Founding Account Executive

WorkHero•New York, NY

About The Position

WorkHero is building the AI-powered back office for the skilled trades, starting with HVAC — a $50B+ industry where tens of thousands of small contractors are buried in paperwork instead of doing the work they love. We just crossed $1M in ARR and have raised over $9M from 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). Our platform autonomously handles a range of back office tasks including invoicing, permits, rebates, and more — without asking contractors to learn new software. Our AI agents handle routine tasks while our expert humans act as a trusted layer to review work and build relationships. The result is fewer headaches, faster cashflow, and 20+ hours per week saved for these busy contractors. The Role We are hiring our first dedicated salesperson to work closely with the CEO and help build the sales function. This is a founding AE role. You will own deals end to end while helping shape how we sell. We already have strong inbound demand from ads, referrals, and events. In the first phase of this role, your pipeline will be primarily inbound (approximately 70–80%), and your focus will be converting that demand into revenue through fast, disciplined follow-up and a consultative, trust-first approach. Over time, you will also help test and build outbound, referrals, and other pipeline channels. You will sell to small HVAC business owners typically between 2 to 6 trucks. Success in this role requires being able to empathize, consult, and build trust with small business owners. This role is best suited for someone who is comfortable with ambiguity, enjoys building from scratch, and wants to help define the early sales motion.

Requirements

3 to 5+ years of sales experience with a strong track record of exceeding quota
Strong closing ability with experience managing and converting inbound demand
Experience leveraging AI tools in your workflows to drive real results
Experience selling to SMB owners, ideally inside a vertical SaaS company
Ability to build trust quickly with small business owners
Strong closer with excellent follow-up habits and objection handling skills
Experience with outbound - cold calls, email sequences, and creative prospecting
Comfortable working without a defined playbook and helping build one
Curious and able to quickly learn a new industry

Nice To Haves

Experience in HVAC, home services, or skilled trades
Familiarity with with field service software like ServiceTitan, Housecall Pro, or Jobber
Experience at an early-stage startup building a sales motion
Existing relationships in the trades ecosystem

Responsibilities

Own the full sales cycle from first conversation through close
Convert a high volume of inbound leads with speed, strong follow-up, and clear communication
Build trust with small business owners through a consultative approach
Use AI tools to improve prospecting, follow-up, and pipeline management
Test and develop outbound, referrals, and other pipeline channels
Document learnings including objections, messaging, and sales process
Partner with the CEO on pricing, positioning, and go-to-market strategy
Represent WorkHero at trade shows and other industry events
Help lay the foundation for future sales hires