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.
We’re hiring an Enterprise Sales Leader to build and scale Yoodli’s enterprise sales motion as a key member of the GTM leadership team. You’ll report to the Head of GTM with board-level visibility and play a critical role in shaping how we land strategic logos, expand across the enterprise, and define what “great” looks like in a new category.
You’ll lead a team of high-performing Account Executives (initially 3–6), while also personally engaging in strategic enterprise deals. This is a player-coach role: you’ll set vision and structure while remaining hands-on in the field, modeling excellence in account planning, multithreaded execution, and consultative selling.
You’ll collaborate closely with Product, Customer Success, and Marketing to refine our positioning, establish repeatable playbooks, and ensure Yoodli becomes the must-have skills layer for high-performing GTM teams and beyond.
What You’ll Do
Recruit, develop, and retain top-performing Enterprise AEs
Coach on pipeline generation, discovery, and negotiation discipline
Build a culture of accountability, humility, and continuous improvement – using Yoodli itself as a coaching tool
Drive pipeline generation, progression, and quota attainment
Forecast accurately with visibility into coverage, stage health, and risk
Apply structured deal inspection and sales methodologies (e.g., MEDDIC, Challenger) as core principles guiding how the team qualifies, strategizes, and closes
Uplevel the team’s ability to transform inbound interest into strategic, account-based wins
Cross-Functional Partnership
Collaborate with Product, CS, and Enablement to influence roadmap and drive customer success
Partner with Marketing to develop industry-specific plays and messaging
Work closely with RevOps to refine systems, dashboards, and KPIs
Have 2–5 years of experience managing high-performing enterprise AEs
Consistently exceeded $1M+ quotas through structured planning and complex sales execution
Balance deal discipline with emotional intelligence and storytelling
Have implemented and scaled sales methodologies (e.g., MEDDIC, Challenger)
Embrace systems and process without over-engineering
Care deeply about communication, learning, and the potential of AI to unlock performance
Thrive in fast-paced, early-stage environments
Bonus Points
Experience selling in the sales & HR tech stack (e.g., revenue intelligence, L&D, talent enablement)
Track record across both early-stage (Seed–Series C) and scaled GTM organizations
Exposure to PLG or product-led sales environments
Why Yoodli
Competitive compensation (OTE: $300,000–$380,000) + meaningful equity
High-impact, mission-driven work with direct customer feedback loops
Work with a humble, driven, deeply collaborative team
Hybrid schedule: 3 days in-office at our Seattle HQ (lunch included) + 2 days remote
A product you’ll use and believe in – every single week
How to Apply:
Does this role sound like a good fit? Email us at Please include the role’s title in the subject line and attach or link to your resume.
#J-18808-Ljbffr