set them up to go and do. But once we did that, we were able to go work with our RevOps team and they're like, all right, how do we take pre-call research from 15 minutes down to 30 seconds with AI? And how do we take the post-call CRM updating down to zero seconds? Because we can just pipe Gong right into Salesforce and automatically update those.
Or it's like for us in Rippling, with such a complex deal cycle — BDR passes to AE, AE brings in SC, SC brings in PAE — there are so many of these handshakes, oftentimes which require like, let's meet for five minutes, let me write up a 10-minute Slack to tell you what's going on in the deal. It's like all of that's now automated. The second you're bringing in a PAE for spend, a deal brief goes to them with everything they need based on the Gong transcripts. So there's just so many of these breakage points that drain the life and time and energy out of your ranking fire seller. And we're just taking our way down the list with RevOps at this point.
Alex Kracov: Yeah, I mean, that's a great exercise everyone should do. It's worth it. That's the only way you figure it out.
Jonas: 100%. It's helpful to figure out the time and it's also helpful just to rally and cry. Because once you roll it up, it's just a number that you're like, we need to bring this number down.
Alex Kracov: Yeah. And the other interesting dynamic is Rippling itself as an AI platform. I know you just released Rippling AI last week and that was an awesome launch. How do you think about enabling reps to actually sell AI capabilities? Because I think one of the interesting dynamics with these products is they're like iceberg products — everyone has a chatbot, and it all sort of feels the same at the beginning, but there's a lot of different complexity underneath.
Jonas: There's a lot there. I think to your point, if you're a company and you're not talking about AI, your product marketing team should all be fired. So there's this wall of noise out there about that. And the main thing we've been focused on since this launch is obviously equipping our sellers to go out there and sell it. But the differentiation piece has been crucial here. Because if customers at the end of the day go and say like, cool, Rippling has an AI chatbot and that's just like Salesforce's AI chatbot or whoever, then we have deeply failed from an enablement perspective.
Because it's our opinion that our product is highly differentiated. And the reason for that — not to get back into the product pitch — but going back to the very beginning: AI runs on data. Your AI is only going to be as good as your underlying data sources. And if all your underlying data sources are siloed in 12 different point solutions, you're not going to be able to do any of the interesting cross-product AI queries and workflows that would really be impactful. And that's really the unlock with Rippling — all of the data lives in one place, it's all appended to the employee record, and because it all lives in Rippling, you can of course answer basic questions, but then you can also do really cool workflows, build really cool reporting, answer questions about your business that you would never be able to do with more point-solution-oriented AI.
But the real question is, can we get our sellers to explain that to customers? And can we get customers to believe it and see it and make it happen? So I don't know, we're a week into that — I'll tell you how we did in a month or so. We're super excited about the launch.
Alex Kracov: Yeah, I think it's a super interesting dynamic that we're all trying to figure out. I heard one of the founders of Intercom talk about how they give their customers a list of questions to ask their chatbot and competitor chatbots — and there's a lot of gotcha questions in there that they can only answer with their data model. That's a good idea.
Jonas: That's a good trap.
Alex Kracov: All right, I'd love to talk a little bit about your personal journey. You run a giant enablement team in a really big organization. How did you make that leap from kind of an enablement practitioner to a senior leader of other enablement people?
Jonas: Yeah, it has been a ton of fun learning and growing within the overall functional maturity of enablement. Where enablement 10 years ago, people were still arguing whether it belonged in product marketing or belonged in sales. It has been a rapidly developing function and it's been really fun to see how that's developed over the 10 to 15 years that I've been part of it. But fundamentally on my personal journey, it all started within sales. It was pretty much my first job out of college. I think it's the best job in the entire world if you are graduating from college and you're not an engineer or mathematician — get into sales. Learn just executing at a business level.
And I did that for a number of years and kind of moved my way up through the ranks and was managing teams. I was later managing really large teams — probably earlier than I would have anticipated, running a 150-person sales floor — and really had to learn how to get people with no sales background functional at sales and hitting numbers in a short period of time. And that's kind of where the light went off in my head: I kind of like doing this part of the job the best. Like being a sales leader, but I really liked seeing people improve — seeing that person who was struggling to hit their number reach quota for the first time, start walking around their office with that renewed confidence. It was just so cool to be able to do that and get people so much better at their job. So I was like, oh, this is actually a function. People get paid to do this. And I've kind of been on that journey ever since.
Alex Kracov: And what do you think has made you successful? What advice would you give to somebody who's earlier in their career and wants to be a big-time enablement leader?
Jonas: Yeah, going back to specializing — this might be self-serving since this is my background, so take it with a grain of salt — but I do think if you actually want to get into a career in sales enablement, you should start off your career in sales. Do the job that you are hoping to make better. I don't think it's impossible to be a successful enablement person if you've never sold. I just think it's way, way harder. Because developing that seller empathy, really understanding what it's like day in the life as a BDR, as an AE, as an AM, as a manager — that's probably the best experience you can have. Really understanding what the day-to-day is of a frontline sales manager, which is in my estimation the hardest job in all of business. Learn that, understand it. And once you can develop that deep understanding and empathy for it, I think it just gives you the pattern recognition to really understand what's going to be impactful and what won't.
And the more you can do that, the better you're going to be able to relate to sellers, to sales leaders. And oftentimes that's going to be the thing that unlocks you in your career — how do we grow the enablement function, how do we add more headcount to it? There's only one answer: be successful at sales, but also prove value back to the people who are making those headcount decisions, which is largely the VP of sales, CRO, whatever it is. And if they're the ones saying yes, we need more versions of that person because they are so additive, you're going to grow your function. So it's really about making sure that you can go and prove that value back to the business.
Alex Kracov: I'd love to end today's conversation with a question I'm personally very curious about. What's it like working in a Parker Conrad organization? I'm a big fan of him as a CEO, but he's also a very intense CEO in a good way. How does that impact you, the go-to-market team, enablement?
Jonas: Yeah. One day somebody has to write a book about the Rippling culture because it is unique and special and it stems from Parker. Obviously culture is like a diffusion from your most senior leaders and of course your founder CEO. So a couple of things that are unique about Rippling culture that I think have led to our success and are things that I absolutely love about working here.
First things first is just the pace of execution. Every software company in the world says it's fast. And then people start at Rippling and they're like, whoa, the treadmill is at 25 miles an hour and everybody is sucking wind. And I think there's almost like an intentional — our COO, Matt McKinnis, has talked about this — the engine should always be right below the red line. You don't want to completely overheat it, but in a very purposeful fashion, a big job of leadership is driving that pace of execution, especially as you're scaling. Because there's such danger of going from a thousand employees to 5,000 employees and then just everything becomes bureaucratic and slow. And thankfully that has not been the case at Rippling over the three to four years that I've been there.
So the pace is one. The second is there's a huge burden on leaders to be deep, deep experts and to actually do the thing. One of the fundamental principles that Parker has instilled in the org is this idea of "go and see" — which is, if there's a problem, if something's wrong with the business, the leaders need to completely take that to ground and go in the boiler room and turn on the flashlight and find all the cockroaches and do the actual thing to understand what that problem is. And that could end up being listening to a thousand support tickets or listening to a hundred Gong calls. Do the dirty, horrible work to figure out what is wrong, and then you can go fix it. And that's just been completely distilled into the overall operating rhythm of every employee in the business.
There are a lot more Ripplingisms, but those are a couple that I think make it super unique and fun to work here.
Alex Kracov: I love it. And I love the idea of just diving deep. You can only make change if you actually understand the actual problem. Thank you so much for the time today, Jonas. This was a lot of fun talking to you.
Jonas: I appreciate it. Thanks for the invite. It's been fun.
