Director, Revenue Strategy & Operations

Yoodli AI Roleplays; Kirkland (WA); Hybrid; USD 200,000 - 240,000; Full time

Benefits offered by this job

Hybrid work Seattle HQ

Equity opportunities

Job summary

Yoodli AI Roleplays seeks a senior leader for Revenue Strategy, Planning & Operations to scale a data-driven GTM organization. You will own the rhythm of business, drive quota and territory design, and partner across Finance, Sales, and executives to translate analytics into action.

You will lead Revenue Systems and Analytics, hire key talent, and shape processes that optimize performance while leveraging modern GTM tech. This is a hybrid role based in Seattle with strong equity opportunities.

Qualifications

• 8-12 years in revenue operations, GTM strategy & operations
• Direct experience with quota and comp modeling
• Cross-functional leadership across GTM, Finance, and executives

Responsibilities

• Own the GTM rhythm with weekly to annual cadences and reviews.
• Partner with the CRO to structure and segment for 2027, directing analytics.
• Frame hard questions and drive decisions with data, ensuring execution.
• Build a master data foundation and design scalable territories.
• Model quota and comp scenarios and enable a forecast cadence.
• Oversee Revenue Systems and hire the Senior Revenue Analyst, partnering with Finance.

Skills

Revenue operations

GTM strategy

Quota modeling

Territory design

Forecasting

Cross-functional leadership

HubSpot/Salesforce

Analytics tooling

Education

Bachelor's degree or equivalent experience

Tools

HubSpot

Salesforce

Job description

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 ( www.yoodli.ai/press ). You can try the platform for free at www.yoodli.ai 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 May 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
• 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

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