Justin Driesse doesn't have an LMS. He doesn't want one. What he does have is a pair of AI agents inside Notion that generated nearly 300 account plans in nine business days—and a sharp philosophy about why most enablement teams are still spending time on the wrong things.
In this episode, Justin joins Alex to break down how he's rebuilding enablement from scratch at Legora and what it looks like when you stop producing content and start compressing the work reps already do.
He shares:
Enjoy the show!
Alex Kracov: So Justin, you spent the last few years enabling AI products — Slack AI at Salesforce, Writer's generative AI platform, and now Legora's legal AI. I'm curious, how did you end up specializing in AI enablement? And was that intentional or did you just follow the opportunities as they came?
Justin Driesse: I think a little bit of both. I think it's probably the latter than the former if I'm going to sequence them. My exposure to AI products started when I was at Slack and I was leading the strategy for all tier one product releases. And so when Denise Dresser came in as the CEO, immediately she was like, we've got to do something big, we've got to pull something forward. And so Slack AI was on the roadmap for a late H1 release. And she just rallied the troops — again, inspirational leader Denise, she's at OpenAI right now — and we all just said, okay, let's plug our nose, let's jump in. And we launched Slack AI way ahead of schedule, but it was one of those things where it was the right product at the right time.
My goodness, the appetite for that product when we launched it was just so massive. It coupled so well with the opportunity. There was Salesforce's company kickoff and Slack had our company kickoff and it was just like, it was the right time to build momentum within our organization and then externally with the market. And so we launched that product. It was really successful upfront. And then, interestingly enough, as I was doing my research for Slack AI, one of the early partners of Slack AI was Writer.
And it was one of those things where I looked through — I believe there were five companies that were going to partner with Slack — they all made sense. And I knew every name except Writer. I didn't even know the name. I was like, Writer, what is that? And so I looked into it and, like we were talking about before the recording started, what they were doing was so interesting and so differentiated. And I loved working at Slack, I mean, talk about cool — I joined Slack after joining another acquisition, and as the head of enablement there, it's Bradford — the best guy in all of enablement. He's recruiting me and he's like, hey, I have this role leading the product strategy for product enablement. And I was like, I just did an acquisition with Twitch and Amazon. I'm not trying to go on that ride again, brother. That was some turbulence. And he's like, okay, if you can turn down the chance to own the strategy for the most iconic product in the history of enterprise SaaS, you're a better man than I. And I was just like, oh, right. Let's do this. It was like the best salesmanship.
But yeah, so spend the time at Slack, but at Writer it was just like, wow, okay. This is a totally different game. They build their own models. They had multiple agent building solutions by the time I departed. And I thought, you know what, this is going to take my career in a totally different direction. So I went all in. My first startup was going to Writer and I couldn't imagine both a better experience of working there and just a more robust education. As part of my interview process — there was such a high bar for talent at Writer — I had to give a mock training on retrieval augmented generation, fine tuning. And I remember looking at the prompt and thinking, I cannot turn this around in 72 hours like I initially said I could. But it all went well.
And you think about what Writer offered me, going from Slack AI, which was a good product but very much a bolt-on feature to an existing feature set, to Writer where you're going to learn about everything in the multiverse that is AI. Just so fortunate to have spent that time there. And again, their co-founders, May and Waseem, just the most generous people in terms of how they treat their employees, how they work with you.
And then now, here at Legora, going from Writer into Legora — I had a bit of skepticism initially towards the industry-specific legal AI thing. But once I met the team and I understood the vision, I was like, this is different again. And so whether it was Slack AI, over to Writer, now to Legora — I think I've had the good fortune of having these opportunities, but then like anything in life, you've got to capitalize on those opportunities.
Alex Kracov: And so this technology is changing so fast. It's hard to keep up with all the different developments in AI, both from the model companies, but then all the different application companies — Slack, Writer, Legora are shipping new products all of the time, trying to keep up with this insatiable demand. What makes selling an AI-native product unique? And then how does that impact your job as the enabler?
Justin Driesse: Yeah, that's a great question. And I think it broke something that needed to be broken. I think a lot of enablement teams fall into the trap of content and producing content. And I had this conversation earlier this week with a good friend of mine — I think that enablement needs to detach itself from the content-making business as quickly as possible. Because you think about what content is, what enablement teams make — e-learnings, one-sheeters. What they're really trying to do is lower the barrier of entry into a complicated concept that people aren't familiar with, but that's kind of like before-times technology.
Now with AI, my biggest learning from the last six months is how labor intensive learning used to be. Like, to learn something, people used to have to drive to a library, use the Dewey decimal system, find an encyclopedia, and think about all the hunting and pecking you used to have to do. Then computers came out — okay, I could do this from the comfort of my home, but you're still largely hunting and pecking. I can go into ChatGPT or Claude right now and say, I want to become an expert on this but I want you to teach it to me like you're an a cappella singer — it's going to do it. Explain this to me like it's an episode of SpongeBob SquarePants — it's going to do it. We live in this age where it's never been easier to learn about things.
And so that's the paradigm shift that enablement has to make. You used to have to build e-learnings and use all these mediums to make concepts simpler for people. And now it's totally rewired the game where I think enablement has to remove themselves from content and just focus on a concept I've come to call "seller empathy," where it's like, look, it's never been harder to be a salesperson. The pace of change is never going to slow down. And disruption is the expectation — I don't think that's ever been the case in any other tech industry, where the expectation is that all of your current solutions will be disrupted by AI repeatedly, all the time.
And so what AI has allowed us to do with salespeople is say, yes, their job is getting harder. But the way that I'm building my team at Legora, our solutions cannot be additive. They have to be distillations of what they do currently, whether that's through agents or automations or whatever it is. We don't have an LMS. I never want to have an LMS. I'm a bit of an enablement tools anarchist, if you will. I've always felt like less is more. It's going to be a cold day when I go and engage on that one — watch, this is going to get clipped and I'm going to have 15 LMS sales people in my DMs.
Alex Kracov: You're going to buy the Dock LMS that we're building one day. No, I'm kidding.
Justin Driesse: We've had tremendous breakthroughs with Notion here. When I came into Legora, there was a huge Notion culture. I'll tell you, the grassroots enablement that existed before I got here was impressive. It was a leading indicator of the care that everyone takes for one another here. What they lacked was that enablement distribution.
Not to go too far on this, but I always look at the role of enablement like the music industry — like the role of a record label. They're not the ones writing the music, they're not in the studio recording it. They are there to make sure that all of their artists are successful. That's kind of how I treat my stakeholders. I think of enablement as the record label. And it's like, listen, I don't want your record to drop at the same time as their record. So I might sequence things and say, hey, can we wait a couple of weeks? Or we're going to launch new messaging — how do we know it's successful? Well, the record label is going to track radio plays, ticket sales, Spotify downloads. So my friends in product marketing say, hey, we have new messaging coming out. And I come to them and say, okay, here's the distribution plan. And here's how we know it's going to be successful. Here's our Gong trackers, all that stuff.
Notice that nothing I've talked about is even adjacent to creating content. It's all about how do you get information into the hands of the field in the most frictionless way possible. And the keystone to all of that is this concept of seller empathy — how do you empathize with someone who's trying their best, trying to stay on top of all this stuff. Most of these people have families, I have a young family myself, and I get how hard it is to have to work through all this stuff right now.
Alex Kracov: So what's an example? I love what you're talking about here — the old world of enablement was static content, LMS systems that no sales rep actually wanted to do. If they had to do it, they'd just click through it and check the box. What does modern enablement look like? What's a real example of how you're still teaching people things — especially in a world of AI where it's changing so fast and legal tech is really complicated and nuanced?
Justin Driesse: Yeah, so we've had two huge breakthroughs at Legora in account planning and demos. And the demo one is interesting because at Writer, I built a program called Demo Domination. Initially it's a mouthful, but it's memorable. It was funny — the first program I ever put in front of May, right, May Habib — the deck was called "Operations Demo Domination: We're Going to Teach the Field How to Dominate Their Demos." And May's like, Justin — she goes, I love that name so much, everything is Demo Domination. And it just became woven into the fabric of the company.
But I've evolved it since coming to Legora, just with the advancements in agents. When I first rolled out Demo Domination — literally a year and a half ago, not even — it was a quarter-over-quarter program. Here's the problem we face, here's how we make that problem smaller and more manageable for salespeople. We need to organize all the demo prep materials that people have. So using Slack's Lists feature — not super widely adopted, but as someone who used to draw a paycheck from Slack, I was super familiar with it — we took all the demo content and put it right in Slack because that's where the team was working. Organized by use case, organized by vertical. And by organizing that, we also taught the team a demo methodology. Between Q3 and Q4, by giving them those assets, we noticed a 33% bump in demo acumen as assessed by their manager. Not me in enablement cooking the books — their manager scored them from Q3 to Q4. It was like a 31% bump in demo acumen quarter over quarter.
That's good enablement work. That's a good program. But think about it — two quarters in the age of AI is a lifetime. And so now, using Notion, we're working on a solution right now where your Notion instance becomes your RAG system. Don't worry about RAG pipelines, don't worry about buying an adjacent solution. You use Notion, that's your RAG. And then the Notion agent — you just tell it which Notion pages to read and what you want to do with that information. You're incentivized to have really good Notion hygiene, and then the agent is just as simple as writing a Notion doc.
Now as we're trying to improve the way that we demo here at Legora — we have examples of what good demos look like, we have archives of the top legal use cases by certain practice areas. So the agent is going and spinning up demo scripts based on who you're talking to. It reads the account plan. Who are you working with in the account? What is their role? What are their interests? Because what's great about legal is — selling to this niche audience of law firms, LLMs know the legal industry really well. They're not lawyers, but the legal industry is not proprietary information. They understand what a partner versus a managing partner versus senior associate is, what drives them, what their motivations are.
So you can get away with a lot — take the account plan, which is all publicly available information. We're using an agent to build our account plans for us. We're doing hours worth of work in just these two agents working in concert together. The before and after is: at Writer, this was a two-quarter, four-to-six-month program that yielded a good result. Now we did this in a couple of weeks just by building these two agents.
Within, I'll call it nine business days of launching account planning, there are close to 300 account plans because the reps caught it — it went viral. Think about what it used to take to enable an entire global sales org on account planning. That's probably another one-to-two-quarter enablement program. Now it's not additive. It's distillation. Nobody in a sales org would look at you and say account planning is a waste of time. It's a time thing — how much time do you have in the day and how do you allocate it? So we take these processes that are critical to running a good sales cycle and we find agents to accelerate the work that people were already doing.
The analogy I like to use is: if I told you that you've got to eat clean, you'd list out all the steps — get in the car, go to the grocery store, buy the food, find recipes, cook, clean. The agents we're building are really like meal delivery services where it's like, all that time you were going to spend doing all that stuff, spend it working out, spend it with your family. How do you find areas where you can compress elite sales execution into an agent and then hand that to your team?
Alex Kracov: Is the workflow that an AE just goes into Notion and starts prompting — hey, I need an account plan for this law firm — and it spits it out? Or is the enablement team sort of looking at calendars and delivering account plans automatically? What does it feel like to be an AE using these tools?
Justin Driesse: So the theme for our kickoff this year was "Yes Chef," right? The idea was, hey, what got us here is not what's going to get us there. The unlock isn't more grit and determination — it's discipline and productivity and focusing on the things that matter. So if you're a rep, you go into Notion, you add the Notion agent — it's five prompts chained together and they all feed on one another. You open the Notion agent and you type in "Yes Chef." And then it reads the title of the account plan and goes — it's all public-facing information that a rep would be researching and compiling into an account plan on their own, but it just goes. The agent has all of the prompts.
And what's more important isn't just what you're telling it to do, but also what you're telling it not to do — because the early beta tests came back with a lot of wheat and chaff. So we had to separate the wheat from the chaff. We were really specific on what we wanted. Now what you get is this very repeatable, robust account plan structure. The prompt is proprietary — I'm not going to share it — but I used Notion to help me write it. It wasn't me sitting there pen and paper scratching it all out. It was me going back and forth with the agent saying, here's what I want to do, I want to include this. And now you have the account planning agent working hand in hand with the demo prep agent, and it's all coming together in one account plan.
Alex Kracov: I totally get how this helps accelerate sales once sellers are already onboarded and working with customers. But how do you think about onboarding and ramping new AEs, especially because legal tech is so complicated? Both my parents are actually lawyers — they do completely different types of law, there's so much nuance. And I assume if an AE gets on a call and starts talking about litigation law to an M&A lawyer, they're like, this doesn't make any sense. So how do you think about teaching an AE about the legal industry? Or are you just hiring AEs who already know law?
Justin Driesse: I think the existing knowledge of legal and legal tech varies person to person. But one thing I'm very clear on as I'm building my team is that onboarding will have an outsized impact on what enablement means for Legora this year. The growth goals we have — if we're doing our job well, ramp is very compressed and that should be the focus of everyone.
I made the conscious decision not to hire one person to focus on onboarding because I was like, that's going to be all of our jobs. It's not going to be like Eric's job where you toss a new concept over the fence to him and let him figure it out. We're all in this. We're going to have skin in the game. And as we own different pieces of the enablement roadmap, everyone's accountable for making sure their piece of the roadmap is accurately represented in onboarding.
Our onboarding program is really sophisticated because it has to be. And that's where we're spending a lot of our calories as an enablement team. Because I think it's always been the case in any sales organization — the richest window for impact on a salesperson is when you onboard them. A lot of times onboarding becomes not-sexy. It's not generally what gets people promoted in enablement. But I think in the era of AI, where we're moving so fast, whatever knowledge gaps people leave their first ramp period with just compound over time. And if you have stale, bad information in your onboarding that you then have to take out of their heads — think about how many things people have to keep up with on a regular basis at these hyperscale AI companies. There's no room for knowledge gaps. There's no room for misinformation.
So to me, onboarding is critical. We have multi-week certification systems and we're very dialed on the metrics we're looking at, what good looks like, and where managers should be leaning in. The way I position our onboarding program to our leaders is like, there's only so much time you can spend with a new hire. The purpose of onboarding is to give you high-fidelity signal on where they're strong and where they're soft, and where you should prioritize your time. That's why as we have these certifications and ramp metrics in place, it's to let leaders know — okay, they're good on A, B, and C, but they really need to work on D. So let me prioritize that in my one-on-ones.
And it's not just how do you make the experience better for sellers — it's also how do you make the experience better for managers? Just this morning, my first hire Jeff and I proposed a program around pipe hygiene. Pipe hygiene is not sexy, but there are ways to positively encourage things that a manager then doesn't have to coach against. Things that we all know people should be doing, but that fall by the wayside when you're trying to move as fast as you are selling an AI. So how does enablement bolster that with a really killer program, so that's one less thing the manager has to worry about?
Alex Kracov: When you're doing those certification programs, is it happening on live calls with prospects that you're listening to in your call recorder and evaluating? Are you doing real role plays? Do you use AI role play? What does a certification program look like at Legora?
Justin Driesse: Throughout my career, I've always seen certification as a bit of a nuanced concept. To me, you're not truly certified until I see that you can do this with a customer. There are two layers to it: field readiness — you know this well enough to get in front of customers — and then what does it look like when the bullets are flying? What does it look like when you're dealing with a customer who clearly doesn't want to be there with you? That's way different than preparing something with your manager where they have four canned questions that every rep tells every other rep about in advance.
So I treat certification as a lever you should only pull so often, and when I do it, I believe in doing it right. It's always a two-layered approach: do you have the ability to do it, and how do you perform with it once you're in front of customers? Because I think too often we fall into the trap of a performative cert — you know, at kickoff, you ask people to come up with a prepared script or a demo, but there's just such a big delta between that and what they do in front of customers.
Back to the concept of seller empathy — my goal is always to make my enablement programs as authentic and organic as possible to what they do out in the field. So I'm a big believer in what I call team certifications, where it's like, hey, we're going to go through a training, and then the manager is going to bring this into their next team call and walk through three or four scenarios that are directly related to the content from the training. And you can tell based on the team's responses whether they're picking up on the different ways we want to approach discovery, or whether they're still falling into old habits. I understand the role of role play and it's never going to go away, but there's a reason it has the stigma it has — it's just not an organic experience for salespeople.
Alex Kracov: And I think you captured it at the beginning too — everyone knows how to game a role play. But when you get on a call with a customer who barely wants to talk to you, all the rules go out the window and you've got to react in real time. That's where real sellers actually thrive.
Justin Driesse: Yeah. I've carried this talk track with me across my last three companies — whenever I teach demo methodology, I say, look, you're going to spend days obsessing over this demo. Meanwhile, you are just another call on their calendar for that day. Especially if you think about your executive decision maker — you don't know what's going on in their world. Maybe their kid got suspended from school. How much do they care about your demo right now?
There's seller empathy, but I also try to teach prospect empathy. You want to use pitches and demos to evangelize the person on the other side. The advice I give people — and I gave this to someone a couple of hours ago — is, you want to wow people. But for you to really buy someone a gift that wows them, you've got to know a lot about them. Discovery. What's their AI acumen? We want to come guns blazing with this incredible AI legal tech, but if you come in way over their head, they're going to be like, oh yeah, cool AI demo. Versus if you can tell them, this is the thing that solves the use case that is keeping you from hitting your growth goals — think about those two totally different conversations they're having going back into their company. Hey, I just did a demo with Manny and guys, he can literally solve the M&A disputes use case. I'm going to set up another call. Versus a spray-and-pray demo showing them everything but the kitchen sink. Meet the prospect where they are, and you're far more likely to get them to promote you internally — which to me is the ultimate goal of that interaction.
Alex Kracov: That's the classic demo mistake. I made it demoing Dock — you just want to show off all your features. Look how cool I am, as opposed to making it about the person you're talking to, understanding their needs, and mapping your solution back to their problem. I still need to get better at that.
Justin Driesse: And that's only human. I give you this advice not because I'm better than you — I'm not on the phone calling customers every day. It's human. You're so bought in on this company and you think this is so cool. But your first principle should always be: how do I meet this person where they're at? The goal of any sales call is to get the next call, but equally important is: how do you get this person promoting your solution internally once they're off the call? Because that is the goal.
Alex Kracov: Well, that's the key to all software, I feel like. Someone buying a piece of software like Dock or Lattice — their job is kind of on the line. At Lattice, they were buying performance management software and it's an HR person. If that rollout went bad, they probably weren't going to have their job anymore. When you're buying a piece of software, you're putting your name on it.
Alex Kracov: All right, switching gears a little bit. How do you think about collaborating across the revenue team? The AEs we've talked about a lot, but how do you think about collaborating with sales leadership and then marketing?
Justin Driesse: Yeah, great question. I think it's two different approaches. When I think about marketing, that leans back into the record label analogy — when it's product marketing or an innovation team or anything like that, the work you do with them is very much like, okay, I want to maximize the ROI for you on everything you're doing with the sales team.
A lot of that comes down to sequencing. You don't want your top two artists releasing a record on the same day. They'll both sell well, but not as well as they could have if you sequenced it. I see myself as the guardian of organizational calories. If we do release things and it's not sequenced well — not here at Legora, but at prior companies — I've seen product marketing messaging released without the proper rollout and implementation to the field. Here's what happens: the field doesn't really understand it, they don't pitch it with confidence, it gets rejected, and then you wind up in this cycle of wasted organizational calories. Why didn't the messaging work? It does work — we just didn't integrate it well.
That's what enablement can do a lot to mitigate. When someone comes to you and says we want to release new messaging, and there are five selling weeks left in the year — maybe we wait. It's not because I don't think your messaging is good. I think this is going to result in additional organizational calories. And then when we do it, why don't we have the CRO do it? Nothing will instill more confidence in the field to use the new messaging than seeing the executive-level version. I've seen that be really successful versus defaulting to a good rep. Getting the CEO or CRO to do it in a way that's really alluring buys a lot of early confidence in the messaging.
When we launched new messaging here at Legora, our CRO delivered it via Loom, and I want to say 94% of the field viewed it within the first 12 hours. Because we found the right moment in their schedule and it was him delivering it, so boom — it took off.
Alex Kracov: It's a great lesson. I was on the other side of that at Lattice — always wanting to do so much new stuff, new campaigns, new things. And you learn the hard way that sellers need to focus on selling and can only digest so much. We definitely fell into that trap so many times.
Justin Driesse: Totally. And that's why you try to be super empathetic with all parties. You've got to lead with empathy. I understand how hard you worked on this and I know how badly you want this to be successful. I promise I'm not resisting this to get in your way. I've just found you a better path — it's over this way. And then you walk them through it, you go hand in hand to the finish line, and they go, okay, I get it. And once they see that you've helped them avoid the landmine, you're their best friend for life.
Alex Kracov: So you just have a weekly meeting with product marketing to get ahead of these things — to know that hey, marketing wants to roll out new messaging or there's a new campaign?
Justin Driesse: Yeah, I'm fortunate to have incredible cross-functional stakeholders here at Legora — product, product marketing, marketing in general. We have an embarrassment of riches in terms of people talent here. We have a weekly meeting — product ops, product marketing, and myself — and we stay well ahead of the pipeline with no surprises. And even simple stuff, we've optimized the process. Early on they were like, Justin, you're enablement, you should post everything. And I'm like, if I post everything, it actually dilutes the signal. It's actually good for them to see the VP of Product popping up in a channel — they know they should pay attention. If there's a marketing thing, our VP of Product Marketing should be the one to post it. Whereas if it's just me, it becomes noise.
Same thing with the CRO delivering the pitch — people notice when he posts. This is him actually doing the pitch. Cool, let me take a look. That's how you get that 90-plus percent view rate in the first day.
I'm also a sucker for structure. It all comes down to being really diligent on your roadmaps and documenting things, making everything readily visible and available. When I come in to run an enablement org, people are sometimes almost quasi-intimidated by the level of documentation, but once they understand — look, there is a roadmap, and there's a program guide for everything we do — initially it's like, wow, this is a lot of slides. But I am here to tell you, Alex: slides save lives. Once people understand the roles and responsibilities that the documentation defines, that's another great way to build trust cross-functionally. When we did our kickoff, I might have spent a few hours building a program guide. Those slides got shown like hundreds of times over the four months we planned kickoff. It's an investment of time, but it's all about that ROI moving forward.
Alex Kracov: Let's talk about that sales kickoff. It just happened like a couple of weeks ago — it was a three-day event in Stockholm, right? Maybe we start with why you even do a sales kickoff. I assume you're taking sellers off the phones. I assume it costs a lot of money to bring everybody together. What's the purpose?
Justin Driesse: Yeah, it's a great question. It's a bit ceremonial in a sense — it represents less than 1% of their calendar year, if you think about it. And when we were in the early innings of planning kickoff, everyone wants to get their thing in front of the sales team. But what I remind people is, this is not the only time you'll have to present to them.
You have to be very clear on a couple of things: what is the strategic objective of this event, and what are the metrics that this event is driving facing forward for the rest of the year? What this event becomes is: here is what we're doing, here's how we're doing it, and here's how we'll know if this is successful. I have in my program guide for kickoff that anything going in front of the field over these three days has to be directly correlated to our strategy to win for this year. It has to be measurable. And then we teach them, give them a hands-on workshop to apply it, certify them on it, and track adoption over the next at least two quarters.
For your cross-functional stakeholders, it's very easy for them to understand, and it makes it easier for them to understand why you're saying no to certain ideas. It's not that I don't value this — it's that for this week, it just doesn't fit the theme. And for this week to work, we really need to be dialed in on what is the most important thing the field needs right now.
Alex Kracov: And what's an example of one of those things where you taught them something and then validated it later?
Justin Driesse: Yeah, so the focus of kickoff — and "Yes Chef" was the theme — was getting really clear on our goals and how we're going to achieve them. And then really dialing in on what elite execution of our customer journey looks like. This is all documented in Notion. Legora is wise beyond its years — the company's only existed for less than two years, but it has the hallmarks of a five, six-year-old company. We have a sales process, we have all this stuff, but we're growing so quickly and we have so many new folks. Let's just get really dialed on what elite execution looks like. Because that's what's going to get us from where we are today to where we want to be at the end of the year.
The first day of kickoff was everyone together in one room — the strategy, the revenue keynote, sessions with our innovation leaders. And everything opened and closed with: here is how we fit into the strategy and here's what you should do after this session to activate this. Everything was forward-facing and actionable.
Day two went role-specific. Okay, everyone's aligned on the strategy. Now, if you're in sales, you're going through four workshops — what parts of the buyer's journey are most critical? Leader-led by our star performers — who had the best years, how do we distill their knowledge? And myself and my team worked with all of them to build true hands-on workshops where it's not one-directional teaching. I gave them a template: 10 minutes of teaching, five minutes of Q&A, then 15 minutes of hands-on group work. Do one topic, rinse, repeat, your hour's over. What are the four points of our customer journey most critical for sales, customer success, and other parts of the company?
And then Friday was certification. We used agents to do this — we took the transcripts from all those workshop sessions and spun up three to four scenarios based on what was covered. The managers would lead their teams through a discussion. All real customer anecdotes that people delivered in the room. What would you do if you ran into this? What would you do if your champion just took a new job? And it was all real conversations. So you go from: here's our strategy, here's how you execute it, and here's a chance to practice and get feedback from your team and your manager on the last day.
Alex Kracov: Legora is scaling insanely fast. How do you think about scaling the enablement program over time? You're in the midst of hyper-scale, and you've felt scale before at Slack and Salesforce. Is it just more of the same or are you adding new programs? How do you make sure the enablement program keeps up with the company growth curve?
Justin Driesse: I'd say the best way to distill this is that enablement needs to work with sales leadership to identify what are the signals within our organization — the insights that correlate most closely with growth and velocity and win rates. When we do this, we win this much more. When we have this many people in the deal, our win rate grows 30%. What are those things, and then anchor programs around them.
And I think what enablement can do now with AI is: one, ingest incomprehensible amounts of data, and two, allow you to generate programming off of those insights. Enablement working with sales leadership to identify the areas where, if we double down, we know that win rates would go up double digits within a single quarter. Build programs that reinforce the best practices and best learnings. And how do you build programs that take away coaching responsibilities in a good way for managers — where it's like, everybody knows the importance of account plans. We're going to build an agent so managers aren't chasing salespeople to write account plans. We're going to build a program that positively reinforces elite pipe hygiene, using agents to identify where you're strong, where you're soft, and then deliver just-in-time enablement to help people raise that level.
Alex Kracov: What do you think about your own goals as an enablement function? Are you just tied to sales goals like close rates, or are there other metrics? How do you communicate your own OKRs to leadership?
Justin Driesse: We have specific goals that I'm going to keep behind closed doors. But I love — I don't know if you're familiar with this couple, the Hormozis, Alex and Layla Hormozi. Alex says — and I have a three-hour train commute every day so I consume a lot of his content — he has this wisdom where the basic idea is: understanding what to focus on is the hard thing, but if you can identify the most important things to focus on, executing on them is actually easy. He has another line: we need to be reminded more than we need to be taught. Just focus on the things that matter.
So I'm a big fan of aligning with my leaders on exactly what good looks like. It can change over time, but we always have a scoreboard and we know what we're focusing on. We're very aligned on that with leadership all the way down.
To more directly answer your question: at the rate we're growing, if you're not obsessing over your onboarding program, you ain't doing it right. Nobody made VP of Enablement by building a killer onboarding program, but new paradigms require new paradigms. If your onboarding program is just okay, think about all the knowledge gaps people come out with. Organizational calories are perpetually at a premium at an AI-native company, and any knowledge gaps that come out of onboarding are exponentially more painful than they were before. So P-zero for me is: as we're hiring all these people, they've got to ramp fast and they've got to ramp right.
And then after that, it's about velocity — how do we ramp people as quickly as possible into their roles? And then how do we increase our deal cycle so that we're winning at a higher clip? We win at this rate when we get in front of the right customer. If we can reduce that sales cycle, we can get in front of more customers, increase that win rate.
Alex Kracov: Maybe one way we can end today's conversation — I'd be curious what advice you have for other people who want to get into enablement. You've had a really successful career across a lot of different companies. What would you give to somebody trying to break in, and once you're in the role, how do you keep that career velocity going?
Justin Driesse: I smirked at that because the first question I ask in every interview I ever conduct is: there's no enablement degree. You literally cannot go to college for this. How did you get here? It's almost like, tell me about it.
Alex Kracov: So true. There's no sales degree really either, I feel like.
Justin Driesse: No, but at the same time — here's a funny anecdote. The first interview I ever had for enablement, I was just doing technology training at a global accounting firm. I get a LinkedIn message from a recruiter at Twitch. When I read the message I'm like, this cannot be Twitch Twitch — and it was. In my first interview with my first manager in enablement, I said, so enablement, I've never heard of this. This must be new. And I remember just the look on his face. He's like, nope, not new. But I got the job somehow.
It finds you, right? But the advice on how to keep up once you're in it — there's an Adam Grant line about strong opinions held loosely. I'll give you a real tangible example.
When I was at Slack, the most success I had was when they launched Slack Canvas. It's actually really good — it's just criminally underutilized. When we launched Slack Canvas, this was my first tier-one product release. Everything was anchored around preparing for Dreamforce — which is the sun and moon of Salesforce, it anchors the entire calendar year. Slack decided to preview a ton of stuff at Dreamforce and then launch coming into Q1. But nobody could have predicted that as they launched Slack Canvas — Benioff was on stage like, this is amazing, we're going to do all this in Slack, it was really buzzy — the Slack sales team was integrating into Salesforce's sales team at the same time. And there were like 16 hours of training just on using their Salesforce instance.
And so Slack Canvas was set to come out that month. I remember going to our head of field enablement and saying, we need a few hours of training to get people enabled on Canvas — what it is, the use cases, all that. And he looked at me and said, Justin, ain't no way. This was my first tier-one product release and I was like, oh my God, this is my moment. I've got to make a splash. And he's like, there are 16 hours of training. We can give you maybe a spot here or there. And I'm just like, this is bad. This is really bad.
But I was like, okay, you've got to do something. Just make a move — there's a coaching tactic in hockey where you just make them make a move. The easiest player to defend is someone who's not moving. So I was like, what if we build the most robust canvas? We'll call it an enablement hub and everything you need to know about Canvas is in a Canvas. That's pretty novel. So I learned everything there was to know about Slack Canvas inside and out and built the first Slack enablement hub.
We launched it and the emoji rate on the launch message was not great. I thought I was heading toward the bread line. But then I went to the product team and asked, is there any way to track adoption of canvases internally? And they gave me access to a dashboard. Within the first month, that Canvas had driven 400% more traffic than the Highspot page they had built.
It went from, my goodness, there's no time with the field, what do we do — to being featured in the company keynote at Dreamforce. What wound up happening was I trained the entire 600-person global enablement org on Canvas, and the entire 600-person org pivoted their whole approach. Slack Canvases became the front door for all enablement at both Slack and Salesforce.
And then the cherry on top — I took paternity leave at Salesforce. My wife and I had a daughter, and I'm sitting there feeding her a bottle, and I put on the Dreamforce keynote. The Chief Product Officer of Slack is going through his keynote and then he goes, "I'm really excited to show you this next feature — this is an enablement hub." And I'm sitting there feeding my two-month-old daughter doing the Leonardo DiCaprio pointing gif in real life. He goes, this has exploded adoption of enablement content inside the company. And a few months later, Denise Dresser did the same thing in her Salesforce company kickoff keynote.
I forget how we ended up here, Alex, but it all came from a moment of, you cannot get time with your field, figure something out — to being featured in a Dreamforce keynote.
Alex Kracov: No, it's such an amazing story because it describes what enablement really is — navigating the politics of getting time with the sales team, fighting through that, staying scrappy. It's a great way to end the conversation. Thank you so much for the time today, Justin.
Justin Driesse: Yeah, likewise. Thank you for having me. Oh, and to actually answer your question about how to get into it: enablement is for you if you're just a little bit too intimidated by the prospect of picking up a phone and calling a customer, but you love being part of a team. Sales teams are a very unique thing — it's a very rewarding, well-paying job, but it's a hard job. And it bonds people in a very unique way.
If you're not the type to go out and actually sell, but if you're an enablement person who becomes a valued member of that team — I mean, you might be the field goal kicker, but a lot of times the game comes down to that last field goal. You're not working directly with customers, but you're so embedded with the team that does. And if, for whatever reason, I had to find a different job, I don't know where else I'd find this type of camaraderie. In our office five days a week, as our people close deals, as our new reps close their first deals, they're going up and hitting the gong. And I'm like, I haven't seen this in seven years.
Alex Kracov: And you can live vicariously through the team. It's so fun. I think of it almost like a coach. I started my career in sales — not for me, I don't love closing deals myself. But it's so fun to be part of the team that's winning.
Justin Driesse: Yeah, and you've got to find the right leaders. I've had the best fortune in my career of just finding incredible leaders. Right now, Max is our CEO — there's only one Max Junestrand in the world, and I'm lucky enough to spend time with him regularly. Whether it's him or Pat Forquer, our CRO — if you find the right people to work for, everything you just said is so much more rewarding. At kickoff last year, within an hour of each other, both Pat and Max came up and from the bottom of their hearts thanked me and the team for kickoff. Like, this is great. Seriously, the feedback is so positive. You're part of the team, but when done well, there is such a genuine gratitude for enablement. It's a labor of love. I see how hard the salespeople work, I see how late they're here some nights. So to see it all come together — it's indescribable.
Alex Kracov: That's awesome. All right, let's end it there. Thank you, Justin.
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Justin Driesse is Director of Sales Enablement at Legora, a hypergrowth legal AI company valued at $1.8B after its Series C. He has built his career enabling AI-native products at some of tech's most innovative companies.
At Salesforce/Slack, he engineered the global enablement strategy for Slack AI's GA launch, generating over $105M in pipeline in Slack's highest-ever pipe gen month.
Prior to that, he led enablement through Twitch's integration with Amazon, and most recently served as Manager of Technical & Product Enablement at Writer, where his "Demo Domination" program drove a 31% quarter-over-quarter increase in demo acumen and his AI-driven programming earned an NPS of 93.
Justin Driesse doesn't have an LMS. He doesn't want one. What he does have is a pair of AI agents inside Notion that generated nearly 300 account plans in nine business days—and a sharp philosophy about why most enablement teams are still spending time on the wrong things.
In this episode, Justin joins Alex to break down how he's rebuilding enablement from scratch at Legora and what it looks like when you stop producing content and start compressing the work reps already do.
He shares:
Enjoy the show!
Justin's Career Journey:
Tools mentioned:
Alex Kracov: So Justin, you spent the last few years enabling AI products — Slack AI at Salesforce, Writer's generative AI platform, and now Legora's legal AI. I'm curious, how did you end up specializing in AI enablement? And was that intentional or did you just follow the opportunities as they came?
Justin Driesse: I think a little bit of both. I think it's probably the latter than the former if I'm going to sequence them. My exposure to AI products started when I was at Slack and I was leading the strategy for all tier one product releases. And so when Denise Dresser came in as the CEO, immediately she was like, we've got to do something big, we've got to pull something forward. And so Slack AI was on the roadmap for a late H1 release. And she just rallied the troops — again, inspirational leader Denise, she's at OpenAI right now — and we all just said, okay, let's plug our nose, let's jump in. And we launched Slack AI way ahead of schedule, but it was one of those things where it was the right product at the right time.
My goodness, the appetite for that product when we launched it was just so massive. It coupled so well with the opportunity. There was Salesforce's company kickoff and Slack had our company kickoff and it was just like, it was the right time to build momentum within our organization and then externally with the market. And so we launched that product. It was really successful upfront. And then, interestingly enough, as I was doing my research for Slack AI, one of the early partners of Slack AI was Writer.
And it was one of those things where I looked through — I believe there were five companies that were going to partner with Slack — they all made sense. And I knew every name except Writer. I didn't even know the name. I was like, Writer, what is that? And so I looked into it and, like we were talking about before the recording started, what they were doing was so interesting and so differentiated. And I loved working at Slack, I mean, talk about cool — I joined Slack after joining another acquisition, and as the head of enablement there, it's Bradford — the best guy in all of enablement. He's recruiting me and he's like, hey, I have this role leading the product strategy for product enablement. And I was like, I just did an acquisition with Twitch and Amazon. I'm not trying to go on that ride again, brother. That was some turbulence. And he's like, okay, if you can turn down the chance to own the strategy for the most iconic product in the history of enterprise SaaS, you're a better man than I. And I was just like, oh, right. Let's do this. It was like the best salesmanship.
But yeah, so spend the time at Slack, but at Writer it was just like, wow, okay. This is a totally different game. They build their own models. They had multiple agent building solutions by the time I departed. And I thought, you know what, this is going to take my career in a totally different direction. So I went all in. My first startup was going to Writer and I couldn't imagine both a better experience of working there and just a more robust education. As part of my interview process — there was such a high bar for talent at Writer — I had to give a mock training on retrieval augmented generation, fine tuning. And I remember looking at the prompt and thinking, I cannot turn this around in 72 hours like I initially said I could. But it all went well.
And you think about what Writer offered me, going from Slack AI, which was a good product but very much a bolt-on feature to an existing feature set, to Writer where you're going to learn about everything in the multiverse that is AI. Just so fortunate to have spent that time there. And again, their co-founders, May and Waseem, just the most generous people in terms of how they treat their employees, how they work with you.
And then now, here at Legora, going from Writer into Legora — I had a bit of skepticism initially towards the industry-specific legal AI thing. But once I met the team and I understood the vision, I was like, this is different again. And so whether it was Slack AI, over to Writer, now to Legora — I think I've had the good fortune of having these opportunities, but then like anything in life, you've got to capitalize on those opportunities.
Alex Kracov: And so this technology is changing so fast. It's hard to keep up with all the different developments in AI, both from the model companies, but then all the different application companies — Slack, Writer, Legora are shipping new products all of the time, trying to keep up with this insatiable demand. What makes selling an AI-native product unique? And then how does that impact your job as the enabler?
Justin Driesse: Yeah, that's a great question. And I think it broke something that needed to be broken. I think a lot of enablement teams fall into the trap of content and producing content. And I had this conversation earlier this week with a good friend of mine — I think that enablement needs to detach itself from the content-making business as quickly as possible. Because you think about what content is, what enablement teams make — e-learnings, one-sheeters. What they're really trying to do is lower the barrier of entry into a complicated concept that people aren't familiar with, but that's kind of like before-times technology.
Now with AI, my biggest learning from the last six months is how labor intensive learning used to be. Like, to learn something, people used to have to drive to a library, use the Dewey decimal system, find an encyclopedia, and think about all the hunting and pecking you used to have to do. Then computers came out — okay, I could do this from the comfort of my home, but you're still largely hunting and pecking. I can go into ChatGPT or Claude right now and say, I want to become an expert on this but I want you to teach it to me like you're an a cappella singer — it's going to do it. Explain this to me like it's an episode of SpongeBob SquarePants — it's going to do it. We live in this age where it's never been easier to learn about things.
And so that's the paradigm shift that enablement has to make. You used to have to build e-learnings and use all these mediums to make concepts simpler for people. And now it's totally rewired the game where I think enablement has to remove themselves from content and just focus on a concept I've come to call "seller empathy," where it's like, look, it's never been harder to be a salesperson. The pace of change is never going to slow down. And disruption is the expectation — I don't think that's ever been the case in any other tech industry, where the expectation is that all of your current solutions will be disrupted by AI repeatedly, all the time.
And so what AI has allowed us to do with salespeople is say, yes, their job is getting harder. But the way that I'm building my team at Legora, our solutions cannot be additive. They have to be distillations of what they do currently, whether that's through agents or automations or whatever it is. We don't have an LMS. I never want to have an LMS. I'm a bit of an enablement tools anarchist, if you will. I've always felt like less is more. It's going to be a cold day when I go and engage on that one — watch, this is going to get clipped and I'm going to have 15 LMS sales people in my DMs.
Alex Kracov: You're going to buy the Dock LMS that we're building one day. No, I'm kidding.
Justin Driesse: We've had tremendous breakthroughs with Notion here. When I came into Legora, there was a huge Notion culture. I'll tell you, the grassroots enablement that existed before I got here was impressive. It was a leading indicator of the care that everyone takes for one another here. What they lacked was that enablement distribution.
Not to go too far on this, but I always look at the role of enablement like the music industry — like the role of a record label. They're not the ones writing the music, they're not in the studio recording it. They are there to make sure that all of their artists are successful. That's kind of how I treat my stakeholders. I think of enablement as the record label. And it's like, listen, I don't want your record to drop at the same time as their record. So I might sequence things and say, hey, can we wait a couple of weeks? Or we're going to launch new messaging — how do we know it's successful? Well, the record label is going to track radio plays, ticket sales, Spotify downloads. So my friends in product marketing say, hey, we have new messaging coming out. And I come to them and say, okay, here's the distribution plan. And here's how we know it's going to be successful. Here's our Gong trackers, all that stuff.
Notice that nothing I've talked about is even adjacent to creating content. It's all about how do you get information into the hands of the field in the most frictionless way possible. And the keystone to all of that is this concept of seller empathy — how do you empathize with someone who's trying their best, trying to stay on top of all this stuff. Most of these people have families, I have a young family myself, and I get how hard it is to have to work through all this stuff right now.
Alex Kracov: So what's an example? I love what you're talking about here — the old world of enablement was static content, LMS systems that no sales rep actually wanted to do. If they had to do it, they'd just click through it and check the box. What does modern enablement look like? What's a real example of how you're still teaching people things — especially in a world of AI where it's changing so fast and legal tech is really complicated and nuanced?
Justin Driesse: Yeah, so we've had two huge breakthroughs at Legora in account planning and demos. And the demo one is interesting because at Writer, I built a program called Demo Domination. Initially it's a mouthful, but it's memorable. It was funny — the first program I ever put in front of May, right, May Habib — the deck was called "Operations Demo Domination: We're Going to Teach the Field How to Dominate Their Demos." And May's like, Justin — she goes, I love that name so much, everything is Demo Domination. And it just became woven into the fabric of the company.
But I've evolved it since coming to Legora, just with the advancements in agents. When I first rolled out Demo Domination — literally a year and a half ago, not even — it was a quarter-over-quarter program. Here's the problem we face, here's how we make that problem smaller and more manageable for salespeople. We need to organize all the demo prep materials that people have. So using Slack's Lists feature — not super widely adopted, but as someone who used to draw a paycheck from Slack, I was super familiar with it — we took all the demo content and put it right in Slack because that's where the team was working. Organized by use case, organized by vertical. And by organizing that, we also taught the team a demo methodology. Between Q3 and Q4, by giving them those assets, we noticed a 33% bump in demo acumen as assessed by their manager. Not me in enablement cooking the books — their manager scored them from Q3 to Q4. It was like a 31% bump in demo acumen quarter over quarter.
That's good enablement work. That's a good program. But think about it — two quarters in the age of AI is a lifetime. And so now, using Notion, we're working on a solution right now where your Notion instance becomes your RAG system. Don't worry about RAG pipelines, don't worry about buying an adjacent solution. You use Notion, that's your RAG. And then the Notion agent — you just tell it which Notion pages to read and what you want to do with that information. You're incentivized to have really good Notion hygiene, and then the agent is just as simple as writing a Notion doc.
Now as we're trying to improve the way that we demo here at Legora — we have examples of what good demos look like, we have archives of the top legal use cases by certain practice areas. So the agent is going and spinning up demo scripts based on who you're talking to. It reads the account plan. Who are you working with in the account? What is their role? What are their interests? Because what's great about legal is — selling to this niche audience of law firms, LLMs know the legal industry really well. They're not lawyers, but the legal industry is not proprietary information. They understand what a partner versus a managing partner versus senior associate is, what drives them, what their motivations are.
So you can get away with a lot — take the account plan, which is all publicly available information. We're using an agent to build our account plans for us. We're doing hours worth of work in just these two agents working in concert together. The before and after is: at Writer, this was a two-quarter, four-to-six-month program that yielded a good result. Now we did this in a couple of weeks just by building these two agents.
Within, I'll call it nine business days of launching account planning, there are close to 300 account plans because the reps caught it — it went viral. Think about what it used to take to enable an entire global sales org on account planning. That's probably another one-to-two-quarter enablement program. Now it's not additive. It's distillation. Nobody in a sales org would look at you and say account planning is a waste of time. It's a time thing — how much time do you have in the day and how do you allocate it? So we take these processes that are critical to running a good sales cycle and we find agents to accelerate the work that people were already doing.
The analogy I like to use is: if I told you that you've got to eat clean, you'd list out all the steps — get in the car, go to the grocery store, buy the food, find recipes, cook, clean. The agents we're building are really like meal delivery services where it's like, all that time you were going to spend doing all that stuff, spend it working out, spend it with your family. How do you find areas where you can compress elite sales execution into an agent and then hand that to your team?
Alex Kracov: Is the workflow that an AE just goes into Notion and starts prompting — hey, I need an account plan for this law firm — and it spits it out? Or is the enablement team sort of looking at calendars and delivering account plans automatically? What does it feel like to be an AE using these tools?
Justin Driesse: So the theme for our kickoff this year was "Yes Chef," right? The idea was, hey, what got us here is not what's going to get us there. The unlock isn't more grit and determination — it's discipline and productivity and focusing on the things that matter. So if you're a rep, you go into Notion, you add the Notion agent — it's five prompts chained together and they all feed on one another. You open the Notion agent and you type in "Yes Chef." And then it reads the title of the account plan and goes — it's all public-facing information that a rep would be researching and compiling into an account plan on their own, but it just goes. The agent has all of the prompts.
And what's more important isn't just what you're telling it to do, but also what you're telling it not to do — because the early beta tests came back with a lot of wheat and chaff. So we had to separate the wheat from the chaff. We were really specific on what we wanted. Now what you get is this very repeatable, robust account plan structure. The prompt is proprietary — I'm not going to share it — but I used Notion to help me write it. It wasn't me sitting there pen and paper scratching it all out. It was me going back and forth with the agent saying, here's what I want to do, I want to include this. And now you have the account planning agent working hand in hand with the demo prep agent, and it's all coming together in one account plan.
Alex Kracov: I totally get how this helps accelerate sales once sellers are already onboarded and working with customers. But how do you think about onboarding and ramping new AEs, especially because legal tech is so complicated? Both my parents are actually lawyers — they do completely different types of law, there's so much nuance. And I assume if an AE gets on a call and starts talking about litigation law to an M&A lawyer, they're like, this doesn't make any sense. So how do you think about teaching an AE about the legal industry? Or are you just hiring AEs who already know law?
Justin Driesse: I think the existing knowledge of legal and legal tech varies person to person. But one thing I'm very clear on as I'm building my team is that onboarding will have an outsized impact on what enablement means for Legora this year. The growth goals we have — if we're doing our job well, ramp is very compressed and that should be the focus of everyone.
I made the conscious decision not to hire one person to focus on onboarding because I was like, that's going to be all of our jobs. It's not going to be like Eric's job where you toss a new concept over the fence to him and let him figure it out. We're all in this. We're going to have skin in the game. And as we own different pieces of the enablement roadmap, everyone's accountable for making sure their piece of the roadmap is accurately represented in onboarding.
Our onboarding program is really sophisticated because it has to be. And that's where we're spending a lot of our calories as an enablement team. Because I think it's always been the case in any sales organization — the richest window for impact on a salesperson is when you onboard them. A lot of times onboarding becomes not-sexy. It's not generally what gets people promoted in enablement. But I think in the era of AI, where we're moving so fast, whatever knowledge gaps people leave their first ramp period with just compound over time. And if you have stale, bad information in your onboarding that you then have to take out of their heads — think about how many things people have to keep up with on a regular basis at these hyperscale AI companies. There's no room for knowledge gaps. There's no room for misinformation.
So to me, onboarding is critical. We have multi-week certification systems and we're very dialed on the metrics we're looking at, what good looks like, and where managers should be leaning in. The way I position our onboarding program to our leaders is like, there's only so much time you can spend with a new hire. The purpose of onboarding is to give you high-fidelity signal on where they're strong and where they're soft, and where you should prioritize your time. That's why as we have these certifications and ramp metrics in place, it's to let leaders know — okay, they're good on A, B, and C, but they really need to work on D. So let me prioritize that in my one-on-ones.
And it's not just how do you make the experience better for sellers — it's also how do you make the experience better for managers? Just this morning, my first hire Jeff and I proposed a program around pipe hygiene. Pipe hygiene is not sexy, but there are ways to positively encourage things that a manager then doesn't have to coach against. Things that we all know people should be doing, but that fall by the wayside when you're trying to move as fast as you are selling an AI. So how does enablement bolster that with a really killer program, so that's one less thing the manager has to worry about?
Alex Kracov: When you're doing those certification programs, is it happening on live calls with prospects that you're listening to in your call recorder and evaluating? Are you doing real role plays? Do you use AI role play? What does a certification program look like at Legora?
Justin Driesse: Throughout my career, I've always seen certification as a bit of a nuanced concept. To me, you're not truly certified until I see that you can do this with a customer. There are two layers to it: field readiness — you know this well enough to get in front of customers — and then what does it look like when the bullets are flying? What does it look like when you're dealing with a customer who clearly doesn't want to be there with you? That's way different than preparing something with your manager where they have four canned questions that every rep tells every other rep about in advance.
So I treat certification as a lever you should only pull so often, and when I do it, I believe in doing it right. It's always a two-layered approach: do you have the ability to do it, and how do you perform with it once you're in front of customers? Because I think too often we fall into the trap of a performative cert — you know, at kickoff, you ask people to come up with a prepared script or a demo, but there's just such a big delta between that and what they do in front of customers.
Back to the concept of seller empathy — my goal is always to make my enablement programs as authentic and organic as possible to what they do out in the field. So I'm a big believer in what I call team certifications, where it's like, hey, we're going to go through a training, and then the manager is going to bring this into their next team call and walk through three or four scenarios that are directly related to the content from the training. And you can tell based on the team's responses whether they're picking up on the different ways we want to approach discovery, or whether they're still falling into old habits. I understand the role of role play and it's never going to go away, but there's a reason it has the stigma it has — it's just not an organic experience for salespeople.
Alex Kracov: And I think you captured it at the beginning too — everyone knows how to game a role play. But when you get on a call with a customer who barely wants to talk to you, all the rules go out the window and you've got to react in real time. That's where real sellers actually thrive.
Justin Driesse: Yeah. I've carried this talk track with me across my last three companies — whenever I teach demo methodology, I say, look, you're going to spend days obsessing over this demo. Meanwhile, you are just another call on their calendar for that day. Especially if you think about your executive decision maker — you don't know what's going on in their world. Maybe their kid got suspended from school. How much do they care about your demo right now?
There's seller empathy, but I also try to teach prospect empathy. You want to use pitches and demos to evangelize the person on the other side. The advice I give people — and I gave this to someone a couple of hours ago — is, you want to wow people. But for you to really buy someone a gift that wows them, you've got to know a lot about them. Discovery. What's their AI acumen? We want to come guns blazing with this incredible AI legal tech, but if you come in way over their head, they're going to be like, oh yeah, cool AI demo. Versus if you can tell them, this is the thing that solves the use case that is keeping you from hitting your growth goals — think about those two totally different conversations they're having going back into their company. Hey, I just did a demo with Manny and guys, he can literally solve the M&A disputes use case. I'm going to set up another call. Versus a spray-and-pray demo showing them everything but the kitchen sink. Meet the prospect where they are, and you're far more likely to get them to promote you internally — which to me is the ultimate goal of that interaction.
Alex Kracov: That's the classic demo mistake. I made it demoing Dock — you just want to show off all your features. Look how cool I am, as opposed to making it about the person you're talking to, understanding their needs, and mapping your solution back to their problem. I still need to get better at that.
Justin Driesse: And that's only human. I give you this advice not because I'm better than you — I'm not on the phone calling customers every day. It's human. You're so bought in on this company and you think this is so cool. But your first principle should always be: how do I meet this person where they're at? The goal of any sales call is to get the next call, but equally important is: how do you get this person promoting your solution internally once they're off the call? Because that is the goal.
Alex Kracov: Well, that's the key to all software, I feel like. Someone buying a piece of software like Dock or Lattice — their job is kind of on the line. At Lattice, they were buying performance management software and it's an HR person. If that rollout went bad, they probably weren't going to have their job anymore. When you're buying a piece of software, you're putting your name on it.
Alex Kracov: All right, switching gears a little bit. How do you think about collaborating across the revenue team? The AEs we've talked about a lot, but how do you think about collaborating with sales leadership and then marketing?
Justin Driesse: Yeah, great question. I think it's two different approaches. When I think about marketing, that leans back into the record label analogy — when it's product marketing or an innovation team or anything like that, the work you do with them is very much like, okay, I want to maximize the ROI for you on everything you're doing with the sales team.
A lot of that comes down to sequencing. You don't want your top two artists releasing a record on the same day. They'll both sell well, but not as well as they could have if you sequenced it. I see myself as the guardian of organizational calories. If we do release things and it's not sequenced well — not here at Legora, but at prior companies — I've seen product marketing messaging released without the proper rollout and implementation to the field. Here's what happens: the field doesn't really understand it, they don't pitch it with confidence, it gets rejected, and then you wind up in this cycle of wasted organizational calories. Why didn't the messaging work? It does work — we just didn't integrate it well.
That's what enablement can do a lot to mitigate. When someone comes to you and says we want to release new messaging, and there are five selling weeks left in the year — maybe we wait. It's not because I don't think your messaging is good. I think this is going to result in additional organizational calories. And then when we do it, why don't we have the CRO do it? Nothing will instill more confidence in the field to use the new messaging than seeing the executive-level version. I've seen that be really successful versus defaulting to a good rep. Getting the CEO or CRO to do it in a way that's really alluring buys a lot of early confidence in the messaging.
When we launched new messaging here at Legora, our CRO delivered it via Loom, and I want to say 94% of the field viewed it within the first 12 hours. Because we found the right moment in their schedule and it was him delivering it, so boom — it took off.
Alex Kracov: It's a great lesson. I was on the other side of that at Lattice — always wanting to do so much new stuff, new campaigns, new things. And you learn the hard way that sellers need to focus on selling and can only digest so much. We definitely fell into that trap so many times.
Justin Driesse: Totally. And that's why you try to be super empathetic with all parties. You've got to lead with empathy. I understand how hard you worked on this and I know how badly you want this to be successful. I promise I'm not resisting this to get in your way. I've just found you a better path — it's over this way. And then you walk them through it, you go hand in hand to the finish line, and they go, okay, I get it. And once they see that you've helped them avoid the landmine, you're their best friend for life.
Alex Kracov: So you just have a weekly meeting with product marketing to get ahead of these things — to know that hey, marketing wants to roll out new messaging or there's a new campaign?
Justin Driesse: Yeah, I'm fortunate to have incredible cross-functional stakeholders here at Legora — product, product marketing, marketing in general. We have an embarrassment of riches in terms of people talent here. We have a weekly meeting — product ops, product marketing, and myself — and we stay well ahead of the pipeline with no surprises. And even simple stuff, we've optimized the process. Early on they were like, Justin, you're enablement, you should post everything. And I'm like, if I post everything, it actually dilutes the signal. It's actually good for them to see the VP of Product popping up in a channel — they know they should pay attention. If there's a marketing thing, our VP of Product Marketing should be the one to post it. Whereas if it's just me, it becomes noise.
Same thing with the CRO delivering the pitch — people notice when he posts. This is him actually doing the pitch. Cool, let me take a look. That's how you get that 90-plus percent view rate in the first day.
I'm also a sucker for structure. It all comes down to being really diligent on your roadmaps and documenting things, making everything readily visible and available. When I come in to run an enablement org, people are sometimes almost quasi-intimidated by the level of documentation, but once they understand — look, there is a roadmap, and there's a program guide for everything we do — initially it's like, wow, this is a lot of slides. But I am here to tell you, Alex: slides save lives. Once people understand the roles and responsibilities that the documentation defines, that's another great way to build trust cross-functionally. When we did our kickoff, I might have spent a few hours building a program guide. Those slides got shown like hundreds of times over the four months we planned kickoff. It's an investment of time, but it's all about that ROI moving forward.
Alex Kracov: Let's talk about that sales kickoff. It just happened like a couple of weeks ago — it was a three-day event in Stockholm, right? Maybe we start with why you even do a sales kickoff. I assume you're taking sellers off the phones. I assume it costs a lot of money to bring everybody together. What's the purpose?
Justin Driesse: Yeah, it's a great question. It's a bit ceremonial in a sense — it represents less than 1% of their calendar year, if you think about it. And when we were in the early innings of planning kickoff, everyone wants to get their thing in front of the sales team. But what I remind people is, this is not the only time you'll have to present to them.
You have to be very clear on a couple of things: what is the strategic objective of this event, and what are the metrics that this event is driving facing forward for the rest of the year? What this event becomes is: here is what we're doing, here's how we're doing it, and here's how we'll know if this is successful. I have in my program guide for kickoff that anything going in front of the field over these three days has to be directly correlated to our strategy to win for this year. It has to be measurable. And then we teach them, give them a hands-on workshop to apply it, certify them on it, and track adoption over the next at least two quarters.
For your cross-functional stakeholders, it's very easy for them to understand, and it makes it easier for them to understand why you're saying no to certain ideas. It's not that I don't value this — it's that for this week, it just doesn't fit the theme. And for this week to work, we really need to be dialed in on what is the most important thing the field needs right now.
Alex Kracov: And what's an example of one of those things where you taught them something and then validated it later?
Justin Driesse: Yeah, so the focus of kickoff — and "Yes Chef" was the theme — was getting really clear on our goals and how we're going to achieve them. And then really dialing in on what elite execution of our customer journey looks like. This is all documented in Notion. Legora is wise beyond its years — the company's only existed for less than two years, but it has the hallmarks of a five, six-year-old company. We have a sales process, we have all this stuff, but we're growing so quickly and we have so many new folks. Let's just get really dialed on what elite execution looks like. Because that's what's going to get us from where we are today to where we want to be at the end of the year.
The first day of kickoff was everyone together in one room — the strategy, the revenue keynote, sessions with our innovation leaders. And everything opened and closed with: here is how we fit into the strategy and here's what you should do after this session to activate this. Everything was forward-facing and actionable.
Day two went role-specific. Okay, everyone's aligned on the strategy. Now, if you're in sales, you're going through four workshops — what parts of the buyer's journey are most critical? Leader-led by our star performers — who had the best years, how do we distill their knowledge? And myself and my team worked with all of them to build true hands-on workshops where it's not one-directional teaching. I gave them a template: 10 minutes of teaching, five minutes of Q&A, then 15 minutes of hands-on group work. Do one topic, rinse, repeat, your hour's over. What are the four points of our customer journey most critical for sales, customer success, and other parts of the company?
And then Friday was certification. We used agents to do this — we took the transcripts from all those workshop sessions and spun up three to four scenarios based on what was covered. The managers would lead their teams through a discussion. All real customer anecdotes that people delivered in the room. What would you do if you ran into this? What would you do if your champion just took a new job? And it was all real conversations. So you go from: here's our strategy, here's how you execute it, and here's a chance to practice and get feedback from your team and your manager on the last day.
Alex Kracov: Legora is scaling insanely fast. How do you think about scaling the enablement program over time? You're in the midst of hyper-scale, and you've felt scale before at Slack and Salesforce. Is it just more of the same or are you adding new programs? How do you make sure the enablement program keeps up with the company growth curve?
Justin Driesse: I'd say the best way to distill this is that enablement needs to work with sales leadership to identify what are the signals within our organization — the insights that correlate most closely with growth and velocity and win rates. When we do this, we win this much more. When we have this many people in the deal, our win rate grows 30%. What are those things, and then anchor programs around them.
And I think what enablement can do now with AI is: one, ingest incomprehensible amounts of data, and two, allow you to generate programming off of those insights. Enablement working with sales leadership to identify the areas where, if we double down, we know that win rates would go up double digits within a single quarter. Build programs that reinforce the best practices and best learnings. And how do you build programs that take away coaching responsibilities in a good way for managers — where it's like, everybody knows the importance of account plans. We're going to build an agent so managers aren't chasing salespeople to write account plans. We're going to build a program that positively reinforces elite pipe hygiene, using agents to identify where you're strong, where you're soft, and then deliver just-in-time enablement to help people raise that level.
Alex Kracov: What do you think about your own goals as an enablement function? Are you just tied to sales goals like close rates, or are there other metrics? How do you communicate your own OKRs to leadership?
Justin Driesse: We have specific goals that I'm going to keep behind closed doors. But I love — I don't know if you're familiar with this couple, the Hormozis, Alex and Layla Hormozi. Alex says — and I have a three-hour train commute every day so I consume a lot of his content — he has this wisdom where the basic idea is: understanding what to focus on is the hard thing, but if you can identify the most important things to focus on, executing on them is actually easy. He has another line: we need to be reminded more than we need to be taught. Just focus on the things that matter.
So I'm a big fan of aligning with my leaders on exactly what good looks like. It can change over time, but we always have a scoreboard and we know what we're focusing on. We're very aligned on that with leadership all the way down.
To more directly answer your question: at the rate we're growing, if you're not obsessing over your onboarding program, you ain't doing it right. Nobody made VP of Enablement by building a killer onboarding program, but new paradigms require new paradigms. If your onboarding program is just okay, think about all the knowledge gaps people come out with. Organizational calories are perpetually at a premium at an AI-native company, and any knowledge gaps that come out of onboarding are exponentially more painful than they were before. So P-zero for me is: as we're hiring all these people, they've got to ramp fast and they've got to ramp right.
And then after that, it's about velocity — how do we ramp people as quickly as possible into their roles? And then how do we increase our deal cycle so that we're winning at a higher clip? We win at this rate when we get in front of the right customer. If we can reduce that sales cycle, we can get in front of more customers, increase that win rate.
Alex Kracov: Maybe one way we can end today's conversation — I'd be curious what advice you have for other people who want to get into enablement. You've had a really successful career across a lot of different companies. What would you give to somebody trying to break in, and once you're in the role, how do you keep that career velocity going?
Justin Driesse: I smirked at that because the first question I ask in every interview I ever conduct is: there's no enablement degree. You literally cannot go to college for this. How did you get here? It's almost like, tell me about it.
Alex Kracov: So true. There's no sales degree really either, I feel like.
Justin Driesse: No, but at the same time — here's a funny anecdote. The first interview I ever had for enablement, I was just doing technology training at a global accounting firm. I get a LinkedIn message from a recruiter at Twitch. When I read the message I'm like, this cannot be Twitch Twitch — and it was. In my first interview with my first manager in enablement, I said, so enablement, I've never heard of this. This must be new. And I remember just the look on his face. He's like, nope, not new. But I got the job somehow.
It finds you, right? But the advice on how to keep up once you're in it — there's an Adam Grant line about strong opinions held loosely. I'll give you a real tangible example.
When I was at Slack, the most success I had was when they launched Slack Canvas. It's actually really good — it's just criminally underutilized. When we launched Slack Canvas, this was my first tier-one product release. Everything was anchored around preparing for Dreamforce — which is the sun and moon of Salesforce, it anchors the entire calendar year. Slack decided to preview a ton of stuff at Dreamforce and then launch coming into Q1. But nobody could have predicted that as they launched Slack Canvas — Benioff was on stage like, this is amazing, we're going to do all this in Slack, it was really buzzy — the Slack sales team was integrating into Salesforce's sales team at the same time. And there were like 16 hours of training just on using their Salesforce instance.
And so Slack Canvas was set to come out that month. I remember going to our head of field enablement and saying, we need a few hours of training to get people enabled on Canvas — what it is, the use cases, all that. And he looked at me and said, Justin, ain't no way. This was my first tier-one product release and I was like, oh my God, this is my moment. I've got to make a splash. And he's like, there are 16 hours of training. We can give you maybe a spot here or there. And I'm just like, this is bad. This is really bad.
But I was like, okay, you've got to do something. Just make a move — there's a coaching tactic in hockey where you just make them make a move. The easiest player to defend is someone who's not moving. So I was like, what if we build the most robust canvas? We'll call it an enablement hub and everything you need to know about Canvas is in a Canvas. That's pretty novel. So I learned everything there was to know about Slack Canvas inside and out and built the first Slack enablement hub.
We launched it and the emoji rate on the launch message was not great. I thought I was heading toward the bread line. But then I went to the product team and asked, is there any way to track adoption of canvases internally? And they gave me access to a dashboard. Within the first month, that Canvas had driven 400% more traffic than the Highspot page they had built.
It went from, my goodness, there's no time with the field, what do we do — to being featured in the company keynote at Dreamforce. What wound up happening was I trained the entire 600-person global enablement org on Canvas, and the entire 600-person org pivoted their whole approach. Slack Canvases became the front door for all enablement at both Slack and Salesforce.
And then the cherry on top — I took paternity leave at Salesforce. My wife and I had a daughter, and I'm sitting there feeding her a bottle, and I put on the Dreamforce keynote. The Chief Product Officer of Slack is going through his keynote and then he goes, "I'm really excited to show you this next feature — this is an enablement hub." And I'm sitting there feeding my two-month-old daughter doing the Leonardo DiCaprio pointing gif in real life. He goes, this has exploded adoption of enablement content inside the company. And a few months later, Denise Dresser did the same thing in her Salesforce company kickoff keynote.
I forget how we ended up here, Alex, but it all came from a moment of, you cannot get time with your field, figure something out — to being featured in a Dreamforce keynote.
Alex Kracov: No, it's such an amazing story because it describes what enablement really is — navigating the politics of getting time with the sales team, fighting through that, staying scrappy. It's a great way to end the conversation. Thank you so much for the time today, Justin.
Justin Driesse: Yeah, likewise. Thank you for having me. Oh, and to actually answer your question about how to get into it: enablement is for you if you're just a little bit too intimidated by the prospect of picking up a phone and calling a customer, but you love being part of a team. Sales teams are a very unique thing — it's a very rewarding, well-paying job, but it's a hard job. And it bonds people in a very unique way.
If you're not the type to go out and actually sell, but if you're an enablement person who becomes a valued member of that team — I mean, you might be the field goal kicker, but a lot of times the game comes down to that last field goal. You're not working directly with customers, but you're so embedded with the team that does. And if, for whatever reason, I had to find a different job, I don't know where else I'd find this type of camaraderie. In our office five days a week, as our people close deals, as our new reps close their first deals, they're going up and hitting the gong. And I'm like, I haven't seen this in seven years.
Alex Kracov: And you can live vicariously through the team. It's so fun. I think of it almost like a coach. I started my career in sales — not for me, I don't love closing deals myself. But it's so fun to be part of the team that's winning.
Justin Driesse: Yeah, and you've got to find the right leaders. I've had the best fortune in my career of just finding incredible leaders. Right now, Max is our CEO — there's only one Max Junestrand in the world, and I'm lucky enough to spend time with him regularly. Whether it's him or Pat Forquer, our CRO — if you find the right people to work for, everything you just said is so much more rewarding. At kickoff last year, within an hour of each other, both Pat and Max came up and from the bottom of their hearts thanked me and the team for kickoff. Like, this is great. Seriously, the feedback is so positive. You're part of the team, but when done well, there is such a genuine gratitude for enablement. It's a labor of love. I see how hard the salespeople work, I see how late they're here some nights. So to see it all come together — it's indescribable.
Alex Kracov: That's awesome. All right, let's end it there. Thank you, Justin.
