Head of GTM Strategy and Operations
Workwhile
Head of GTM Strategy and Operations
Workwhile
Connects vetted hourly workers with businesses
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.
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.
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.
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.
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)
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!
WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply.
WorkWhile connects businesses that need hourly workers with vetted labor in sectors like warehouse, light industrial, last-mile delivery, event services, food production, and hospitality. The platform uses advanced screening and background checks to verify workers and lets businesses set an hourly rate for each worker, paying only for filled jobs. The system enables flexible staffing, letting companies scale labor up or down as needed. Workers can manage pay, schedules, and preferences via a mobile app, including next-day pay to shorten the typical payday delay. Revenue comes from charging businesses for the labor provided, with no upfront costs, hidden fees, or long-term contracts. The goal is to efficiently match demand for hourly labor with a reliable, vetted workforce while giving both sides flexibility and cost control.
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