Head of GTM Strategy and Ops

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.

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.

• 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.