Lyra Health’s AI Roleplay Playbook: Takeaways from SEC SF

Betting on humans in the age of AI

At Yoodli, we believe companies will win on the strength of their people. AI doesn’t replace that. It should make every rep, manager, and expert better at the conversations that matter.

That was the thread running through our session at the Sales Enablement Collective in San Francisco last week. Yoodli CEO and co-founder Varun Puri shared the stage with Brianna Lewke, Sr. Director of GTM Enablement at Lyra Health, in front of 60+ enablement leaders. Brianna brought the view from inside a fast-growing healthcare company. Below are the ideas we heard land hardest in the room.

The enablement problem: completion isn’t comprehension

Most enablement teams are small, and the list of audiences keeps growing. New teams need to ramp, existing teams need new skills, and every launch needs reps who can actually explain it. Brianna described it as needing to do more with less, right now.

The traditional certification workflow doesn’t scale to that. An LMS upload, a Gong review, a manager-scheduled call, a spreadsheet rubric, and a round of reminders, repeated for every cert. Enablement can’t clone itself, and managers don’t have the time.

The fix isn’t more content. It’s changing what gets measured: from who finished the module to who can actually have the conversation.

What to look for in an AI roleplay partner

Brianna shared the three criteria she used, and they hold up for any enablement leader evaluating AI sales training:

1. Enterprise trust. In a regulated industry like healthcare, security and compliance come first.
2. Flexibility. The platform should fit your methodology, integrate with your systems, and scale across use cases.
3. Partnership. Look for a vendor that solves today’s problem and helps you see what AI can do for enablement next, with a real customer community and a CSM behind it.

Her tactics for testing those were simple: backchannel references, a small pilot, and seeing how well the vendor works with your executives.

Learn, practice, certify: the model that scales

The setup Brianna demoed follows a pattern we see working across Yoodli customers. It makes training engaging for reps and measurable for revenue leaders.

1. Learn with an AI Tutor. Reps get up to speed on a new feature or release.
2. Practice with AI Roleplay. They pitch it out loud against a realistic buyer until it sounds natural.
3. Certify and measure. Post-call coaching, manager QA, and follow-up learning close the loop.

The difference from traditional training is that practice connects to the real conversations reps are about to have, not a generic script.

Measure outcomes, not attendance

The strongest programs roll out in stages (crawl, walk, run) and measure something different at each one:

• Pilot: engagement. Are people practicing, and how much?
• Certifications: skills and confidence. Are reps measurably better after practice than before?
• Scaled programs: business impact. Does the training show up in pipeline and revenue in the CRM?

That progression is what turns enablement from a cost center into a line item leadership wants more of. One of the best signals Brianna described wasn’t a metric at all: other teams started asking to be next.

Three AI roleplay plays worth stealing

Just-in-time demo certification. Swap the traditional pitch cert for an interactive, screen-share demo cert. Reps practice live clicks and platform navigation right before they need it, which helps less demo-confident sellers get fluent on complex products faster.

Multi-persona practice. Yoodli’s multiplayer mode lets reps rehearse deals with several stakeholders at once, including internal and external SMEs. Simulating a finalist meeting that goes off track builds the muscle memory to keep the real one on course.

Enablement beyond sales. Subject-matter experts outside the revenue team can use the same practice loop. Brianna’s version started from a single 15-minute conversation with her CRO, runs fully async, and took off because executives went through it first.

Honest lessons from the stage

Brianna was candid about the hard parts, which is what made the session useful.

• It’s stressful for some people. AI roleplay isn’t comfortable for everyone on day one, and it arrives when everything else is changing too.
• Embed it in the flow of work early. Bring practice to reps inside the CRM and Gong instead of asking them to go somewhere new.
• Pace the innovation. New features keep shipping, and teams need room to absorb one before the next arrives.

Her advice for enablement leaders getting started:

1. Pick a partner with a point of view. Ask what they believe about the near term and the long term. Make sure they have a thesis at all.
2. Choose an end-to-end platform. One system that covers onboarding, manager training, customer enablement, demo certification, and AI tool fluency.
3. Use the tech yourself. Don’t stop at the demo. Get into the platform and build something.

That’s where Yoodli is headed too, with live call coaching and everboarding that keep skill development going long after onboarding ends.

FAQ

What is AI roleplay for sales enablement? AI roleplay lets reps practice real conversations, like pitches, demos, and objection handling, with an AI buyer and get instant feedback. Yoodli pairs it with an AI tutor and certification so enablement teams can measure skill, not just completion.

How do you measure the impact of AI sales training? Start with engagement in a pilot, then measure skill and confidence change through certifications, then connect scaled programs to pipeline and revenue in your CRM.

Is AI roleplay safe for regulated industries like healthcare? It can be, with the right vendor. Make enterprise trust the first evaluation criterion, check references, and run a small pilot before rolling out.

What is just-in-time demo certification? It replaces a standard pitch cert with an interactive, screen-share demo that reps practice right before they need it, including live clicks and platform navigation.

What is the Sales Enablement Collective? A community of enablement leaders that hosts in-person events. Yoodli got its start in the SEC community.

Thank you, SEC

The Sales Enablement Collective is where Yoodli got its start, so being back in that room with so many customers and friends meant a lot. Thank you to Brianna and the Lyra Health team for sharing their work so openly, and to Kyle Del Francia, Meg Cory, and Diana Cappello for running the Yoodli booth.

Want to see how AI roleplay could work for your team? Book a demo to talk with us.