Head of GTM Strategy and Ops
San Francisco, CA · HybridFull-timePosted 3mo agoStill listed 3 days ago
Most applications go out cold — see where you stand first. No sign-up to start.
Watch jobs like this. New roles like this one near San Francisco, CA, by email.
Don't just apply. Show up ready.
Olive works from this exact posting.
At a glance
Olive lists jobs from US employers, including remote roles you can work from the United States.
Job overview
WorkWhile is hiring a Head of GTM Strategy and Ops. The Head of GTM Strategy & Operations will lead WorkWhile's multi-segment Go-To-Market (GTM) machine, transitioning revenue operations from manual processes to an automated, data-driven system. This role involves driving strategy for GTM motion enablement, owning the end-to-end GTM cadence, and managing the GTM tech stack. The Head will also integrate advanced AI tools, collaborate cross-functionally, and redesign commission structures. They will build and coach a high-performing RevOps team.
Key focus areas include Drive strategy for GTM motion enablement and evolution projects, Own and manage the end-to-end GTM cadence, and Deliver a single, methodology-backed forecast for leadership and investors.
Successful candidates bring 8+ Years Business Operations Experience, 3+ Years Team Leadership, and Hyper‑Growth Marketplace Experience. Important skills include GTM Strategy, Revenue Operations, Sales Operations, Salesforce Administration, Data Modeling, and SQL. Preferred (not required): Metabase, Claude, Clay, and Nooks.
Skills & qualifications
Skills
Qualifications
Benefits
Full job 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.
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.
About You
-
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.
Similar jobs, posted recently
Open roles like this one, listed in the last 30 days.
Chief of Staff to Head of Engagement ManagementMercor · San Francisco, CA · $180–230K/yrPosted 2w agoPosted 2w ago
Senior Manager, GTM Growth StrategySalesforce · San Francisco, CA · $150–227K/yrPosted 2 days agoPosted 2 days agoSenior Manager, Marketing Strategy & OperationsLyft · San Francisco, CA (Hybrid) · $132–165K/yrPosted 1w agoPosted 1w ago
- Pricing Strategy, Manager/Senior ManagerSalesforce · San Francisco, CA · $123–227K/yrPosted 1w agoPosted 1w ago
- Customer Strategy & Planning Director, Agentforce OperationsSalesforce · Remote · US · $164–262K/yrPosted 1w agoPosted 1w ago
You've read the whole posting — now see how you match it.