Founding Product Manager - WorkHero

Company: Workshop Venture Partners
Location: Boston
Posted on: April 1, 2026

Job Description:

About WorkHero Tens of thousands of small HVAC contractors who keep our homes comfortable and enable the climate transition, are drowning in administrative work. Legacy software is clunky, full-time admins are expensive, and owners spend 20 hours per week on paperwork. WorkHero changes that. Our platform combines agentic AI with human-in-the-loop operations to autonomously handle back-office workflows like invoicing, permits, rebates, pricebooks, warranty registration and a whole lot more. Instead of asking contractors to learn new tools, our AI agents do the work , with expert office managers providing oversight and operational coaching. The result: real work gets done autonomously, helping small contractors grow profitable, resilient businesses while accelerating heat pump adoption nationwide. We've raised over $6.5M to date and are backed by Navitas Capital, Workshop Ventures, York IE, and strategic angels including a former ServiceTitan executive. Our advisors include Chad Laurans (Founder of SimpliSafe) and Gerald Chertavian (Founder of Year Up). The Role You'll be the first PM at WorkHero, working directly with the founders on the strategic decisions that shape the company. You'll lead discovery, design, and delivery across our product including the tools contractors use to run their businesses, the internal systems our dedicated Office Managers use to serve them, and the automation engine that ties it all together. This role blends user research, product strategy, and design. You'll spend real time with our customers, who are small business owners in the skilled trades. You'll then translate what you learn into mockups and product direction and collaborate closely with engineering to ship. If wearing many hats and operating with high autonomy sounds like your jam, keep reading. What You'll Do Deep User Discovery. Interview and shadow our operations team to understand their routines, workflows, and friction points. Interview and shadow contractors to understand their daily operations and unmet needs. Build real empathy for both sides and surface patterns across diverse businesses. Product Strategy and Solution Design. Synthesize user insights, operational context, and technical constraints into clear product opportunities. Identify strategic points of leverage. Study best-in-class tools (Field Service Management software, automation builders, AI assistants) and adapt what works to our domain. Rapid Prototyping. Use modern AI and design tools to quickly mock up concepts and gather user feedback. Mockups are often more effective than specs—you'll use them to align with engineering and validate ideas before committing resources. Collaboration and Delivery. Work closely with engineering to scope, plan, and ship. You're the bridge between users, operations, and the engineering team, ensuring shared context and efficient execution. Shape Product Vision. Use what you learn from discovery, usage data, and delivery to inform where we go next. Work directly with the co-founders on strategy and prioritization. Who We're Looking For We're looking for someone entrepreneurial, empathetic, and strategic—someone who wants to be the first PM at a fast-moving startup, working side-by-side with the founders to build something that matters. You've done zero-to-one product work. Whether your title was PM, product designer, founder, or something else, you've taken products from ambiguity through shipped features. You've operated in environments without a playbook. You're deeply empathetic and good at user research. You know how to run interviews that surface real insights. You can empathize and connect with blue collar workers and glean insights. You've observed users in their actual environment and translated that into product direction. You have design instincts. You don't need to be a trained designer, but you can look at an interface and know when something's off. You can rapidly prototype ideas using modern tools. You collaborate effectively with engineers. You know how to communicate product needs clearly—through mockups, conversation, and whatever format gets the team aligned. You don't hide behind documentation. You think strategically. You can zoom out to see the bigger picture and identify what matters most. You're not just executing, you're helping define what we should build and why. What Would Make You Exceptional Former founder or early employee at a startup Experience with contractors, small businesses, or home services Familiarity with FSM software (HouseCall Pro, ServiceTitan, Jobber) or the HVAC industry Experience building or shipping AI-powered products We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.

Keywords: Workshop Venture Partners, New Bedford , Founding Product Manager - WorkHero, IT / Software / Systems , Boston, Massachusetts