AI Automation Engineer

WorkHero•New York, NY

3h•$100,000 - $130,000•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. 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: ability to take tangled operations, map them end to end, and find structured processes.
Experience mapping processes through interviews, documentation, and flowcharts to change how work gets done.
Technical fluency: staying close to AI tooling, effective prompt LLMs, and experience with workflow tools like Zapier, Make, or n8n, AI coding tools, or own scripts.
Ability to read API docs and understand system integrations.
Understanding of the platform's capabilities and limitations.
Comfort in front of customers: leading discovery calls, asking questions to understand business operations, and presenting work.
A high bar for quality: sweating edge cases, checking work against reality, and ensuring automations are reliable with error handling and sensible fallbacks.

Nice To Haves

Trades / SMB industry experience.
Hands-on familiarity with an FSM platform like HouseCall Pro, ServiceTitan, or Jobber.
Familiarity with QuickBooks or small-business bookkeeping.

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 undocumented business processes.
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 using our workflow builder, automation engine, and agentic tooling.
Own automations in production: watch the runs, catch failures, and figure out why a step broke on one account but not another.
Build in error handling, fallbacks, and checks that let a workflow survive a messy Monday.
Write the specs, skills, and templates that make the system faster and smarter the next time around.
Spot patterns across accounts to move towards workflows that serve many businesses through configuration.
Identify dimensions of variation that make generalization possible.
Bring learnings from the field back to the roadmap and play an active role in shaping how our platform gets built.