Head of GTM Strategy and Ops

WorkWhile Inc.

Job Overview

Location

San Francisco

Job Type

Full-time

Full Job Description

📋 Description

• Lead the design and evolution of WorkWhile’s multi-segment Go-To-Market (GTM) strategy, including intent signal capture, outbound sequence optimization, deal conversion levers, and pricing strategy.
• Own and manage the end-to-end GTM cadence, including weekly forecasting models, monthly business reviews, and quarterly business reviews (QBRs), delivering a single, methodology-backed forecast for leadership and investors.
• End-to-end ownership of the GTM tech stack including Salesforce, Nooks, Gong, HighTouch, and Clay, automating core pipeline architectures, dashboard reporting, and data pipelines to ensure pristine data hygiene.
• Embed advanced AI tools into top-of-funnel and lifecycle motions to enable automated account scoring, contact enrichment, and intent signaling, optimizing outreach and routing workflows.
• Collaborate cross-functionally with Marketplace Operations, Finance, Product, and Customer Success teams to align GTM priorities and drive execution of joint initiatives.
• Redesign, model, and deploy commission structures tied to company objectives, partnering with Finance and pod leads on territory mapping, quota assignments, and capacity modeling.
• Build, manage, and scale the Sales & Operations (S&O) team from the ground up, serving as the critical connective tissue between GTM, Marketing, Finance, and Product.
• Drive operational excellence by transitioning manual revenue processes into a scalable, automated revenue operating system that enables predictable, data-driven growth.
• Maintain and enhance business analytics dashboards to provide actionable insights for leadership decision-making and investor reporting.
• Leverage AI-native tools such as Claude and Clay to streamline operational inefficiencies and improve the accuracy and speed of GTM workflows.
• Ensure alignment between GTM strategy and company-wide objectives through consistent communication, performance tracking, and iterative process improvement.
• Lead initiatives to improve data quality and integrity across all GTM systems, ensuring reliable reporting and forecasting capabilities.
• Serve as the primary owner of revenue operations methodology, establishing standards and best practices across all GTM functions.
• Support scaling from $20M to $100M+ in revenue by refining GTM infrastructure, team structure, and operational workflows.
• Foster a high-performance, collaborative, and low-ego team culture focused on ownership, impact, and execution velocity.

🎯 Requirements

• 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

• 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

Skills & Technologies

Hybrid

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WorkWhile Inc.

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About WorkWhile Inc.

WorkWhile is a labor marketplace that uses predictive algorithms to match hourly workers with shifts offered by logistics, warehousing, hospitality, and retail employers across the United States. The platform vets applicants through background checks and skills assessments, then schedules them for shifts that fit their availability and pay preferences. Employers access a pool of pre-qualified workers on demand, while workers gain flexible hours, next-day pay, and benefits such as telemedicine and gas discounts. Founded in 2019, WorkWhile operates primarily in California and Texas, facilitating thousands of daily shift placements for both national brands and local businesses.

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