Founding Account Executive

Ajax uses AI to automate timekeeping for law firms. Customers love us - 14 of them have angel-invested their own money in Ajax, we win 97% of our pilots in a competitive market. We need a third AE to keep up with demand. You'll help build the GTM playbook and work directly with the Go-To-Market Co-Founder, Jack Location Mon-Fri in NYC HQ (we work best shoulder-to-shoulder) About Ajax Lawyers track their time in 6-minute increments. Lost billables cost them $100B a year. Ajax uses AI to automate timekeeping - we capture everything a lawyer works on and turn it into polished time entries. The result is that: Firms find revenue they didn't know they were missing The worst part of a lawyer's day gets 90% better Revenue has doubled roughly every quarter since March 2025. The role You'll build relationships with managing partners, run demos, and close. You'll also iterate on our sales process and help us break into new ICPs as we sell to bigger and bigger firms. Most of your deals will follow a 3-6 week cycle: a 30-minute demo where you walk a champion through Ajax, sometimes a follow-up call with decision-makers, then a proposal, negotiation, and close. The Activation team takes it from there - they run the pilot, train users, and build the ROI case. Some weeks you'll also: Work a conference booth, set meetings on the floor, and run follow-up the same night Fly out to present to a 150-person firm and win over 2 partners and a COO Sit with Jack after a tough call and figure out what you'd do differently next time Field a warm referral from a happy customer who just told their friend about Ajax Selling Ajax Lawyers poke holes in bad arguments for a living and aren't shy about calling bullshit. Winning them over looks like: Speaking their language, articulating the common pain points in words that resonate Taking a consultative approach so you don't lose deals to hidden objections Customer Love Customers say things like "you can take it from my cold, dead hands" and "I'm divorcing my husband for Ajax." A few proof points you'll have in your pocket: 30+ named case studies - firms recovering thousands per attorney per month in billable time they were leaving on the table An 18-0 record in head-to-head pilots against our closest competitors You heard that right - we have never lost a head-to-head pilot 15+ firms have switched from a competitor to Ajax; zero have gone the other way Word-of-mouth will do some of the job for you (see pic) - your job is to convert it into pilots. Who you are You've closed deals before - probably 1+ years of full-cycle or closing experience at an early-stage B2B startup. You're looking for a founding role where you can grow into midmarket sales, shape the playbook, and have a disproportionate impact on the trajectory of the company. You can hold a room with a managing partner. These are smart, skeptical people who run businesses. They'll push you on security, ask pointed questions about how the AI works, and test whether you actually understand their world. You need to be credible and composed. You can learn a technical product deeply enough to explain it. Ajax is a complex product that changes and improves constantly. You need to be curious enough to understand how it works and translate it into language a 50-year-old partner can understand. You want to build, not just execute. You'll shape the sales process, influence how we talk about the product, and have a real voice in where the company goes. Comp OTE : $190-270K (50% variable) Equity : Meaningful grant - this is a founding sales hire at a company with strong product-market fit and accelerating revenue Benefits : Medical, dental, vision, unlimited PTO, Wellhub, subway/bike fare for commutes, team dinner on Weds and free lunch Fridays, flexible hours, 4 WFH weeks / year Ramp : ramp plan so you can earn while you learn the product and the market What working at Ajax is like We're 14 people and we work in-office. GTM and engineering sit next to each other