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.
The Role
As the Head of GTM Strategy & Operations, you will be the strategic engine powering our multi-segment Go-To-Market (GTM) machine. You will transition our scaling revenue operations from manual processes into a highly automated, cohesive revenue operating system that fuels predictable, data-driven company growth.
Key Responsibilities
GTM Motion Enablement & Evolution: Drive strategy for projects such as capturing intent signals, outbound sequence best practices, deal conversion levers, pricing strategy and deal desk.
Revenue Operating System: Own and manage the end-to-end GTM cadence, including weekly forecasting models, monthly business reviews, and quarterly business reviews (QBRs). Deliver a single, methodology-backed forecast for leadership and investors.
Systems & Technology: End-to-end ownership of our GTM tech stack (Salesforce, Nooks, Gong, HighTouch, and Clay). Automate core pipeline architectures, dashboard reporting, and data pipelines to maintain pristine data hygiene.
AI Integration: Embed advanced AI tools into top-of-funnel and lifecycle motions, enabling automated account scoring, base enrichment, and intent signaling so outreach and routing are completely optimized.
Cross-Functional Collaboration and Project Management: Steer projects with internal partners such as Marketplace Operations, Finance, Product and Customer Success to represent GTM’s priorities and needs.
Planning & Performance: Redesign, model, and deploy fair, motivational commission structures tied to company objectives. Partner with Finance and pod leads on territory mapping, quota assignments, and capacity modeling.
Team Leadership: Build the S&O team roadmap. Manage, coach, and expand a high-performing RevOps team from the ground up, serving as the critical connective tissue across GTM, Marketing, Finance, and Product.
8+ years of experience in Business Operations with GTM experience, including Revenue Operations, Sales Operations, and GTM Strategy, with at least 3 years directly leading high-performance teams.
Proven leadership track record at a hyper-growth marketplace, SaaS, or workforce platform navigating the trajectory from $20M to $100M+ in revenue.
Advanced proficiency in Salesforce administration, data modeling, SQL, and business analytics dashboards (e.g., Metabase).
AI-native posture with direct experience utilizing predictive modeling or prompt-engineered tools (Claude, Clay, etc.) to streamline operational inefficiencies.
Collaborative, high-velocity, low-ego leadership style with excellent executive presence and written communication skills.
SQL and business analytics skills are non-negotiable.
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!
WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply.
Skills Required
- 8+ years in Business Operations with GTM experience, including Revenue Operations, Sales Operations, and GTM Strategy
- At least 3 years directly leading high-performance teams
- Proven leadership at a hyper-growth marketplace, SaaS, or workforce platform scaling revenue from ~$20M to $100M+
- Advanced proficiency in Salesforce administration
- Experience with GTM tech stack: Nooks, Gong, HighTouch, Clay
- Strong SQL skills (non-negotiable)
- Business analytics and data modeling skills; experience building dashboards (e.g., Metabase)
- Experience embedding AI tools for account scoring, base enrichment, intent signaling, or predictive modeling (e.g., Claude, prompt-engineered tools)
- Experience designing commission structures, territory mapping, quota assignments, and capacity modeling in partnership with Finance
- Collaborative, high-velocity, low-ego leadership style with strong executive presence and written communication
What the Team is Saying
WorkWhile Compensation & Benefits Highlights
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Healthcare Strength — Healthcare is presented as strong for corporate roles with 100% employer-paid employee medical, dental, and vision premiums and generous family coverage. Platform workers also have free telehealth access and, for eligible W‑2 roles, an ICHRA allowance toward individual coverage.
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Leave & Time Off Breadth — Time off is broad for corporate employees with unlimited PTO and other leave provisions. Platform W‑2 workers also accrue paid sick time at one hour per 30 hours worked.
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Parental & Family Support — Parental leave is presented as generous for corporate staff, with 16 weeks for birthing parents and 12 weeks for non‑birthing parents. Family support also includes an onsite Mother’s Room.
WorkWhile Insights
What We Do
WorkWhile is an AI-powered next generation labor platform that helps businesses in light industrial, hospitality, and events achieve over 90% fill rates and reduce no-shows through AI and predictive machine learning. We ensure seamless shift execution with trained, on-demand workers supported by on-site leads, real-time performance monitoring, and a robust accountability system. Our worker-first model boosts retention through benefits like next-day pay, telehealth, and free upskilling, while our platform delivers real-time analytics and dedicated support for every client. By combining flexibility, reliability, and deep insights, WorkWhile helps businesses scale efficiently and stay competitive.
Why Work With Us
WorkWhile is a technology platform with product and engineering at its core. Founded by alumni from Google, Meta, Yahoo, and Airbnb, continuous innovation is our strategy. We are an AI-native company that doesn’t just adopt new technologies, we operationalize them at scale to solve real business challenges.
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WorkWhile Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Our hybrid policy allows workers to work flexibly - either in person in one of our four hubs (San Francisco HQ, New York, Seattle, Toronto), or remote. We encourage employees coming in person to come 2-3x per week.
