About this Director of Customer Education role at Yoodli AI Roleplays
Who we are
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.
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.
Reporting to the co-founder and Chief Customer Officer, this role sits at the intersection of customer experience, enablement, and revenue outcomes. You will work across Customer Success, Support, Product, Sales, and Marketing teams to build education programs that accelerate adoption, improve customer outcomes, support expansion opportunities, and help enterprise customers successfully operationalize Yoodli at scale.
Your job will be to turn customer and partner education into a repeatable engine. You'll build the programs, content, and systems that help customers drive adoption inside their organizations, keep them current with everything we ship, and scale enablement across the entire customer base.
This is incredibly important to us because we sell to L&D and enablement leaders whose entire job is education: they will assess our rollout against the standard of their own programs. Yoodli aims to create value when people practice repeatedly, see their skills improve over time, and reflect. Teaching customers and partners how to run a great program is part of how the product delivers.
To start, this is a hands-on role. You won’t just define the education strategy: you’ll help build the operating model, create scalable learning experiences, support strategic enterprise implementations, and develop a global training capability that grows with the business.
What you'll do
- Build and maintain the core library: onboarding pathways, self-paced modules, video walkthroughs, guides, templates, product academies, and live workshops
- Own customer and partner education for every launch, alpha through GA. That includes internal readiness, so CS, Support, and Sales are fluent before customers see anything, and that keeps pace with how fast we ship: customers and partners should always know what's new, why it matters, and how to use it (in conjunction with Customer Marketing)
- Build the program-admin track and certification paths that teach customers and partners to launch and run a Yoodli program inside their org
- Segment deliberately: Decide which launches and accounts earn white-glove treatment (working sessions, webinars) and which are served by scaled programs
- Measure impact through adoption, time-to-value, and support deflection, and iterate on what the data says
- Grow the function as the work proves out: You'll start as the team, then make the case for headcount and hire against where the function needs depth
What we'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
- High agency in ambiguity, and excellent writing. Most of this job is making complicated things feel simple
- Series B to Series D SaaS, or a comparably fast-scaling environment
Nice to have
- A background in L&D, corporate training, or communication coaching. You’ve designed first of its kind programs that pushed learning forward in new and innovative ways
- Experience crafting education programs for partner enablement and how those differ from traditional customer enablement
- Experience adapting onboarding programs for a variety of industries (e.g. healthcare vs higher ed)
- Experience with digital adoption or in-product guidance tooling
- You’ve built a customer community or user group alongside a formal curriculum
Why join
- A rare first-hire mandate: you define what customer education means at Yoodli, with direct access to the founders and visibility across every team
- Education is our thesis. We sell experiential learning, so how we teach our own customers is the proof that it works
- Real leverage: what you build shows up in adoption and renewal numbers, and you’ll have the instrumentation to prove it
- A team that believes people learn by doing, and will give you the room to build that conviction into how we serve customers
Compensation and location
- Total compensation is targeted at $195,000 - $210,000 USD (depending on location and experience)
- Equity opportunities at a fast growing company
- Health, dental, vision insurance
- 401k plans
- Unlimited PTO, free lunches at the office (if you’re based in Seattle)
- US-based opportunity, Seattle (preferred) or San Francisco (remote)
Yoodli is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.
