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Director, Revenue Strategy & Operations

$200k - $240k

Yoodli AI Roleplays

Yoodli helps people get measurably better in their careers. We help individuals achieve this by helping them land their job, onboard at their companies, learn new skills, practice a speech, sales pitch or difficult conversation, and then take your Yoodli coach with you from one role to the next. For organizations, this means helping you upskill your entire workforce for the AI Future.

We’ve always believed in the human potential. In 2021, Esha and Varun started Yoodli as an AI communication coach - to help people communicate with confidence. Since then, our users have used Yoodli for so much more: to learn new concepts through AI Roleplays, practice different kinds of conversations (sales pitches, job interviews, manager conversations), and even use Yoodli as their personal coach to help them learn to use Gemini, Claude or other AI Tools. It’s why we expanded our technology to be the AI Platform for Human Skills.

Who We Are

Our team includes former employees from Google, Apple, Microsoft, Tableau, and beyond, united by a passion for empowering people using AI. We're headquartered in the heart of Seattle, and we're having a lot of fun along the way. Our culture is built on failing fast, iterating constantly, and taking bold bets. We value humility, authenticity, and a can-do-attitude.

We’re backed by Madrona, Neotribe the Allen Institute for AI, Cercano, and have raised over $60M to date.

Our customers include Google, RingCentral, Databricks, Snowflake, Sandler Sales, Dale Carnegie, Toastmasters, and users in over 150 countries. We’ve been featured in Forbes, Fortune, WSJ, Geekwire, ZDNet, and several other outlets ( ). You can try the platform for free at and learn more about us in this TED Talk .

The Role

This is a leadership role over Revenue Strategy, Planning & Operations. You'll take an established function to its next level and run it as we scale.

Our Revenue Operations team has built a strong systems foundation: HubSpot, Common Room, Intercom, and a modern GTM stack that runs well. What we're adding is the strategy, planning, and insights layer on top of it. The capability to see the business clearly, decide well, and operationalize the decisions we make.

Your mission is an operationally excellent revenue organization that runs on data. You'll own the rhythm of the business, meaning the planning cycles, the forums, and the cadences that let a fast-growing GTM org decide and follow through. You'll build an analytics and insights operation that turns systems data into direction. And you'll put AI and those insights to work so every minute of GTM time goes toward customer impact and outcomes.

You report to the CRO and act as a thought partner on how the revenue org operates. You'll lead a small team: Revenue Systems, already in seat and owning our GTM stack and consultancy relationships, and a Revenue Analytics & Insights Lead you'll hire.

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. Oversee the Revenue Systems domain leader and hire the Senior Revenue Analyst. 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 operationsDemonstrated 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 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!)
  • This is a Hybrid role: 3 days in‑office at our Seattle HQ (lunch included) + 2 days remote. #LI-Hybrid

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey.Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiringprocess or thereafter. Any information that you do provide will be recorded and maintained in aconfidential file.

As set forth in Yoodli AI Roleplays’s Equal Employment Opportunity policy,we do not discriminate on the basis of any protected group status under any applicable law.

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection.As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measurethe effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categoriesis as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

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