Director, Revenue Strategy & Operations

Yoodli is an AI-powered experiential learning platform that uses AI roleplays to personalize real-life practice and transform how organizations learn and prepare. We're pioneering a new category — AI Roleplays — because we believe nobody should miss out on the opportunities they deserve because of how they communicate. Static content doesn't create behavioral change. Practice does.

We've raised $60M — including a $40M Series B led by West Bridge Capital — backed by Madrona, Neotribe, Cercano, and incubated at the Allen Institute for AI. Our customers include Google Cloud, Snowflake, Databricks, Ring Central, SAP, Franklin Covey, Korn Ferry, Sandler Training, Toastmasters, and many more — with learners in over 150 countries. We're headquartered in the heart of Seattle, and we're having a lot of fun along the way.

We value humility
, a bias for action
, and the belief that we win together
.

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This is the first dedicated operations leadership role in the company's history. You'll build the Revenue Strategy & Operations function and run it as we scale, sitting close to the CRO as a thought partner and chief of staff for GTM. This is 0-to-1 on professionalizing how a fast-growing revenue org decides, operates, and plans — not on systems, which we already run well.

You'll lead a small team:
Revenue Systems, already in seat with Matt Wepner owning our GTM stack and consultancies, and a Revenue Analytics & Insights Lead you'll hire.

This is a Hybrid role: 3 days in-office at our Seattle HQ (lunch included) + 2 days remote.

• Run the business. Own the GTM rhythm of business (weekly through annual cadence, monthly and quarterly business reviews), take decisions off the table, and keep every GTM leader focused on their core work with minimal administrative load
• Change the business. Partner with the CRO on how we structure and segment for 2027: quota distribution, direct vs. channel, and where we invest. This sets the agenda for the analytics function
• Decisions, end to end. Frame the hard questions (segment cut lines, BDR pilot-to-program, regionalize vs. verticalize, strategic accounts, land-and-expand), drive them to a decision with data underneath, and make sure they land in execution
• Territory and coverage. Stand up the customer master data foundation we lack today, then design territories that are fair and rampable rather than inherited
• Planning and forecasting. Model quota and comp scenarios and recommend (CRO and CFO approve). Enable a forecast cadence where sales leaders own their numbers independently, with a Sales Ops forecast as a check
• Team and cross-functional partnership. Own the Revenue Systems domain (Matt Wepner) and hire and direct the Analytics & Insights Lead. Partner tightly with Finance, FP&A, Deal Desk (owned by Finance), Partnerships, Marketing, sales leadership, and our founders

• Mission alignment: You believe in our vision and care deeply about helping people achieve more by communicating better
• Decision-making at scale: You frame hard questions, drive them to a decision with data underneath, and make sure they land in execution — not just produce decks
• Systems thinking: You hold a clear point of view and turn analysis into operational change across a fast-growing revenue org
• Cross-functional leadership: You partner naturally across GTM, Finance, and executive stakeholders, and know how to direct systems and analytics work rather than execute it yourself
• Craft and rigor: You bring hands‑on fluency with quota and comp modeling, territory design, and forecast operations, and you hold a high bar for how decisions get made and operationalized

• 8-12 years in revenue operations, GTM strategy &…