How Justin Driesse uses AI agents to compress months of enablement into days

TABLE OF CONTENTs

TABLE OF CONTENT

Inside Legora's playbook for agent-powered account planning, demo prep, and seller empathy

Justin Driesse doesn't have an LMS. He doesn't want one. ("I'm a bit of an enablement tools anarchist," he says.)

What he does have: a pair of AI agents inside Notion that generated nearly 300 account plans in nine business days.

As Director of Sales Enablement at Legora—the legal AI platform valued at $1.8 billion after its Series C—Justin has spent the last two years enabling some of the fastest-moving AI products in enterprise software.

Before Legora, he led product enablement for Slack AI at Salesforce (where his work drove $105M+ in post-launch pipeline) and ran technical enablement at Writer during its hypergrowth phase.

Three AI companies in two years. The man likes chaos.

But he's learned how to tame it. At Legora, that means agent-powered account planning, demo prep scripts that build themselves from live account data, and an enablement philosophy built around compressing work reps already do—not adding to their plate.

The common thread isn't just "use more AI"—it's a fundamental rethinking of what enablement teams should spend their time on.

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Top takeaways:

Get out of the content business. AI has made content creation frictionless. Enablement's job is now distribution, sequencing, and seller empathy, not producing e-learning and one-sheeters.
Use your existing tools as AI infrastructure. Legora runs its account planning and demo prep agents entirely inside Notion—no separate AI stack required.
Give reps AI tools that remove friction, not add tasks. Legora's account planning agent went viral—nearly 300 plans in 9 business days—because it compressed work reps already valued but couldn't prioritize.
Onboarding is the top priority at AI-native companies. Knowledge gaps compound exponentially when the product evolves weekly. There's no room for stale information in ramp programs.
Leaders, not enablement, should deliver key messages. When Legora's CRO delivered new messaging via Loom, 94% of the field watched it within 12 hours.
Certify in the field, not in a fishbowl. Real certification means observing performance with actual customers, not scoring rehearsed role plays everyone has gamed in advance.

Enablement needs to get out of the content business

Justin's most provocative take is that enablement teams need to stop making content.

His logic: the entire premise of enablement content—e-learnings, one-sheeters, training decks—was built for an era when learning was labor-intensive. You had to package complex concepts into digestible formats because there was no other way to lower the barrier to entry.

That era is over. "I can go into ChatGPT or Claude right now and say, I want to become an expert on this, but teach it to me like you're an a cappella singer—it's going to do it," Justin says. "We live in this age where it's never been easier to learn about things."

So what replaces content? A concept he calls "seller empathy"—a relentless focus on understanding what it actually feels like to be a salesperson right now and removing friction from their day.

"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."

Justin says every learning solution has to be a distillation of what reps already do, not something that adds to it. That’s why he doesn’t use an LMS.

Instead, he builds agents and automations that compress existing workflows—account planning, demo prep, pipeline hygiene—into something that takes minutes instead of hours.

The analogy he uses: telling a salesperson to do better account planning is like telling someone to eat clean—they know they should, but there's a whole chain of logistics standing in the way. The agents his team builds are meal delivery services. Skip the grocery run. Spend that time selling.

Build AI agents that compress work reps already do

The most concrete example of this philosophy in action is what happened when Legora launched its account planning agent.

Legora already had a strong Notion culture—"the grassroots enablement that existed before I got here was impressive," Justin says. So rather than buying a separate tool, his team turned Notion into the RAG system.

A rep opens a page, types "Yes Chef" (the team's kickoff theme), and five chained prompts do the rest—reading account plan templates and use case archives, pulling public firm information, and producing a structured plan mapped to specific contacts and roles.

"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."

A second agent handles demo prep, reading the account plan, and generating a tailored demo script mapped to specific personas.

Early beta tests took a few rounds of feedback from reps, but once the team got specific about constraints, the output became something reps actually trusted—and adopted fast.

Within 9 business days of launch, reps had generated 300 account plans. That's the kind of adoption that used to take a full quarter of enablement programming just to kick off.

Onboarding is the highest-leverage bet at AI-native companies

Justin is blunt about where enablement teams should be spending most of their energy: onboarding.

Not because it's glamorous—"nobody made VP of Enablement by building a killer onboarding program,” says Justin—but because the math is unforgiving at AI companies.

When products change weekly and entire categories are disrupted between quarters, any knowledge gaps that emerge from onboarding don't just linger. They compound.

"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 at these hyperscale AI companies," Justin says. "There's no room for knowledge gaps. There's no room for misinformation."

Legora's legal tech complexity makes this especially critical. An AE who gets on a call and starts talking about litigation law to an M&A attorney will lose credibility instantly. The ramp program has to compress that domain knowledge without shortcuts.

At Legora, onboarding is everyone's job on the enablement team, not a single person's. Each team member owns a piece of the enablement roadmap and is accountable for ensuring their piece is accurately represented in the ramp program.

Multi-week certifications track specific metrics, but the real audience isn't the new hire—it's their manager. The goal is to surface exactly where someone is strong and where they're soft, so managers can prioritize their limited coaching time accordingly.

"At the rate we're growing, if you're not obsessing over your onboarding program, you ain't doing it right. New paradigms require new paradigms."

Certification should happen in the field, not in a role play

Justin's view on certification stems from a simple observation: everyone knows how to game a role-play.

Reps share the canned questions in advance, prepare polished scripts, and deliver performances that look nothing like how they actually sell.

His approach to certifications has two layers.

Field readiness: Can you demonstrate enough competence to get in front of customers?
Field performance: What happens when you're actually on a call and the prospect clearly doesn't want to be there?

"There's just such a big delta between a performative cert and what they do in front of customers," Justin says.

His preferred method is what he calls team certifications: after a training, the manager brings three or four real scenarios into the next team call and walks through them as a group. It's organic. It maps to what reps actually face. And managers can tell immediately whether the team is internalizing the material or falling back on old habits.

Justin's team has started using AI agents to make these scenarios even sharper.

At Legora's sales kickoff, they fed workshop transcripts into an agent that generated discussion scenarios based on real customer anecdotes people had shared in the room. No hypotheticals—just actual situations their peers had described, repackaged as "what would you do if" prompts for managers to run with their teams.

"You're going to spend days obsessing over this demo. Meanwhile, you are just another call on their calendar for that day. Maybe their kid got suspended from school. How much do they care about your demo right now?"

That's exactly why certification has to take place in real sales conditions, not in controlled environments.

A rep who can deliver a polished pitch to their manager might completely miss that a prospect needs to hear about one specific use case, not a full product tour. The only way to know if someone can read the room and adapt is to watch them do it with a real customer.

Be the guardian of organizational calories

At most companies, cross-functional collaboration means a weekly sync and a shared Slack channel. Justin thinks about it more like running a record label.

Product marketing, product, innovation teams—they're the artists. Enablement is the 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."

In practice, that means sequencing. Listening audiences have limited attention. So you don't want your top two artists releasing records on the same day. They'll both sell, but not as well as they could have.

The same logic applies to sales enablement.

When product marketing wants to release new messaging with five selling weeks left in the year, Justin pushes back—not because the messaging is bad, but because the timing will burn organizational calories.

"I've seen product marketing messaging released without the proper rollout and implementation to the field. If the field doesn't understand it, they don't pitch it with confidence, it gets rejected, and then you wind up in this cycle of wasted organizational calories."

Justin's broader point is about messenger and medium. If enablement posts everything, it becomes noise. When the VP of Product shares a product update, people pay attention. When the CRO delivers the pitch himself, reps take it seriously. Enablement's job isn't to be the messenger—it's to orchestrate who delivers what, when, and how.

"When we launched new messaging here at Legora, our CRO delivered it via Loom, and 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."

He's also a vocal proponent of documentation. Program guides, roadmaps, role definitions—"initially it's like, wow, this is a lot of slides. But I am here to tell you: slides save lives."

The investment pays off in trust. When cross-functional stakeholders can see the plan, understand their role, and track progress, the politics dissolve.

When you can't get training time, make the training invisible

Every enablement leader has been told there's no room on the calendar. Justin's answer: stop asking for time and start embedding in the tools the field already uses.

Back when Justin was leading enablement for the launch of Slack Canvas, the timing was brutal. Slack's sales team was integrating into Salesforce's org—so the training calendar was full. Canvas was supposed to launch that same month.

Justin asked for a few hours of field training time. His head of field enablement's response: "Ain't no way."

So Justin pivoted. If he couldn't get time with the field, he'd build the enablement into the tool itself.

He learned Slack Canvas inside and out and built an "enablement hub"—everything reps needed to know about Canvas, delivered inside a Canvas.

The initial launch wasn't promising. "The emoji rate on the launch message was not great," Justin says. "I thought I was heading toward the bread line." But when he pulled adoption data from the product team, the Canvas hub had driven 400% more traffic in its first month than the Highspot page they'd built.

What happened next snowballed. Justin trained Slack's entire 600-person global enablement org on Canvas.

The org pivoted its whole approach—Slack Canvases became the front door for all enablement at both Slack and Salesforce. The Chief Product Officer featured the enablement hub in his Dreamforce keynote. Denise Dresser showcased it in her company kickoff.

The lesson isn't really about Slack Canvas. It's about what happens when enablement stops waiting for permission and starts building where the field already works.