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Open role · Sales

Account Executive, Enterprise

ShareWillow is the AI-native performance and operating system for the 4 million people who run the trades. We help technicians make more money, get paid instantly, and finish jobs faster with less callbacks. We help companies create incentives for their technicians that reward performance instead of hours worked. Our customers see an average of 20% increase in profit within the first year through increased average ticket, billable efficiency, and less callbacks.

ShareWillow is hiring an Enterprise AE and you'll play a huge part in rapidly expanding our growth and helping our companies in the trades fundamentally improve their businesses. As an Enterprise Account Executive, you will help identify, engage, and close new business from strategic enterprise customers including large home service companies, franchises, and private equity-backed holding companies.

This is a role for world-class sales hunters: people who have a proven track record of closing 7-8 figure deals, immediately see where we win, and want to build a generational $10 billion company.

Must be okay with getting pinged on Slack in the evenings and weekends. We are not constrained by a typical 9-5 schedule. We want to win.

Who you are

You have high integrity and a proven track record of winning.

  • 3+ years of Enterprise SaaS sales, consistently closing 7-8 figure deals
  • Proven success selling into large companies, franchise groups, and PE-backed holding companies
  • Strong technical fluency: comfortable doing live and virtual product demos, discussing integrations, API/workflow mapping, and partnering with technical stakeholders
  • A true hunter mentality: evidence of consistent self-sourced pipeline generation and strong outbound muscle
  • Operates with grit, speed, and obsession: you thrive in high-growth, high-intensity environments
  • Highly coachable, curious, and competitive
  • Exceptional written and verbal communication skills and you're able to lead rooms of senior executives and command attention
  • You have high integrity and will walk away from a sale before you jeopardize integrity

What you’ll do

Run the full enterprise cycle.

  • Run the full Enterprise cycle: outbound prospecting, multi-stakeholder discovery, tailored demos, ROI modeling, negotiations, and closing
  • Sell directly to C-Suite, VPs, Directors, and operational leaders across field-heavy enterprises and franchise groups
  • Lead multi-threaded, complex sales cycles with cross-functional support (solutions, product, engineering, and customer success)
  • Develop deep expertise in various trades (HVAC, plumbing, electrical, pest control, etc) and bring market intelligence back to the team
  • Build playbooks and repeatable processes as one of the first Enterprise AEs
  • Forecast with precision while managing dozens of active opportunities
  • Establish ShareWillow as the category leader in every industry in the trades
  • Follow up relentlessly and keep a clean, accurate pipeline in HubSpot
  • Tell customer stories and outcomes to enterprise prospects and show them how they can achieve those outcomes

You might not be a fit if…

An honest filter. We’d rather you know now.

  • You want a mature sales org with SDR support
  • You only want to work warm inbound leads
  • You dislike cold calling or manual prospecting
  • You need a lot of structure before taking action
  • You are looking for a low-intensity sales role
  • You aren't competitive and you want to coast on a high base salary

Why join

Get in early. Win big.

This is a chance to be the first enterprise sales hire at an early-stage company with proven product-market fit. You'll work directly with the founder, talk to customers constantly, close real revenue, and shape the sales culture. You'll work on a small, talented team of relentless winners to build a $10 billion company.

You'll have unusually high upside: $300K OTE, uncapped commission, 100% medical and dental benefits, 401k with employer match, and meaningful early-stage equity.

We're proud to be an equal opportunity employer open to all qualified applicants regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital or familial status, disability, pregnancy, gender identity or expression, veteran status, genetic information, or any other legally protected status.