About the role
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 and eat lunch together. When a deal needs something from product, you just walk over and ask.
Our founders are brothers - Jack (hi) runs GTM, Alex runs engineering. Our parents were lawyers. We started Ajax after we watched Alex's fiancée manually log billable hours and both agreed it was an insanely bad process.
I personally suck at selling things I don't believe in, and love selling things I do. One nice thing about building Ajax is that at least once a week, somebody says we've changed their life and refers a friend.
We work hard, we enjoy each other's company, we care about our customers, they can tell, and all of that helps us win - a lot. If you're a good AE, you'll hit quota and then some.
If you think selling it sounds fun, drop us a line!
Hiring process
- 30 minute screen with Jack
- 45-minute mock demo and debrief
- 3hr onsite and dinner with the team
- Offer
If this sounds like the right opportunity at the right time, reach out. If your background looks a little different than what I described, apply anyway - we care more about trajectory and hunger than checking boxes.
Jack Weinberger, Co-Founder, GTM