Director, Revenue Strategy & Operations

Madrona Venture Labs; Seattle (WA); Hybrid; USD 200,000 - 240,000; Full time

Benefits offered by this job

Equity opportunities

Competitive compensation

OTE $200-240K

Job summary

Yoodli, an AI-powered experiential learning platform, seeks an Operations leader to build and run Revenue Strategy & Operations as we scale. You’ll sit close to the CRO as a thought partner and chief of staff for GTM, leading a small team including Revenue Systems and Analytics & Insights.

This hybrid role requires 3 days in-office at Seattle HQ and 2 days remote, reporting to the CRO and working with Finance, FP&A, and Partnerships.

Qualifications

• 8–12 years in revenue operations, GTM strategy & operations, or sales/business operations in a senior/leadership role.
• 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.
• B2B SaaS or B2B AI experience preferred.

Responsibilities

• Run the business. Own the GTM rhythm of business (weekly through annual cadence, monthly and quarterly reviews).
• Change the business. Partner with the CRO on quota distribution, direct vs. channel, and investments for 2027; set analytics agenda.
• Decisions, end to end. Frame hard questions, drive data-backed decisions, ensure execution.
• Territory and coverage. Design customer master data foundations and rampable territories.
• Planning and forecasting. Model quota and comp, enable a forecast cadence with accountability.
• Team and cross-functional partnership. Lead the Revenue Systems domain and hire the Analytics & Insights Lead; partner with Finance, FP&A, Deal Desk, Partnerships, Marketing, and GTM leaders.

Skills

GTM strategy & ops

Data-driven decision making

Systems thinking

Cross-functional leadership

Quota & comp modeling

Forecasting

Sales analytics

Education

Bachelor's degree or equivalent experience

Tools

HubSpot

Salesforce

Job description

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 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.

The Role

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.

What You'll Do

• 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

What we're hoping you bring

• 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

You Might Be a Fit If You...

• 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

Extra credit 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)

Why Yoodli

• 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!)