VP of Product

Who We Are Yoodli is the AI roleplay simulator redefining how individuals and teams master communication. We’re building a new category: AI Roleplays, an experiential learning platform that helps people improve through lifelike simulations powered by generative AI. 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, Toastmasters, and BDO 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’ve raised over $20M, are doubling our team in 2025, and are headquartered at the beautiful Pier 70 in Seattle. https://www.youtube.com/watch?v=9CVsdayG2kw https://yoodli.ai/blog/yoodli-ai-roleplays The Role:  We’re hiring our VP of Product, a hands-on leader and doer who will drive Yoodli’s product strategy, vision, and execution as a key member of the leadership team. You’ll report directly to the CEO with board-level visibility. Product management and design will report to you, but we expect you to run a lean, nimble team that thrives on speed and clarity. You’ll be responsible for shaping the future of AI roleplays: defining the roadmap, simplifying complexity into elegant experiences, and ensuring Yoodli delights both enterprise buyers and individual users. You’ll set the vision and also roll up your sleeves - running discovery calls, writing PRDs, digging into analytics, and collaborating with design, engineering, and customer success teams to ship quickly. This is a rare chance to define a new category at the intersection of AI, learning, and communication. We expect you’ll dive into the product, form sharp opinions, and push our broader strategy forward. What You’ll Do Own and articulate the product strategy and vision that positions Yoodli as the intelligent skills layer for GTM teams and beyond Lead and grow a small but mighty product + design team Translate customer insights into a clear roadmap, balancing enterprise and PLG user needs Partner with engineering, GTM, and leadership to ensure alignment from strategy through launch Drive rapid experimentation and make speed our superpower Instrument and analyze product data using tools like Google Analytics, Amplitude, and session monitoring platforms Ship fast. Simplify. Prioritize clarity over feature bloat Be the voice of the customer in every leadership conversation You’re a Fit If You… Have 8+ years of product experience, including 3+ years leading PMs and/or designers Have scaled product functions at a fast-moving startup (Seed–Series C preferred). Ideally 0-50M ARR Flex naturally between big-picture strategy and hands-on execution Thrive on simplicity,  complexity into intuitive product experiences Are energized by in-person collaboration at AI House in Seattle Care deeply about communication, learning, and the potential of AI to unlock human performance Are fluent in generative AI and generative AI experiences Bonus Points Experience with PLG and enterprise sales motions Background in sales enablement, learning platforms, or coaching tools What’s in it for you? Huge impact opportunity: Build and scale a company from the ground up Competitive compensation: Equity opportunities at a venture-backed startup Base compensation: $190K-$250K Work on a daily basis with the founding team and mentors Join a fun, inclusive and highly motivated team culture (and help define it!) Offices: Seattle, Washington, United States (Seattle HQ);