Head of GTM Strategy and Ops
- Compensation
- Not disclosed
- Location
- San Francisco
- Work setup
- Hybrid
- Seniority
- C level
- Employment
- Not specified
- Experience
- 3+ years
- Category
- Not specified
- Posted
Skills
Must have
- 7+ years in Revenue, Sales, or Business Operations or GTM Strategy, including building and leading teams (roughly 3+ years managing).
- You’ve helped scale a high-growth business through a comparable inflection - think roughly $20M to $100M+ in revenue - in a marketplace, workforce, or B2B SaaS environment. Two-sided marketplace or wo
- Strong, hands-on analytical ability: you get into the data yourself (SQL and BI/dashboards, e.g., Metabase) to model, diagnose, and pressure-test - not just direct others to.
- Deep fluency with the modern GTM stack - enough Salesforce and systems-architecture judgment to design, audit, and lead the build (a systems & tooling lead reports to you for hands-on administration).
- An AI-native operator: you’ve used predictive/AI and prompt-engineered tools (Claude, Clay, and the like) to remove operational drag and create leverage.
- A collaborative, high-velocity, low-ego style, with the executive presence and crisp written communication to earn trust with the sales floor, the C-suite, and the board alike.
Nice to have
- Prior quota-carrying or customer-facing experience (empathy for the teams you support).
- Experience standing up RevOps or forecasting in a business moving from ad hoc to systematized.
- Exposure to capital-linked unit economics (receivables, margin) or regulated/frontline labor.
Full description
About WorkWhile
WorkWhile is the AI-native labor platform modernizing the frontline economy. Our digital marketplace connects vetted, reliable hourly workers with on-demand shifts across major verticals like logistics, light industrial, warehousing, hospitality, and retail. Businesses get access to a quality workforce, while workers get stable income and unmatched benefits, including next day pay, free telehealth services, and financial services.
We have the audacious goal to align incentives and solve inefficiencies in the labor market, disrupting the $650 billion staffing and recruiting market. Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, WorkWhile is reshaping the future of work.
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The Role
We’re building the commercial engine that takes WorkWhile from strong-but-ad-hoc to a repeatable, data-driven growth machine - and this role is the strategic and operational core of it. Reporting directly to the Chief Business Officer, you’ll be our right hand on GTM strategy and operations: the person who turns a scaling revenue org into a cohesive operating system that produces predictable, defensible growth.
This is a builder’s seat, not a maintainer’s. You’ll inherit a small, capable team and grow it into three functions - operations for our new-business (AE) motion, operations for our expansion (AM/CS) motion, and systems & tooling - while personally owning the hardest strategy and modeling problems yourself. And because we’re a two-sided marketplace, your forecasts and plans have to reconcile demand (pipeline, quota, conversion) with supply (fill rate, worker reliability, capacity): a number we can’t fill isn’t a number. If you’re energized by ambiguity, love both the whiteboard and the SQL query, and want your fingerprints on how a category-defining company scales, this is a rare one.
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What you’ll own
- The revenue operating system. Own the end-to-end GTM cadence - weekly forecast, monthly and quarterly business reviews - and deliver a single, methodology-backed forecast leadership and the board can act on. Build it to reconcile demand-side pipeline with marketplace supply and fill, so the number is one we can actually deliver.
- GTM strategy & motion design. Drive the highest-leverage commercial bets: segmentation and named-account focus, intent capture, outbound and conversion levers, pricing and packaging recommendations, and deal desk. Codify what our best sellers and account managers do into a motion the whole team can run.
- Planning & performance. Partner with Finance to design fair, motivating incentive structures tied to the behavior we want - profitable growth and durable expansion, not just volume. Partner with Finance and pod leads on territory design, quota-setting, and capacity modeling, and build the account-level forecast the business plans against.