Enterprise AI roleplay platform for sales enablement, partner training, and L&D. Practice pitches, demos & crucial conversations. Trusted by Google, Sandler, Korn Ferry + more. Backed by Madrona.
About the role
We’re hiring our first Director of Customer Education to define and build how Yoodli’s global customer and partner base learn, adopt, and succeed with Yoodli’s AI Experiential Learning platform.
What they're looking for
- 5-8+ years in customer education, enablement, instructional design, or customer success at a B2B SaaS company, including at least one function you built from scratch rather than inherited
- Hands-on across formats: You've personally scripted and recorded video, designed assessments, led webinars, shipped a certification program, written the guides, and run the live sessions
- You tie education to business outcomes, not completion rates. You're comfortable pulling your own data, defining metrics that don't exist yet, instrumenting them, and reporting them to executives
- AI first mindset in everything you do, from content creation to tooling design to maintenance. Sharp instincts on what elements AI can help scale and which should remain human led
- Strong at cross-functional influence. You’ve worked across Customer Success, Product, Marketing, and Support, including on launches, and you know how to drive work through teams you don't manage
- Experience educating enterprise program owners who roll out to hundreds or thousands of users
More about this role
Yoodli is the AI roleplay simulator redefining how individuals and teams master communication. Think of it as the batting cage before the big game - but for communication. Whether it’s a sales pitch, manager feedback session, or media interview, Yoodli provides private, judgment-free, just-in-time coaching. Leaders at companies like Google, Databricks, Snowflake, RingCentral, and Toastmasters use Yoodli to ramp reps faster, improve message delivery, and reduce coaching burden on frontline managers. The result is stronger performance, greater team readiness, and a more scalable path to impact.
We’re building a new category called Experiential Learning: a new AI-powered category that helps people learn through conversational roleplays. People don’t learn from slides: they learn through dialogue, questions, and iteration. Yoodli makes that process interactive, personalized, and always up to date. It’s learning that feels fun, builds confidence, and finally lets organizations measure the ROI of training.
We’ve raised $40M in Series B funding, doubling our team in 2026, and are headquartered at the beautiful Pier 70 in Seattle.
- TED Talk with our “Why”
- Explainer on experiential...
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