GTM Engineer

ABOUT WORKWHILE WorkWhile is on a mission to help workers earn a better living and live better lives. More than 80 million Americans work hourly jobs, often with unpredictable schedules that pay close to minimum wage and offer limited benefits, leading to financial instability. 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. ABOUT THE ROLE We are seeking a strategic, AI-fluent, and results-oriented GTM Engineer to serve as a force multiplier for our go-to-market engine. Sitting at the intersection of GTM strategy, AI automation, and revenue architecture, you will lead the operational execution that powers our Sales, Account Management, and Sales Development teams. In this role, you won't just maintain systems; you will build and scale an automated revenue operating system. You will deploy AI tools and modern tech stacks to optimize pipeline generation, automate account enrichment, refine forecasting models, and eliminate operational friction across the full GTM funnel. Reporting directly to the President, you will act as a senior thought partner and tactical leader working cross-functionally with Sales, Marketing, Account Management, Finance, Data Science, and Product & Engineering. WHAT YOU’LL DO / KEY RESPONSIBILITIES 1. AI Integration & GTM Automation - AI-Native GTM Motions: Architect and scale AI-driven workflows across top-of-funnel and full lifecycle motions. Implement automated account scoring, dynamic buyer intent signal monitoring, and AI-assisted account enrichment (e.g., via Clay) to accelerate outbound execution. - Next-Gen Tech Stack Architecture: Own, optimize, and connect our best-in-class GTM tech stack, including Salesforce, Clay, Nooks, Gong, HighTouch, Outreach, and ZoomInfo, ensuring seamless data syncs and pipeline automation. - Prompt Engineering & Agentic Workflows: Leverage LLMs and generative AI tools to streamline operational workflows, auto-generate competitive and account intelligence briefs for field reps, and automate routine GTM administrative tasks. 2. Strategic Planning, Capacity & Territory Design - Planning & Modeling: Partner with leadership to drive annual/quarterly planning, capacity modeling, quota allocation, and territory design using predictive inputs. - Funnel Optimization: Analyze the end-to-end GTM funnel to identify conversion bottlenecks, sales cycle velocity levers, and ACV expansion opportunities. - Deal Desk & Compensation Strategy: Oversee deal structuring, custom quoting mechanics, and rules of engagement. Collaborate with Finance to administer, model, and optimize motivational incentive commission structures. 3. Advanced Analytics & Revenue Intelligence - Revenue Operating Cadence: Help run the end-to-end GTM business rhythm, delivering accurate weekly revenue forecasting, pipeline inspection, and performance diagnostics for executive leadership. - Dashboards & Data Infrastructure: Build advanced dashboards across Salesforce, Metabase, and BigQuery to provide real-time visibility into quota attainment, SDR pacing, account penetration, and win/loss diagnostics. - Data Hygiene & Pipelines: Maintain pristine GTM data hygiene by building automated validation pipelines and governance frameworks across all connected systems. 4. Enablement, Execution & Cross-Functional Leadership - Field Execution Support: Serve as the key operational…