AI Automation Engineer

Summary

WorkHero is building an AI-powered back office for skilled-trades businesses, beginning with the HVAC industry. The AI Automation Engineer will understand customer operations, design and build AI-enabled workflows, own automations in production, and identify repeatable patterns to improve the platform.

Responsibilities

• 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

Skills

• 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
• 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
• Location: Remote, or hybrid in Cambridge, MA if you're local
• 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

Qualifications

Must Haves

• 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
• 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
• Location: Remote, or hybrid in Cambridge, MA if you're local

Nice to Haves

• 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

Benefits

• Meaningful equity
• Remote work, or hybrid work in Cambridge, MA if local
• A launch pad for roles on the Product and Engineering teams for candidates who demonstrate interest and aptitude