AI Automation Engineer

WorkHero•New York, NY

2d•Remote

About The Position

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. About WorkHero 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).

Requirements

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.
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.
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.
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.

Nice To Haves

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.

Responsibilities

Learn how each business runs, then help shape what it becomes. Join onboarding calls, shadow SOMs, and sit with owners.
Draw out and make sense of how businesses operate, document the current state, and partner 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.
Stay with automations in production: 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.
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.
Play an active role in shaping how our platform gets built.