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 a Mid-Market Sales Leader to build and lead the team that drives Yoodli's fastest-growing segment. You'll report to the Head of GTM and own the number for mid-market, the segment that sits between our high-velocity SMB motion and our strategic Enterprise motion.
What they're looking for
- Recruit, develop, and retain top-performing Mid-Market AEs
- Coach reps on discovery, multi-threading, demo execution, and negotiation
- Run weekly 1:1s, deal reviews, and pipeline reviews with rigor
- Build a culture of accountability, curiosity, and continuous improvement, using Yoodli itself as a coaching tool
- Own the mid-market number, including pipeline generation, progression, and quota attainment
- Forecast accurately with clear visibility into coverage, stage health, and risk
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, Toastmasters, and Dale Carnegie 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 $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...
Browse similar: AI jobs · AI startup jobs · Startup jobs · Remote jobs