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Who we are:

Reports to: Josh Vitello, Chief Revenue Officer

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 experiential learning

The Role: Enterprise Sales Leader

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

• Team Leadership
  • 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
• Sales Execution & Forecasting
  • 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

You’re a Fit If You…

• 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–$360,000) + meaningful equity
  • Full benefits: healthcare, dental, vision, 401k, unlimited PTO
• 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