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 behavior change. Practice does.
We've raised $60M — including a $40M Series B led by WestBridge Capital — backed by Madrona, Neotribe, Cercano, and incubated at the Allen Institute for AI. Our customers include Google Cloud, Snowflake, Databricks, RingCentral, SAP, FranklinCovey, KornFerry, 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.
Try the platform free at yoodli.ai.
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 SalesOps 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 & operations, or sales/business operations, with progressive scope and time in a senior or leadership seat
Direct, hands-on experience with quota and comp modeling, territory design, and forecast operations
Demonstrated cross-functional leadership across GTM, Finance, and executive stakeholders, including managing third-party resources
Fluency with a modern GTM stack (HubSpot or Salesforce) and analytics tooling
A track record of turning analysis into operational change, not just producing decks
B2B SaaS or B2B AI experience
Bachelor's degree or equivalent experience
You've built or substantially rebuilt a StratOps function 0-to-1
You've scaled a revenue org through a comparable curve (roughly $20M to $70M+ ARR)
Huge impact opportunity: build the first dedicated operations function at a fast-growing startup, reporting directly to the CRO
Competitive compensation: significant equity opportunities at a venture-backed company
Compensation: $200-240K OTE
Work directly with the CRO and founding team to shape how Yoodli's revenue org scales
Join a fun, inclusive, and highly motivated team culture (and help define it!)
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Yoodli is a Seattle-based AI communication coaching company offering an enterprise roleplay platform where employees practice sales pitches, demos, and difficult conversations with AI and receive real-time feedback. It serves sales enablement and L&D teams at enterprises.
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