AI Automation Engineer

WorkHero is building the AI-powered back office for the skilled trades, starting with the $50B+ HVAC industry. We recently crossed $1M in ARR, closed $8M in seed funding, and are expanding our product and engineering organization. We're growing the team that turns the messy, undocumented workflows of small HVAC businesses into AI-powered automations that run on their own.

Tens of thousands of small HVAC contractors, the small business owners who keep our homes comfortable and install the heat pumps that enable our energy transition, are drowning in administrative work. Legacy software is clunky, full-time admins are expensive, and owner-operators spend 10+ hours per week on admin work.

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 independent contractors grow profitable, resilient businesses while accelerating heat pump adoption nationwide.

We've raised over $8M 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).

You'll sit between the contractors who own these businesses, our Senior Office Managers (SOMs) who run their back offices, and the engineers who build our platform — and for your accounts, you own the outcome. Your success isn't measured in automations shipped; it's measured in what changed for the contractor: hours back, invoices out faster, fewer things falling through cracks.

Learn how each business runs, then help shape what it becomes. Join onboarding calls, shadow SOMs, and sit with owners. Almost none of how these businesses operate is written down anywhere; it lives in someone's head and in the exceptions they've been making for years. You'll draw it out and make sense of it — but documenting the current state is only the start. The real work is partnering with the owner and SOM to imagine the ideal, AI-enabled version of the process, and turning that into a clear spec our system can act on.

Build the automations, then own them in production. Use our workflow builder, automation engine, and agentic tooling to ship automations that handle real work for real accounts. Then stay with them: watch the runs, catch the failures, figure out why a step broke on one account but not another. Build in the error handling, fallbacks, and checks that let a workflow survive a messy Monday, not just a clean demo. Write the specs, skills, and templates that make the system faster and smarter the next time around.

Find the patterns. We're moving from bespoke builds per account toward workflows that serve many businesses through configuration. Customization never goes away in this business; the goal is doing more of it, faster, with the same team. You'll spot what repeats across accounts, identify the dimensions of variation that make generalization possible, and bring what you learn in the field back to the roadmap. You’ll play an active role in shaping how our platform gets built.

Clear process thinking. You can take the tangled operations of small businesses, map them end to end, and find the structured processes hiding inside. You've done this before — through interviews, documentation, flowcharts — and used what you mapped to change how the work actually got done. Plenty of people can describe complexity accurately. We need someone who can resolve it into something simpler that works better.

Technical fluency. You stay close to the frontier of AI tooling, prompt LLMs effectively, and build with workflow tools like Zapier, Make, or n8n, AI coding tools, or your own scripts. You can read API docs and understand what's possible between two systems. You should understand what our platform can do, where the limits are, and when something ought to be possible but isn't yet. When you hit a wall, you should be able to bring a clear ask to an engineer, but you won’t need a software engineering background to succeed.

Comfort in front of customers. You'll lead discovery calls with owners and SOMs, ask the questions that surface how a business really works, and present what you've built. You don't need to be a closer, but people should walk away from a call with you feeling understood and confident their business is in good hands.

A high bar for quality. Small business owners trust us with their livelihoods. These automations touch invoices, payroll, and money moving between real people. You sweat the edge cases, check your work against reality, and treat a workflow as unfinished until it holds up on a bad day, not just a good one. You've made an automation reliable, not just functional: error handling, sensible fallbacks, and some way of knowing the output is actually right.

(Bonus) Trades / SMB industry experience. Experience in the trades or field service, hands-on familiarity with an FSM platform like HouseCall Pro, ServiceTitan, or Jobber, and/or familiarity with QuickBooks or small-business bookkeeping are accelerants for this role. Someone who already knows how an HVAC business runs has a head start on making an impact for our customers.

For decades, the software available to small contractors was built horizontally, designed to serve a dozen service businesses all at once. The result was that owners had to bend their workflows around the software, and most end up underutilizing the tool. Today we have an opportunity to build software that adapts to each contractor's business, and does far more of the work than ever before. That's the work of this role: identifying the core workflows of our customers and tailoring our solutions to meet them where they are.

If we get this right, thousands of small business owners across the trades get their nights and weekends back, build real wealth for their families, and compete on equal footing with private equity-backed conglomerates. Meanwhile, we build the productive capacity necessary to install millions of heat pumps and enable our energy transition.

This role can be a starting point for a dynamic career at WorkHero. As our product continues to advance, the reach of each automation engineer multiplies and the scope of our automations (and soon agents) will expand. If you demonstrate interest and aptitude, this is also a great launch pad for roles on our Product and Engineering teams.

Location: Remote, or hybrid in Cambridge, MA if you're local. The full team gets together in person several times a year.

Compensation: $100,000 to $130,000 base, plus meaningful equity.

Reports to: Co-founder

WorkHero is committed to building a diverse team. We encourage candidates from all backgrounds to apply.