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 partner and advisor for field-facing reps and managers regarding process execution, system navigation, and commission tracking.

• Process Redesign: Continuously audit sales processes to eliminate manual steps and friction, replacing legacy workflows with automated, AI-assisted solutions.

What We’re Looking For / Qualifications

• Experience: 5-8+ years of progressive experience in Revenue Operations, GTM Strategy, or Sales Operations at a fast-growing B2B SaaS or tech marketplace environment.

• AI Fluency & Tool Mastery: Deep hands-on experience leveraging modern AI/automation tools in a RevOps environment. Expert proficiency with Clay (waterfall enrichment, AI research agents, intent signaling), Nooks / Outreach, Gong (conversation intelligence), HighTouch (reverse ETL), and generative AI tools (ChatGPT/Claude/Custom GPTs) for operational workflows.

• Core RevOps Stack Expertise: Advanced Salesforce (SFDC) administration/architecture skills and expert Excel / Google Sheets financial and capacity modeling capabilities.

• Data & Analytics Capabilities: Proficiency in SQL, BigQuery, or Metabase/BI platforms for complex multi-data-source analysis.

• Strategic & Systems Thinking: Proven track record of taking messy, manual GTM processes and turning them into scalable, highly automated operating frameworks.

• Cross-Functional Leadership: Excellent communication and stakeholder management skills; comfortable challenging senior leadership with data-backed insights.

• Bias for Action & Ownership: High agency, entrepreneurial mindset, and comfort navigating ambiguity in a high-velocity, high-growth environment.

Benefits & Perks

• Hybrid work culture with office hubs in SF, NY, Seattle & Toronto

• In-person company offsites

• Medical, dental, & vision coverage

• Unlimited time off

• 401(k) with employer match

• WFH stipend to support your desk setup 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.