GTM Engineer

About WorkWhile
WorkWhile is on a mission to help workers earn a better living and live better lives. 83 million Americans work hourly jobs, often with unpredictable schedules that pay close to minimum wage and offer limited benefits, leading to financial instability.
WorkWhile identifies the best hourly workers and matches them with shifts that fit their skills, location, and life. 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

This role is the technical backbone of our go-to-market engine. You will sit at the intersection of Revenue Operations and GTM Engineering, responsible for designing, building, and maintaining the systems that power our growth.

You are a "hands-on builder" who thrives in the weeds of system administration but designs for long-term scale. Whether it’s fixing a complex Salesforce flow, optimizing our outreach sequences, or architecting a new AI-driven customer campaign, you own the technical execution that allows our GTM teams to move faster and smarter.

What you’ll do / Key Responsibilities

• Systems Administration & Optimization:

  • Own the technical health of our GTM stack, including Salesforce, Outreach, Nooks, and Gong.

  • Maintain a clean, well-documented data model across our stack to support accurate reporting, forecasting, and segmentation.

• Workflow Automation & Productivity:

  • Architect and deploy AI-powered workflows that translate GTM strategy into technical reality, like automating contracting or initial prospecting cadences.

  • Design and implement scalable automations that improve funnel conversion and eliminate manual work for sellers.

  • Lead the charge in making our GTM operations "AI-first". You will build and manage automated workflows using tools like Clay to accelerate prospecting and deal execution.

• Leadership & Influence

  • Act as the go-to technical expert across the org translating business requirements into robust system configurations.

  • Regularly present technical strategy, vision, and launches to leadership

  • Drive alignment across teams and hold stakeholders accountable to outcomes.

  • Build a culture of execution rigor, structured problem-solving, and continuous improvement.

What we’re looking for / About You / Qualifications

• 3-6 years of experience in GTM Systems, Revenue Operations, or GTM Engineering, or equivalent (marketplace or early-stage startup experience is a plus).

• Deep hands-on experience as an admin/developer for our core technical stack: Salesforce (Flows, Custom Objects), Outreach, Nooks, and Gong.

• Highly analytical and data-driven, skilled at architecting and deploying complex business workflows, and measuring business impact

• Proven ability to build in AI-native automation tools (like Clay) to drive GTM efficiency is a significant plus.

• Familiarity with HubSpot (specifically for marketing automation/operations) is a significant plus.

• Strong communication and influence skills, with the ability to synthesize insights and drive alignment across audiences from ICs to executives.

• Comfortable flexing between high-level strategy and hands-on execution, thriving in ambiguity.

• Intellectually curious with a strong bias for action and an entrepreneurial mindset.

• Passion for operational excellence, sales productivity, and creating business impact.

Benefits & Perks

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

• In-person company off-sites

• Medical, dental, & vision coverage

• Flexible time off

• 401(k) with employer match

• WFH stipend to support your home office needs

WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply. 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!