Morgan Kassel never planned to be in enablement—she didn't even know it existed. She was a quota-carrying AE who kept sneaking away to coach junior reps, getting more satisfaction from watching their names go up on the leaderboard than her own.
A nudge from a friend (who happened to be standing up Vanta's first sales team) changed everything.
In this episode, Morgan joins Alex to share what she's learned being part of the team building and scaling a world-class enablement program inside a hypergrowth company.
Enjoy the show!
Alex Kracov: So you spent almost a decade in sales, but then you started freelancing sales coaching on the side. Like what made you want to coach reps instead of sell?
Morgan: Yeah, so I worked at a company where every time you made a sale, you know, we're all in the pit together. This is pre-pandemic. So we're all in the pit together. The gong goes off on the board. The bell rings, you know, everybody stops what they're doing and is applauding. And I'm the one that's like literally hiding under the desk, hated the attention, didn't really, I liked sales because I like the relationship building. I like helping people, but I really didn't like that kind of spotlight. What I did find so fulfilling is when other reps would, you know, new hires would start or more junior reps would start, I loved helping them. I got so much fulfillment after, you know, seeing their name go up on the board in the background. I am like the loudest person in the room cheering for them. And so I, to be honest, Alex didn't even know that sales enablement was a thing.
We never had sales enablement at any sales org that I worked in. It was always you learn from the people around you. So I didn't know that coaching was a thing that you could do as a career. I thought it's just reserved for managers to do with their reps. And I had a friend who was like, hey, do you want to coach some folks on the side? You know, I know you love to do it. This friend happened to be Eric Martin, EMART — the famous EMART who started up the sales team at Vanta. He's like, you know, I'm starting up the sales team at this little startup and I could really use some other, you know, AEs to just lend a hand and, you know, maybe one or two hours a week, just listen to some calls, do some role plays with, you know, these reps that I'm hiring. I'm like, sign me up. And I loved it and the rest is history. I ended up doing it full time. I literally asked Eric when I joined Vanta full-time: so what's my title gonna be? Sales coach? And he's like, that's not a thing. It's called sales enablement. I'm gonna help you for your resume. It's sales enablement manager. I'm like, cool. I think that sounds about right for what we're gonna be doing here, but that's how I fell into it.
Alex Kracov: And like, are those early coaching sessions — like when you're freelancing with different reps at Vanta and some of the other companies you were working with — what do you do in a coaching session with a sales rep?
Morgan: Yeah, so obviously it's going to be way more around skills than it is around product or proficiency in a certain industry. I wasn't a compliance expert, nor do I play one on TV now either. I certainly didn't know the ins and outs of products that the reps I was coaching at other companies — I couldn't coach them on that. What I did know is the principles of just value-based selling, right? Which is, you want to get really quickly to the matter of what your prospect cares about, right? What's in it for them? And then you're gonna tailor your pitch of your product to exactly meet that need. And that's what I really stuck to — those selling principles. So early stage coaching is me watching Gong calls, watching recordings, coming to a live session with some notes on, you know, again, I don't know much about the product side of what you're doing, but you seem to run into this objection a lot or you seem to talk a little bit versus asking a lot in this particular segment, let's kind of talk about that. So I think it almost helped in a way that I didn't have the product knowledge for these folks because we could really just hone in on the skill.
Alex Kracov: And I mean, yeah, value-based selling is universal across — it doesn't really matter about product. I mean, I think what's so funny about it, it's not even about selling the product. Like that's always what was so weird about for me as a founder building a product, I always sucked at this. It's like, I just want to show you my product. And then it's like, it's not even about that, which is so unintuitive.
Morgan: Exactly. And you just start to remember the things that you were told by your manager — the person in control of the call is actually the one asking the questions, not talking so much, but asking more. And so you pass that along to the reps too. So yeah, it was just very universal selling skills that I was working on in the beginning.
Alex Kracov: And like, does somebody get better at value-based selling? Is it just asking the right questions? Is it as simple as that or is there more to it?
Morgan: Yeah, I think asking the right questions is obviously a big part of it. I think it starts even before that, though. You need to do a lot of homework on who it is that you're talking to and really suss out why the hell would they care, right? I remember this acronym from earlier in my career: WIFM. Have you heard of that, Alex? What's in it for me? Really, it starts with the research before you even get on the call — what's in it for the customer, or the prospect rather? Why would they care? What challenges is this helping them solve? What goals is this helping them achieve? What needs is this checking the box on for them? It starts way before the call using research and insights. And then from there you get to kind of prepare. Okay, then based on that, these are the questions I'm going to ask to get them to share those pains, those goals, those challenges. And then again, it's all about tailoring, right? Doesn't matter if I've asked you the best questions in the world, Alex — if I didn't tailor my pitch accordingly, you're gonna be like, who the hell is she? She's not listening to me. She doesn't understand my business. I'm going elsewhere.
Alex Kracov: Let's transition and talk about Vanta. So in December 2021, you joined Vanta full-time as a sales enablement manager. And I've heard your CRO, Stevie Case, describe the sales team as like the wild west at that point. Like, what was it like from your enablement perspective? What was the sales org like when you first joined?
Morgan: Yeah, very accurate. First of all, much smaller. So at the time, we could do a lot more of this just kind of one-on-one ad hoc scale. Scaling what we were doing wasn't even in my mind yet. I'm sure it was in Stevie's, but it was — how do I phrase this politely? It was a very reactive enablement program versus proactive. We had like a standing weekly session where it was just flavor of the week: hey, what objections are we hearing this week? What new competitors are we hearing about this week? What new product are we releasing this week that we can start to kind of tease out? It was super reactive. There was not really a strategy behind it, to be perfectly honest with you. And it was really designed to help get folks just up to speed as quickly as possible so that they could go to market. And by the way, we didn't really have competitors back then. So it was a different ballgame. I would agree with the wild west statement.
Alex Kracov: And so you're sitting in this weekly meeting — and I've been in those — where it's like, okay, how do we position against this random thing that pops up? Or we have this new feature launching. How does that enablement program start to form? From that weekly meeting, how do you bring it to the field?
Morgan: Yeah, so before that weekly meeting, I'm basically meeting with the sales leaders on the team going, hey, what do we want to focus on? What's a pain point this week? What's a gap we're seeing this week? Then immediately — I'm someone who likes to show versus tell. So rather than me sitting there for 30 minutes telling AEs "this is how we should respond to this objection," I'm gonna go watch game tape and I'm gonna find an AE who is tackling that objection like a rock star and I'm gonna put them on what I like to call — we created, well we didn't create it, ESPN don't sue me — Sports Center Top 10. We would kick off every enablement session with what is that kind of theme of the week and I'd find Gong snippets that were related. Awesome discovery questions, awesome rebuttals, just anything that we really wanted to spotlight as best practices, so that the reps could learn from each other. That's something that has not changed. We still do Sports Center Top 10. But obviously the rest of the program has evolved quite a bit.
Alex Kracov: How did it evolve? Are there clear stages in your head of how it evolved? I know Vanta is at a crazy scale today — how do you think about that evolution of the enablement program and the sales team?
Morgan: Well, first I have to shout out — we hired an enablement leader to really help put a strategy in place. Me not having an enablement background and just sort of having this coaching background, that was a big part. So I'd be remiss not to mention that. But in terms of strategy, a couple things that we did pretty quickly. First of all, you know Vanta — we are truly a rocket ship when it comes to development. Still to this day, I mean, we released over 300 features in 365 days last year. Like that's no joke. In the beginning it was kind of a one-size-fits-all product. It was like "SOC in a box" is what we sold. So obviously as we started to innovate more and add more products and features, we realized this one-size-fits-all onboarding and ongoing enablement program wasn't gonna cut it anymore.
So we started to really get more specialized in terms of role-specific enablement and also segment-specific enablement. For example, the upmarket customers that we sell to — the big enterprises — they have completely different needs, different pain points, completely different goals when using Vanta than a startup who just came out of YC and is just looking to get their first compliance framework in the box to get that first big customer in the door. Totally different. So therefore we need different enablement programs to address those skills. You might need more advanced skills for those enterprise sellers versus the early stage or startup segment. They're selling a different value proposition — the entire value driver for Vanta is totally different for downmarket versus upmarket. And so that was one thing we started to do really quickly.
We also started to grow globally. So what does this look like for the needs of our Dublin and London offices? What does this look like for our Sydney offices? Are there any regional nuances we need to account for? I mean, a CISO in EMEA is actually quite different from a CISO in the US. So addressing those needs, making sure that the reps in those regions are trained on those personas accordingly — that was super important.
Alex Kracov: I think one of the hard parts about Vanta — the subject matter is pretty high stakes and intimidating too. Like a CISO is a pretty serious person and it's not just about "this button does this or that," but you actually have to train on what is SOC 2 compliance and ISO and all these different things. And it's pretty in the weeds stuff. So I'm curious how you think about that balance of training reps on value selling, the actual product, and this domain expertise. How do you think about that?
Morgan: I love this question because it allows me to sing the praises of our teams. We want reps here to absolutely know enough to be dangerous, right? We're going to give you the basics so that you know what I like to call compliance alphabet soup — SOC 2, GDPR, ISO 27001, all of that. But there are a lot of nuances, especially as organizations mature and get more complex. There's no way an AE with excellent selling skills right out of the gate is also going to be able to diagnose some of these complex compliance issues. So we have GRC subject matter experts in house, and we really teach sellers from day one at Vanta: you need to be using these folks. We don't expect you to be the expert. Know enough to be dangerous. Know why someone would want that framework. Understand at a baseline the challenges of pursuing that framework. But it starts with asking them about their experience to validate your hypothesis, and then number two, team selling — "win as one team" is a Vanta principle and we take that very seriously. We don't expect you to close these deals by yourself. And CISOs can sniff that out like that. If you are just using jargon and you don't actually know what you're talking about, they're gonna be the first ones to call you out.
Alex Kracov: Totally. I mean, what you're describing — it's like fancy sales engineers who know real compliance stuff.
Morgan: Yes, sales engineers absolutely too. And solutions engineers — big part of that team as well. Solutions engineers more on the Vanta side, the GRC SMEs more on the compliance side. These are folks that have worked at the big audit firms, managed service providers, consulting firms, et cetera.
Alex Kracov: So Vanta is obviously a tremendous company and has gone through hyperscale while you've been there. I think it went from like 200 to 1,000-plus in your time. And I'm sure onboarding was critical — just bringing in all these new reps and teaching them all the things we're talking about. Can you talk about how that onboarding program scaled and evolved? What broke along the way, and what's still constant today?
Morgan: Absolutely. Our onboarding program in the beginning was a little slapstick. We basically said, okay, what are the different calls that you would have in the sales process? Let's mimic those and get you prepared for these calls. What we forgot to do is what happens in between, and before, and after. And so what we've been able to do now is really expand it. We certify — still to this day, and we started doing this at the beginning — what we call a discovery certification and a demo certification. Those are great. We still do those. Managers certify their reps to make sure that they are up to snuff and ready to take calls.
But now what we've added is a prospecting / pipeline gen certification as well. Because it's not just about the sales process with your customer — it's about what comes before. Pipeline gen is not going anywhere. We don't hit our goals without outbounding. And so that has become a big part of onboarding. Not just leaving it up to managers to put the pressure on to outbound and prospect, but really building that in — giving them that fundamental framework to follow in the beginning. What are the tools you should be using? How should you be tiering and prioritizing your book of business? What modes of communication work well and why? Multithreading — really making sure they have that solid foundation down.
Another thing I'll say: we don't just rely on live enablement anymore. We've incorporated a lot more e-learning. There are different learners who like to learn in different ways. Some love e-learning and would rather have only e-learning. Some hate it and would only want live. We try to meet everybody in the middle. What we do is use e-learning as a foundation for knowledge transfer — if I just need to give you knowledge, like when to use X versus Y framework, that's just knowledge I need to give to you. If it's a skill that we need to practice, that turns into live enablement. And it's not just one-off. We've built a lot of teachbacks, reinforcements — kind of a flipped classroom approach. Maybe you learn the basics of something via e-learning and then it's reinforced in a live activity that's engaging and brings it out of the theoretical and into a real-world application scenario.
Alex Kracov: Is that like a formal recertification, or is it more informal?
Morgan: Yeah, so depending on what it is. If we were to launch a brand new product tomorrow that was huge and could be sold standalone, you bet everybody would get certified on that new product and how to sell it. We also re-certify when we update things like our entire pitch deck. We actually did certifications when we updated our pricing and packaging model too. So if it's a big enough tier one initiative, of course they're gonna get recertified.
Alex Kracov: And is that like the rep goes into a scary room with Stevie and you're judging them like a panel?
Morgan: First, you put a bag over their head. No, I'm kidding. So it can take many forms. Some certifications, we say go out and try this in the real world — try this new sales deck, pitch this new pricing package with a real prospect, and then we're going to go back, grade it, give you feedback. Other times it's a role play with either me on the enablement team or their frontline manager. We come up with some sort of scoring rubric where we've calibrated it together across leadership and enablement to make sure everybody's grading along the same lines. So it's usually one of those two: either live with feedback post, or a mock call.
Alex Kracov: What does your relationship look like with the sales team today — sales leadership and the AEs themselves? Are you meeting with sales leaders to figure out what the priorities are? How do you think about the balance between your different constituents?
Morgan: Yeah, I feel very lucky to work with the team that I do. Having been at the company a long time, I feel like I've earned their trust. So they feel like they can come to me with, okay, these are our top three focus areas for the quarter, we trust Mo to execute on that. But that doesn't mean it's just me. This is actually a big initiative for FY27 right now — manager reinforcement. I could deliver the best damn training in the world and it doesn't matter if a frontline manager is not reinforcing it. And that doesn't start after the training — it actually starts before.
So on a quarterly basis, we align on what the priorities are. Some of these are top-down and some actually come from the data — almost like bottom-up. Hey, we've been hearing from the field that they are struggling to sell this specific package or struggling with this certain competitor. Everybody needs to be aligned on that. If managers aren't bought in that this is a big enough problem to solve and worth taking their team off the floor for, it could be the best training in the world and it still won't stick. So it's a very collaborative relationship. We try to make decisions that are backed by data and not just a hunch.
Alex Kracov: And like, how do you hold those managers accountable? You can't be in their one-on-ones with their AEs.
Morgan: It's a great question. Part of it starts with the managers realizing that their reps' number is their number. Having them bought in a lot of ways hopefully comes naturally — if these are true gaps on my team and this is going to help me get to our goals faster, I better be bought in. A lot of it is also having internal champions who can really start to enforce this with their team, show what good looks like, be a good example, and have the other managers see that it's successful and kind of follow suit. And to be perfectly honest, there are some leadership incentives that map to that reinforcement as well. A lot of what managers are held to isn't just their number — there are usually some coaching metrics they're required to hit. There has to be a carrot or a stick at the end of the day.
Alex Kracov: I guess one of the hard things about being a sales rep is that time is finite. Most of it needs to be spent on prospects — working with buyers, prospecting, doing outbound. They only have so much brain space to digest new information. How do you think about that dynamic and pick your spots as an enablement person?
Morgan: Yeah, I'm gonna say something that my cross-functional coworkers would be horrified to hear, but a lot of what I do is goalie work. You've got marketing, rev ops, product, partners — all these different departments that want to get in front of the same sellers. And if you ask them all, every one of their initiatives is tier one, absolutely.
What we're developing right now — and we're really excited about it — is an intake process. Any cross-functional stakeholder who wants to get something in front of the sales team has to go through this intake process. From there, we match it to: does this directly tie to those big three priorities for the quarter? If not, we go directly to that sales leader and say, hey, this has been requested to be put in front of the sales team's time, it doesn't map to our big three priorities — is this something we should reprioritize, or push back on?
It's not about me being a gatekeeper. It's really about communication across cross-functional teams. We have a bi-weekly meeting where all those different departments get together in one room: what marketing campaigns are coming up, what tools do they need to be trained on, is there a new pitch deck they need to learn. We all look at the calendar and say there are only so many hours an AE can be taken off the floor, so something's got to give. We come together with a recommendation to sales leaders and they make the ultimate call. I find presenting the information with a recommendation is always the right approach. At the end of the day, you're there to drive revenue as an AE — I want to make sure every single minute they're pulled off the floor is for something really valuable.
Alex Kracov: And AEs can kind of snuff out a BS training versus one that's actually going to make an impact, right? You can see it on their faces on Zoom or in person.
Morgan: Oh my God, absolutely. We experienced that with our product enablement strategy. Product really wants reps to digest product updates, but we realized showing them 60 minutes of a slide deck with 25 new products was not the best way to get their attention. So now we built an e-learning component, we built activities to reinforce it and bring it into the practical day-to-day. So it's not that the content isn't important — it's about how do we reframe it, how do we get it in front of them in a different medium that would be more effective.
Alex Kracov: One thing Vanta has had to deal with is a lot of copycat competitors. Vanta pioneered the space, but then a bunch of startups started popping up. And I heard you built the Competitive Intelligence Agency — the CIA. Great acronym. Can you talk about what good competitive enablement looks like at scale?
Morgan: Yes. So I'm very grateful to work at a company where Christina — our founder — from day one has chosen: we will always take the high road. And we really practice that. She said something from the beginning that really stuck with me: we want to be competitor aware and customer obsessed. And I think that is part of the reason we win so much. We do know enough about our competition to know exactly which differentiators to lean into, but we're not going to sit there and talk shit about a competitor for 30 minutes. We want to stay really hyper focused on where is Vanta best suited and how is Vanta best suited to meet your needs.
What that actually looks like in practice: I run the competitive training for onboarding for all new hires. And before we even mention a competitor's name, before we even talk about the landscape, I find it's really important to know where Vanta shines broadly against the rest of the market. What are the things we can really lean on — we're the most automated, the most innovative, the most trusted — and really getting into reps' minds all the different scenarios where they can use those differentiators. So if I have a prospect that really cares about speed, I'm not going to waste my time talking about our support as a differentiator. I want to dial in on the differentiator that's going to be most effective there.
At the end of the day, it comes back to being an expert on Vanta. Then we can ask: this is how Vanta defines automation, this is what Vanta's Trust Center can do for you — I'm curious, the other vendors you're looking at, can they do the same thing? How do they define automation? How do they define continuous monitoring? It's about helping and inspiring your prospects to do more of that discovery for themselves.
And where our sales team really shines is playing offense early — getting in there early, influencing what they should care about so that it gets on their checklist. Alex, they don't come to Vanta going, "I want to work with a trusted proven market leader." They don't do that. We have to get them to care about that early, versus talking shit and going feature by feature against competitors. How do we get them to care about where we shine the most?
Alex Kracov: I think what you said there about influencing how they're even thinking about the purchasing decision — I feel that at Dock when our competitors are somewhat doing that to us. I'm like, huh, I wonder why you care about these three features that they have but we don't. Are those actually that important? I can tell you talked to so-and-so first, and that's how it ended up here.
Morgan: Alex, you might need to get some of my methods in there to start influencing your sales team.
Alex Kracov: All right, I'd love to switch gears and talk about the enablement team itself. I think you've grown a lot over the last year and have different specialized roles. Can you talk about how the team has evolved?
Morgan: Yeah, absolutely. When I started there were two of us and now there's 13 of us. I know a lot of people hearing that would probably be like, holy shit, that team is overstaffed. But we are really specialized because we've realized that the needs of the teams can vary greatly. For example, a CSM — their skills are completely different. But at the core of everything: value-based selling. Our core curriculum, everything is built off of value-based selling. Even for the CSM — value realization for the CSM is the biggest thing at Vanta. Whether you're an SDR, solutions engineer, AE, account manager — whatever your role, it always is going to start with value-based selling. But then the skills in terms of your actual day-to-day obviously vary a lot. A CSM doesn't need to know how to prospect effectively.
What we've done is get specific not just on role-based enablement but also segment-based enablement. The needs of the upmarket AEs are different from the top three priorities of the downmarket AEs. There's definitely crossover, but the teams have gotten so big and the leaders are adamant about having only the most relevant content put in front of their teams — and I completely agree.
We've also been developing a curriculum that really builds upon itself. We have AEs or SDRs who enter the business brand-new to sales, and then some who have a lot of experience and maybe don't need negotiation 101. So we're creating a curriculum where, okay, maybe this new hire can go automatically to the advanced level of this skill training, whereas another new hire needs to start from scratch. In order to build a curriculum like that, you need a lot of content on deck and the help of some awesome instructional designers and AI.
With that being said, we still collaborate a ton. Today I was in a meeting with our enablement team where the post-sale side was talking about multithreading. And I was like, I want to leverage that framework for AEs. And then the SDR manager was like, SDRs should be learning this content too. So we're very transparent about the priorities of each business we support, and that way we're not reinventing the wheel.
Alex Kracov: And does the curriculum always start from the role — SDR, mid-market, enterprise — and go from there?
Morgan: So this is something I'm very passionate about. It really starts with a set of core competencies. Some of those competencies are the same across go-to-market, and then there are a lot that are very different. I think it's really important — even for a startup — to get aligned between your sales leaders and your people team on what are those core competencies? What are the skills that any AE in any enterprise organization should have? As long as you can get alignment on that, then it's much easier to build out a curriculum. And if someone asks for something outside of the curriculum, that's your opportunity to say, hey, sounds like this might not be a big priority — curious where this is coming from. I do my own discovery there.
Alex Kracov: That's where it helps to be a former seller. You can reverse it on them.
Morgan: Yeah, what outcome are you looking to achieve there? Is there another way we can hit the same outcome with a different skill?
Alex Kracov: And one of the things the enablement team just ran was the CKO. You just did one in Vegas, which sounds fun. Can you take us behind the scenes — what goes into putting on a big CKO like this, and why even do it?
Morgan: Oh my gosh. Well, Alex, as you know, we are a mostly remote organization. We do have offices where certain roles come in a couple of days a week, but the vast majority of our company is remote. So an opportunity to all come together is not only welcome — it's begged for all the time across the team. We're a very social company, we love each other, we really want to spend more time with each other. So obviously the obvious reasons to foster culture and collaboration and empathy across different roles and responsibilities. Even just hearing about what others on the team do, having no idea what their day-to-day looks like — that's big.
I can't take credit — enablement can't take credit for all of the planning that goes into CKO because we have an events team that does an incredible job with the logistics. What enablement does is help shape a lot of the breakout content. When you go to something like a CKO, you can expect some main stage content — get really hyped on the products coming this year, what the year will look like from a vision perspective. But then we've got to get really down into our teams and roles. So I work very closely with our sales leaders and sales managers to come up with that content.
Stevie, our CRO, this year really wanted to focus on team selling as a big pillar theme for CKO. So we took that back to our respective teams and put together content in collaboration with the sales managers. And what's unique about Vanta versus other all-company events I've attended is we involve a lot of the ICs themselves. We have SDRs coming up and showing, here's how I work really well with my AE, here are the LinkedIn videos that have gotten me success. We bring them up to speak firsthand on what's working. Sharing best practices is something we do really well here, and a stage like CKO is a great forum for that.
Alex Kracov: And you say CKO — company kickoff — so that's literally everybody? Engineers, product, everybody?
Morgan: Literally everyone. Engineers, product, we even have channel partners that come. I don't know how many more full-company CKOs we're going to do versus just revenue ones — I think next year might be revenue only. We're getting a little big for that even by Vegas standards. But it was so much fun and amazing.
Alex Kracov: All right, everybody in the world is talking about AI and how it's impacting things. How do you think about using this technology from an enablement perspective? Are you using AI at Vanta to help enablement?
Morgan: Yeah, so the way I personally like to think about AI is: AI is not going to replace human-to-human coaching. I don't think a rep ever wants to be coached by a robot. That's best served from a human — like their manager or a peer. But AI is an excellent way to detect or diagnose gaps to coach on. It's almost like enablement and frontline managers' best friend running analysis in the background.
I'll give you an example. Gong — I promise I'm not being paid by Gong to say this, but it is my favorite tool that I use. Gong obviously not only provides transcripts, but they can even auto-score calls. They can really help detect trends in a rep's sales acumen. You can give it a handful of calls and it'll make that diagnosis for you. Is it 100% accurate? Probably not. You're gonna need to validate its hypothesis, but it's an excellent starting point.
Some other things that we've built recently: we use Dust. It's basically an AI bot where you can build different agents, and it has all of Vanta's universe behind the scenes. We've been able to build Dust bots for things like competitive intel — we call it Compete GPT. So let's say I'm in a deal against OneTrust, they care about privacy, the company's 400 people — what are the top three things I should really lean into? What are the differentiators? Or: hey, I'm in a deal against Drata — what are our strengths in our third-party risk management tool versus theirs? We can get really specific there. We also built one for pre-call research. Gone are the days of searching Google for where's their trust center, what frameworks are they pursuing, who's their ICP — this agent pulls it all in like two minutes.
We actually have folks on staff who are solely dedicated to AI for internal use. I'm not even talking about AI in the Vanta product — I'm talking about how Vantans can use AI to do their jobs better. We have multiple folks on staff full time to help us build these kinds of agents and bots.
Alex Kracov: One interesting thing you said is that sales might be like the last category to get automated because it's so personal. But there's a category that's popped up a lot — AI sales roleplay. Have you used any of those?
Morgan: Yes, we use one of those bots — I think it's called Hyperbound, it's like a cold call simulator. So our SDRs who are brand new, it's really helpful for them to take the edge off, to get comfortable being on the fly, being audible-ready. Taking questions and trying to pivot and answer quickly — really helpful for those scenarios just to get some practice and reps under their belt.
Where I'll stand by this: I can tell, as a user, as a prospect for companies trying to go after me, I can tell what emails are AI-written and which are human. There's a reason why our SDRs — more than 20 of them are going to President's Club this year — the ones doing really well are the ones doing that personal, face-to-face, "hey, I'm a human on LinkedIn, I promise" approach. Humans still want to talk to humans. I think there are certain things a bot can really help with — maybe getting a high-level demo overview or giving you pricing. But at the end of the day, humans still want to be sold to by humans. It's just been evidenced by their success.
Alex Kracov: It's amazing how we can spot it so subconsciously, like email copy. They're probably better emails than I can write, but you can always spot something's fishy.
Morgan: Absolutely. Those bots have a great use case for practice, but I don't know that they'll replace what we're doing as humans. I'm not so worried about that yet — but maybe those are my famous last words.
Alex Kracov: Your job's still safe. All right, maybe my final question — if you were talking to an enablement leader at, say, a 500-person company, what would you tell them to prioritize this year?
Morgan: Hmm. First of all, if you're not on great terms with your rev ops team, send them some cupcakes and get on their good side, because they have been instrumental in helping us make more data-backed decisions. When you're really early on at a company, everything gets surfaced up anecdotally. And sometimes the loudest voices in the room can sound like the biggest problems, but maybe it's just one single loud voice. It's so important to always go back to what the data is telling you. Is this really a top close-loss reason for us, or is this just maybe someone loud who wants it for two people on their team?
Also, the folks on my rev ops team have been instrumental in helping build these AI agents we use to make our reps more efficient. So I'd say a tight relationship with rev ops is a big, big one.
Another one: if you haven't already, purchase a Gong or a Chorus or something similar. I stand by this. Reps love to learn from each other. You do so much more effective by showing them a top performer deliver a talk track versus me delivering a talk track in a training. They want to learn directly from each other, and Gong is the best way to identify those people but also identify those gaps. And they're continuing to make the AI components of their tools more accurate. Those would be my top two suggestions if they're not already doing them.
Alex Kracov: Those are great ones. Well, thank you so much for the time today — this was super fun.
Morgan: Yeah, of course. Thanks for having me.
Morgan Kassel is a Senior GTM Enablement Manager at Vanta, the $4B+ security compliance unicorn serving 12,000+ customers.
She spent nearly a decade as a quota-carrying sales rep before pivoting into enablement, first as a freelance sales coach working with AEs at companies like Vanta, Carta, Lattice, and PitchBook, then joining Vanta full-time in December 2021.
Since then, she's been part of the team scaling Vanta's GTM enablement program from a reactive weekly meeting to a specialized, data-driven operation of 13 as the company grew from roughly 200 to 1,000+ employees. Her seller-to-enabler path gives her rare credibility on both sides of the coaching relationship.
Morgan Kassel never planned to be in enablement—she didn't even know it existed. She was a quota-carrying AE who kept sneaking away to coach junior reps, getting more satisfaction from watching their names go up on the leaderboard than her own.
A nudge from a friend (who happened to be standing up Vanta's first sales team) changed everything.
In this episode, Morgan joins Alex to share what she's learned being part of the team building and scaling a world-class enablement program inside a hypergrowth company.
Enjoy the show!
Alex Kracov: So you spent almost a decade in sales, but then you started freelancing sales coaching on the side. Like what made you want to coach reps instead of sell?
Morgan: Yeah, so I worked at a company where every time you made a sale, you know, we're all in the pit together. This is pre-pandemic. So we're all in the pit together. The gong goes off on the board. The bell rings, you know, everybody stops what they're doing and is applauding. And I'm the one that's like literally hiding under the desk, hated the attention, didn't really, I liked sales because I like the relationship building. I like helping people, but I really didn't like that kind of spotlight. What I did find so fulfilling is when other reps would, you know, new hires would start or more junior reps would start, I loved helping them. I got so much fulfillment after, you know, seeing their name go up on the board in the background. I am like the loudest person in the room cheering for them. And so I, to be honest, Alex didn't even know that sales enablement was a thing.
We never had sales enablement at any sales org that I worked in. It was always you learn from the people around you. So I didn't know that coaching was a thing that you could do as a career. I thought it's just reserved for managers to do with their reps. And I had a friend who was like, hey, do you want to coach some folks on the side? You know, I know you love to do it. This friend happened to be Eric Martin, EMART — the famous EMART who started up the sales team at Vanta. He's like, you know, I'm starting up the sales team at this little startup and I could really use some other, you know, AEs to just lend a hand and, you know, maybe one or two hours a week, just listen to some calls, do some role plays with, you know, these reps that I'm hiring. I'm like, sign me up. And I loved it and the rest is history. I ended up doing it full time. I literally asked Eric when I joined Vanta full-time: so what's my title gonna be? Sales coach? And he's like, that's not a thing. It's called sales enablement. I'm gonna help you for your resume. It's sales enablement manager. I'm like, cool. I think that sounds about right for what we're gonna be doing here, but that's how I fell into it.
Alex Kracov: And like, are those early coaching sessions — like when you're freelancing with different reps at Vanta and some of the other companies you were working with — what do you do in a coaching session with a sales rep?
Morgan: Yeah, so obviously it's going to be way more around skills than it is around product or proficiency in a certain industry. I wasn't a compliance expert, nor do I play one on TV now either. I certainly didn't know the ins and outs of products that the reps I was coaching at other companies — I couldn't coach them on that. What I did know is the principles of just value-based selling, right? Which is, you want to get really quickly to the matter of what your prospect cares about, right? What's in it for them? And then you're gonna tailor your pitch of your product to exactly meet that need. And that's what I really stuck to — those selling principles. So early stage coaching is me watching Gong calls, watching recordings, coming to a live session with some notes on, you know, again, I don't know much about the product side of what you're doing, but you seem to run into this objection a lot or you seem to talk a little bit versus asking a lot in this particular segment, let's kind of talk about that. So I think it almost helped in a way that I didn't have the product knowledge for these folks because we could really just hone in on the skill.
Alex Kracov: And I mean, yeah, value-based selling is universal across — it doesn't really matter about product. I mean, I think what's so funny about it, it's not even about selling the product. Like that's always what was so weird about for me as a founder building a product, I always sucked at this. It's like, I just want to show you my product. And then it's like, it's not even about that, which is so unintuitive.
Morgan: Exactly. And you just start to remember the things that you were told by your manager — the person in control of the call is actually the one asking the questions, not talking so much, but asking more. And so you pass that along to the reps too. So yeah, it was just very universal selling skills that I was working on in the beginning.
Alex Kracov: And like, does somebody get better at value-based selling? Is it just asking the right questions? Is it as simple as that or is there more to it?
Morgan: Yeah, I think asking the right questions is obviously a big part of it. I think it starts even before that, though. You need to do a lot of homework on who it is that you're talking to and really suss out why the hell would they care, right? I remember this acronym from earlier in my career: WIFM. Have you heard of that, Alex? What's in it for me? Really, it starts with the research before you even get on the call — what's in it for the customer, or the prospect rather? Why would they care? What challenges is this helping them solve? What goals is this helping them achieve? What needs is this checking the box on for them? It starts way before the call using research and insights. And then from there you get to kind of prepare. Okay, then based on that, these are the questions I'm going to ask to get them to share those pains, those goals, those challenges. And then again, it's all about tailoring, right? Doesn't matter if I've asked you the best questions in the world, Alex — if I didn't tailor my pitch accordingly, you're gonna be like, who the hell is she? She's not listening to me. She doesn't understand my business. I'm going elsewhere.
Alex Kracov: Let's transition and talk about Vanta. So in December 2021, you joined Vanta full-time as a sales enablement manager. And I've heard your CRO, Stevie Case, describe the sales team as like the wild west at that point. Like, what was it like from your enablement perspective? What was the sales org like when you first joined?
Morgan: Yeah, very accurate. First of all, much smaller. So at the time, we could do a lot more of this just kind of one-on-one ad hoc scale. Scaling what we were doing wasn't even in my mind yet. I'm sure it was in Stevie's, but it was — how do I phrase this politely? It was a very reactive enablement program versus proactive. We had like a standing weekly session where it was just flavor of the week: hey, what objections are we hearing this week? What new competitors are we hearing about this week? What new product are we releasing this week that we can start to kind of tease out? It was super reactive. There was not really a strategy behind it, to be perfectly honest with you. And it was really designed to help get folks just up to speed as quickly as possible so that they could go to market. And by the way, we didn't really have competitors back then. So it was a different ballgame. I would agree with the wild west statement.
Alex Kracov: And so you're sitting in this weekly meeting — and I've been in those — where it's like, okay, how do we position against this random thing that pops up? Or we have this new feature launching. How does that enablement program start to form? From that weekly meeting, how do you bring it to the field?
Morgan: Yeah, so before that weekly meeting, I'm basically meeting with the sales leaders on the team going, hey, what do we want to focus on? What's a pain point this week? What's a gap we're seeing this week? Then immediately — I'm someone who likes to show versus tell. So rather than me sitting there for 30 minutes telling AEs "this is how we should respond to this objection," I'm gonna go watch game tape and I'm gonna find an AE who is tackling that objection like a rock star and I'm gonna put them on what I like to call — we created, well we didn't create it, ESPN don't sue me — Sports Center Top 10. We would kick off every enablement session with what is that kind of theme of the week and I'd find Gong snippets that were related. Awesome discovery questions, awesome rebuttals, just anything that we really wanted to spotlight as best practices, so that the reps could learn from each other. That's something that has not changed. We still do Sports Center Top 10. But obviously the rest of the program has evolved quite a bit.
Alex Kracov: How did it evolve? Are there clear stages in your head of how it evolved? I know Vanta is at a crazy scale today — how do you think about that evolution of the enablement program and the sales team?
Morgan: Well, first I have to shout out — we hired an enablement leader to really help put a strategy in place. Me not having an enablement background and just sort of having this coaching background, that was a big part. So I'd be remiss not to mention that. But in terms of strategy, a couple things that we did pretty quickly. First of all, you know Vanta — we are truly a rocket ship when it comes to development. Still to this day, I mean, we released over 300 features in 365 days last year. Like that's no joke. In the beginning it was kind of a one-size-fits-all product. It was like "SOC in a box" is what we sold. So obviously as we started to innovate more and add more products and features, we realized this one-size-fits-all onboarding and ongoing enablement program wasn't gonna cut it anymore.
So we started to really get more specialized in terms of role-specific enablement and also segment-specific enablement. For example, the upmarket customers that we sell to — the big enterprises — they have completely different needs, different pain points, completely different goals when using Vanta than a startup who just came out of YC and is just looking to get their first compliance framework in the box to get that first big customer in the door. Totally different. So therefore we need different enablement programs to address those skills. You might need more advanced skills for those enterprise sellers versus the early stage or startup segment. They're selling a different value proposition — the entire value driver for Vanta is totally different for downmarket versus upmarket. And so that was one thing we started to do really quickly.
We also started to grow globally. So what does this look like for the needs of our Dublin and London offices? What does this look like for our Sydney offices? Are there any regional nuances we need to account for? I mean, a CISO in EMEA is actually quite different from a CISO in the US. So addressing those needs, making sure that the reps in those regions are trained on those personas accordingly — that was super important.
Alex Kracov: I think one of the hard parts about Vanta — the subject matter is pretty high stakes and intimidating too. Like a CISO is a pretty serious person and it's not just about "this button does this or that," but you actually have to train on what is SOC 2 compliance and ISO and all these different things. And it's pretty in the weeds stuff. So I'm curious how you think about that balance of training reps on value selling, the actual product, and this domain expertise. How do you think about that?
Morgan: I love this question because it allows me to sing the praises of our teams. We want reps here to absolutely know enough to be dangerous, right? We're going to give you the basics so that you know what I like to call compliance alphabet soup — SOC 2, GDPR, ISO 27001, all of that. But there are a lot of nuances, especially as organizations mature and get more complex. There's no way an AE with excellent selling skills right out of the gate is also going to be able to diagnose some of these complex compliance issues. So we have GRC subject matter experts in house, and we really teach sellers from day one at Vanta: you need to be using these folks. We don't expect you to be the expert. Know enough to be dangerous. Know why someone would want that framework. Understand at a baseline the challenges of pursuing that framework. But it starts with asking them about their experience to validate your hypothesis, and then number two, team selling — "win as one team" is a Vanta principle and we take that very seriously. We don't expect you to close these deals by yourself. And CISOs can sniff that out like that. If you are just using jargon and you don't actually know what you're talking about, they're gonna be the first ones to call you out.
Alex Kracov: Totally. I mean, what you're describing — it's like fancy sales engineers who know real compliance stuff.
Morgan: Yes, sales engineers absolutely too. And solutions engineers — big part of that team as well. Solutions engineers more on the Vanta side, the GRC SMEs more on the compliance side. These are folks that have worked at the big audit firms, managed service providers, consulting firms, et cetera.
Alex Kracov: So Vanta is obviously a tremendous company and has gone through hyperscale while you've been there. I think it went from like 200 to 1,000-plus in your time. And I'm sure onboarding was critical — just bringing in all these new reps and teaching them all the things we're talking about. Can you talk about how that onboarding program scaled and evolved? What broke along the way, and what's still constant today?
Morgan: Absolutely. Our onboarding program in the beginning was a little slapstick. We basically said, okay, what are the different calls that you would have in the sales process? Let's mimic those and get you prepared for these calls. What we forgot to do is what happens in between, and before, and after. And so what we've been able to do now is really expand it. We certify — still to this day, and we started doing this at the beginning — what we call a discovery certification and a demo certification. Those are great. We still do those. Managers certify their reps to make sure that they are up to snuff and ready to take calls.
But now what we've added is a prospecting / pipeline gen certification as well. Because it's not just about the sales process with your customer — it's about what comes before. Pipeline gen is not going anywhere. We don't hit our goals without outbounding. And so that has become a big part of onboarding. Not just leaving it up to managers to put the pressure on to outbound and prospect, but really building that in — giving them that fundamental framework to follow in the beginning. What are the tools you should be using? How should you be tiering and prioritizing your book of business? What modes of communication work well and why? Multithreading — really making sure they have that solid foundation down.
Another thing I'll say: we don't just rely on live enablement anymore. We've incorporated a lot more e-learning. There are different learners who like to learn in different ways. Some love e-learning and would rather have only e-learning. Some hate it and would only want live. We try to meet everybody in the middle. What we do is use e-learning as a foundation for knowledge transfer — if I just need to give you knowledge, like when to use X versus Y framework, that's just knowledge I need to give to you. If it's a skill that we need to practice, that turns into live enablement. And it's not just one-off. We've built a lot of teachbacks, reinforcements — kind of a flipped classroom approach. Maybe you learn the basics of something via e-learning and then it's reinforced in a live activity that's engaging and brings it out of the theoretical and into a real-world application scenario.
Alex Kracov: Is that like a formal recertification, or is it more informal?
Morgan: Yeah, so depending on what it is. If we were to launch a brand new product tomorrow that was huge and could be sold standalone, you bet everybody would get certified on that new product and how to sell it. We also re-certify when we update things like our entire pitch deck. We actually did certifications when we updated our pricing and packaging model too. So if it's a big enough tier one initiative, of course they're gonna get recertified.
Alex Kracov: And is that like the rep goes into a scary room with Stevie and you're judging them like a panel?
Morgan: First, you put a bag over their head. No, I'm kidding. So it can take many forms. Some certifications, we say go out and try this in the real world — try this new sales deck, pitch this new pricing package with a real prospect, and then we're going to go back, grade it, give you feedback. Other times it's a role play with either me on the enablement team or their frontline manager. We come up with some sort of scoring rubric where we've calibrated it together across leadership and enablement to make sure everybody's grading along the same lines. So it's usually one of those two: either live with feedback post, or a mock call.
Alex Kracov: What does your relationship look like with the sales team today — sales leadership and the AEs themselves? Are you meeting with sales leaders to figure out what the priorities are? How do you think about the balance between your different constituents?
Morgan: Yeah, I feel very lucky to work with the team that I do. Having been at the company a long time, I feel like I've earned their trust. So they feel like they can come to me with, okay, these are our top three focus areas for the quarter, we trust Mo to execute on that. But that doesn't mean it's just me. This is actually a big initiative for FY27 right now — manager reinforcement. I could deliver the best damn training in the world and it doesn't matter if a frontline manager is not reinforcing it. And that doesn't start after the training — it actually starts before.
So on a quarterly basis, we align on what the priorities are. Some of these are top-down and some actually come from the data — almost like bottom-up. Hey, we've been hearing from the field that they are struggling to sell this specific package or struggling with this certain competitor. Everybody needs to be aligned on that. If managers aren't bought in that this is a big enough problem to solve and worth taking their team off the floor for, it could be the best training in the world and it still won't stick. So it's a very collaborative relationship. We try to make decisions that are backed by data and not just a hunch.
Alex Kracov: And like, how do you hold those managers accountable? You can't be in their one-on-ones with their AEs.
Morgan: It's a great question. Part of it starts with the managers realizing that their reps' number is their number. Having them bought in a lot of ways hopefully comes naturally — if these are true gaps on my team and this is going to help me get to our goals faster, I better be bought in. A lot of it is also having internal champions who can really start to enforce this with their team, show what good looks like, be a good example, and have the other managers see that it's successful and kind of follow suit. And to be perfectly honest, there are some leadership incentives that map to that reinforcement as well. A lot of what managers are held to isn't just their number — there are usually some coaching metrics they're required to hit. There has to be a carrot or a stick at the end of the day.
Alex Kracov: I guess one of the hard things about being a sales rep is that time is finite. Most of it needs to be spent on prospects — working with buyers, prospecting, doing outbound. They only have so much brain space to digest new information. How do you think about that dynamic and pick your spots as an enablement person?
Morgan: Yeah, I'm gonna say something that my cross-functional coworkers would be horrified to hear, but a lot of what I do is goalie work. You've got marketing, rev ops, product, partners — all these different departments that want to get in front of the same sellers. And if you ask them all, every one of their initiatives is tier one, absolutely.
What we're developing right now — and we're really excited about it — is an intake process. Any cross-functional stakeholder who wants to get something in front of the sales team has to go through this intake process. From there, we match it to: does this directly tie to those big three priorities for the quarter? If not, we go directly to that sales leader and say, hey, this has been requested to be put in front of the sales team's time, it doesn't map to our big three priorities — is this something we should reprioritize, or push back on?
It's not about me being a gatekeeper. It's really about communication across cross-functional teams. We have a bi-weekly meeting where all those different departments get together in one room: what marketing campaigns are coming up, what tools do they need to be trained on, is there a new pitch deck they need to learn. We all look at the calendar and say there are only so many hours an AE can be taken off the floor, so something's got to give. We come together with a recommendation to sales leaders and they make the ultimate call. I find presenting the information with a recommendation is always the right approach. At the end of the day, you're there to drive revenue as an AE — I want to make sure every single minute they're pulled off the floor is for something really valuable.
Alex Kracov: And AEs can kind of snuff out a BS training versus one that's actually going to make an impact, right? You can see it on their faces on Zoom or in person.
Morgan: Oh my God, absolutely. We experienced that with our product enablement strategy. Product really wants reps to digest product updates, but we realized showing them 60 minutes of a slide deck with 25 new products was not the best way to get their attention. So now we built an e-learning component, we built activities to reinforce it and bring it into the practical day-to-day. So it's not that the content isn't important — it's about how do we reframe it, how do we get it in front of them in a different medium that would be more effective.
Alex Kracov: One thing Vanta has had to deal with is a lot of copycat competitors. Vanta pioneered the space, but then a bunch of startups started popping up. And I heard you built the Competitive Intelligence Agency — the CIA. Great acronym. Can you talk about what good competitive enablement looks like at scale?
Morgan: Yes. So I'm very grateful to work at a company where Christina — our founder — from day one has chosen: we will always take the high road. And we really practice that. She said something from the beginning that really stuck with me: we want to be competitor aware and customer obsessed. And I think that is part of the reason we win so much. We do know enough about our competition to know exactly which differentiators to lean into, but we're not going to sit there and talk shit about a competitor for 30 minutes. We want to stay really hyper focused on where is Vanta best suited and how is Vanta best suited to meet your needs.
What that actually looks like in practice: I run the competitive training for onboarding for all new hires. And before we even mention a competitor's name, before we even talk about the landscape, I find it's really important to know where Vanta shines broadly against the rest of the market. What are the things we can really lean on — we're the most automated, the most innovative, the most trusted — and really getting into reps' minds all the different scenarios where they can use those differentiators. So if I have a prospect that really cares about speed, I'm not going to waste my time talking about our support as a differentiator. I want to dial in on the differentiator that's going to be most effective there.
At the end of the day, it comes back to being an expert on Vanta. Then we can ask: this is how Vanta defines automation, this is what Vanta's Trust Center can do for you — I'm curious, the other vendors you're looking at, can they do the same thing? How do they define automation? How do they define continuous monitoring? It's about helping and inspiring your prospects to do more of that discovery for themselves.
And where our sales team really shines is playing offense early — getting in there early, influencing what they should care about so that it gets on their checklist. Alex, they don't come to Vanta going, "I want to work with a trusted proven market leader." They don't do that. We have to get them to care about that early, versus talking shit and going feature by feature against competitors. How do we get them to care about where we shine the most?
Alex Kracov: I think what you said there about influencing how they're even thinking about the purchasing decision — I feel that at Dock when our competitors are somewhat doing that to us. I'm like, huh, I wonder why you care about these three features that they have but we don't. Are those actually that important? I can tell you talked to so-and-so first, and that's how it ended up here.
Morgan: Alex, you might need to get some of my methods in there to start influencing your sales team.
Alex Kracov: All right, I'd love to switch gears and talk about the enablement team itself. I think you've grown a lot over the last year and have different specialized roles. Can you talk about how the team has evolved?
Morgan: Yeah, absolutely. When I started there were two of us and now there's 13 of us. I know a lot of people hearing that would probably be like, holy shit, that team is overstaffed. But we are really specialized because we've realized that the needs of the teams can vary greatly. For example, a CSM — their skills are completely different. But at the core of everything: value-based selling. Our core curriculum, everything is built off of value-based selling. Even for the CSM — value realization for the CSM is the biggest thing at Vanta. Whether you're an SDR, solutions engineer, AE, account manager — whatever your role, it always is going to start with value-based selling. But then the skills in terms of your actual day-to-day obviously vary a lot. A CSM doesn't need to know how to prospect effectively.
What we've done is get specific not just on role-based enablement but also segment-based enablement. The needs of the upmarket AEs are different from the top three priorities of the downmarket AEs. There's definitely crossover, but the teams have gotten so big and the leaders are adamant about having only the most relevant content put in front of their teams — and I completely agree.
We've also been developing a curriculum that really builds upon itself. We have AEs or SDRs who enter the business brand-new to sales, and then some who have a lot of experience and maybe don't need negotiation 101. So we're creating a curriculum where, okay, maybe this new hire can go automatically to the advanced level of this skill training, whereas another new hire needs to start from scratch. In order to build a curriculum like that, you need a lot of content on deck and the help of some awesome instructional designers and AI.
With that being said, we still collaborate a ton. Today I was in a meeting with our enablement team where the post-sale side was talking about multithreading. And I was like, I want to leverage that framework for AEs. And then the SDR manager was like, SDRs should be learning this content too. So we're very transparent about the priorities of each business we support, and that way we're not reinventing the wheel.
Alex Kracov: And does the curriculum always start from the role — SDR, mid-market, enterprise — and go from there?
Morgan: So this is something I'm very passionate about. It really starts with a set of core competencies. Some of those competencies are the same across go-to-market, and then there are a lot that are very different. I think it's really important — even for a startup — to get aligned between your sales leaders and your people team on what are those core competencies? What are the skills that any AE in any enterprise organization should have? As long as you can get alignment on that, then it's much easier to build out a curriculum. And if someone asks for something outside of the curriculum, that's your opportunity to say, hey, sounds like this might not be a big priority — curious where this is coming from. I do my own discovery there.
Alex Kracov: That's where it helps to be a former seller. You can reverse it on them.
Morgan: Yeah, what outcome are you looking to achieve there? Is there another way we can hit the same outcome with a different skill?
Alex Kracov: And one of the things the enablement team just ran was the CKO. You just did one in Vegas, which sounds fun. Can you take us behind the scenes — what goes into putting on a big CKO like this, and why even do it?
Morgan: Oh my gosh. Well, Alex, as you know, we are a mostly remote organization. We do have offices where certain roles come in a couple of days a week, but the vast majority of our company is remote. So an opportunity to all come together is not only welcome — it's begged for all the time across the team. We're a very social company, we love each other, we really want to spend more time with each other. So obviously the obvious reasons to foster culture and collaboration and empathy across different roles and responsibilities. Even just hearing about what others on the team do, having no idea what their day-to-day looks like — that's big.
I can't take credit — enablement can't take credit for all of the planning that goes into CKO because we have an events team that does an incredible job with the logistics. What enablement does is help shape a lot of the breakout content. When you go to something like a CKO, you can expect some main stage content — get really hyped on the products coming this year, what the year will look like from a vision perspective. But then we've got to get really down into our teams and roles. So I work very closely with our sales leaders and sales managers to come up with that content.
Stevie, our CRO, this year really wanted to focus on team selling as a big pillar theme for CKO. So we took that back to our respective teams and put together content in collaboration with the sales managers. And what's unique about Vanta versus other all-company events I've attended is we involve a lot of the ICs themselves. We have SDRs coming up and showing, here's how I work really well with my AE, here are the LinkedIn videos that have gotten me success. We bring them up to speak firsthand on what's working. Sharing best practices is something we do really well here, and a stage like CKO is a great forum for that.
Alex Kracov: And you say CKO — company kickoff — so that's literally everybody? Engineers, product, everybody?
Morgan: Literally everyone. Engineers, product, we even have channel partners that come. I don't know how many more full-company CKOs we're going to do versus just revenue ones — I think next year might be revenue only. We're getting a little big for that even by Vegas standards. But it was so much fun and amazing.
Alex Kracov: All right, everybody in the world is talking about AI and how it's impacting things. How do you think about using this technology from an enablement perspective? Are you using AI at Vanta to help enablement?
Morgan: Yeah, so the way I personally like to think about AI is: AI is not going to replace human-to-human coaching. I don't think a rep ever wants to be coached by a robot. That's best served from a human — like their manager or a peer. But AI is an excellent way to detect or diagnose gaps to coach on. It's almost like enablement and frontline managers' best friend running analysis in the background.
I'll give you an example. Gong — I promise I'm not being paid by Gong to say this, but it is my favorite tool that I use. Gong obviously not only provides transcripts, but they can even auto-score calls. They can really help detect trends in a rep's sales acumen. You can give it a handful of calls and it'll make that diagnosis for you. Is it 100% accurate? Probably not. You're gonna need to validate its hypothesis, but it's an excellent starting point.
Some other things that we've built recently: we use Dust. It's basically an AI bot where you can build different agents, and it has all of Vanta's universe behind the scenes. We've been able to build Dust bots for things like competitive intel — we call it Compete GPT. So let's say I'm in a deal against OneTrust, they care about privacy, the company's 400 people — what are the top three things I should really lean into? What are the differentiators? Or: hey, I'm in a deal against Drata — what are our strengths in our third-party risk management tool versus theirs? We can get really specific there. We also built one for pre-call research. Gone are the days of searching Google for where's their trust center, what frameworks are they pursuing, who's their ICP — this agent pulls it all in like two minutes.
We actually have folks on staff who are solely dedicated to AI for internal use. I'm not even talking about AI in the Vanta product — I'm talking about how Vantans can use AI to do their jobs better. We have multiple folks on staff full time to help us build these kinds of agents and bots.
Alex Kracov: One interesting thing you said is that sales might be like the last category to get automated because it's so personal. But there's a category that's popped up a lot — AI sales roleplay. Have you used any of those?
Morgan: Yes, we use one of those bots — I think it's called Hyperbound, it's like a cold call simulator. So our SDRs who are brand new, it's really helpful for them to take the edge off, to get comfortable being on the fly, being audible-ready. Taking questions and trying to pivot and answer quickly — really helpful for those scenarios just to get some practice and reps under their belt.
Where I'll stand by this: I can tell, as a user, as a prospect for companies trying to go after me, I can tell what emails are AI-written and which are human. There's a reason why our SDRs — more than 20 of them are going to President's Club this year — the ones doing really well are the ones doing that personal, face-to-face, "hey, I'm a human on LinkedIn, I promise" approach. Humans still want to talk to humans. I think there are certain things a bot can really help with — maybe getting a high-level demo overview or giving you pricing. But at the end of the day, humans still want to be sold to by humans. It's just been evidenced by their success.
Alex Kracov: It's amazing how we can spot it so subconsciously, like email copy. They're probably better emails than I can write, but you can always spot something's fishy.
Morgan: Absolutely. Those bots have a great use case for practice, but I don't know that they'll replace what we're doing as humans. I'm not so worried about that yet — but maybe those are my famous last words.
Alex Kracov: Your job's still safe. All right, maybe my final question — if you were talking to an enablement leader at, say, a 500-person company, what would you tell them to prioritize this year?
Morgan: Hmm. First of all, if you're not on great terms with your rev ops team, send them some cupcakes and get on their good side, because they have been instrumental in helping us make more data-backed decisions. When you're really early on at a company, everything gets surfaced up anecdotally. And sometimes the loudest voices in the room can sound like the biggest problems, but maybe it's just one single loud voice. It's so important to always go back to what the data is telling you. Is this really a top close-loss reason for us, or is this just maybe someone loud who wants it for two people on their team?
Also, the folks on my rev ops team have been instrumental in helping build these AI agents we use to make our reps more efficient. So I'd say a tight relationship with rev ops is a big, big one.
Another one: if you haven't already, purchase a Gong or a Chorus or something similar. I stand by this. Reps love to learn from each other. You do so much more effective by showing them a top performer deliver a talk track versus me delivering a talk track in a training. They want to learn directly from each other, and Gong is the best way to identify those people but also identify those gaps. And they're continuing to make the AI components of their tools more accurate. Those would be my top two suggestions if they're not already doing them.
Alex Kracov: Those are great ones. Well, thank you so much for the time today — this was super fun.
Morgan: Yeah, of course. Thanks for having me.
