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.

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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