Head of GTM Strategy and Ops

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.

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.
• Systems, data & AI. Own the GTM tech stack (Salesforce, Nooks, Gong, Hightouch, Clay, and our BI layer) and the pipelines and dashboards beneath it. Embed AI across the funnel - account scoring, enrichment, intent, call intelligence, and routing - so the team spends its time where it converts and our data stays clean enough to trust.
• Cross-functional leadership. Be the connective tissue across Sales, Account Management, Marketing, Finance, Product, and Marketplace Operations - representing GTM’s priorities and translating between the commercial number and the marketplace that has to fill it.
• Team building. Recruit, coach, and scale a high-performing team across the three RevOps functions, and set the roadmap for how Strategy & Operations supports the company’s growth.

What Success Looks Like

In your first 6-12 months, you’ll have stood up a forecast the board trusts, shipped an incentive plan aligned to profitable growth, replaced spreadsheet heroics with a real operating rhythm across our Top-20 and expansion accounts, and gotten our data and systems clean enough that decisions come from one source of truth.

About You

This is a high-bar role, and we’ve tried to be honest about what actually predicts success here rather than pile on filters. You likely bring most of the following.

• Must-haves
• 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 workforce-platform experience is a plus, because supply-aware GTM is a different game.
• 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-haves

• 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.

Benefits & Perks

• Competitive base salary and bonus
• Equity
• Hybrid work culture with office hubs in SF, NY, Seattle & Toronto
• In-person company offsites
• Medical, dental, & vision coverage
• Flexible time off
• 401(k) with employer match
• WFH stipend to support your home office needs

WorkWhile has a diverse, mission-driven, and supportive culture-we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!