This is a cutting edge, get-your-hands-dirty opportunity to help build a GTM department from the ground up.
Aspen AI is an AI communication platform for the legal industry. Our AI “employees” talk to leads and clients by phone, text, and email, and run the workflows law firms use to acquire, convert, and manage clients.
Our founders have closed every deal to date, which means our CEO is running the engineering team while also making sales calls, speaking at conferences, and unearthing a wide variety of other business opportunities. That's the biggest constraint on our growth, and you're the hire who removes it.
You will not inherit a team, a pipeline, an SDR, or a playbook. You will build the lists, send the outreach, run the calls, work the conference floors, close the business yourself, and track every lead so meticulously that nothing slips.
What You’ll Own
- Customer Lifecycles: Grow Aspen AI to 80 law firm customers in 12 months — pipeline, discovery tracking, demo, negotiation, close, onboarding.
- The Machine: Own the CRM as a system of record and build the qualification criteria, stages, sequences, demo, and forecast a future team can run.
- Outreach: You will build the list of leads yourself; researching the accounts, writing the emails, booking the meetings, logging the activity, following up.
- The Pitch: Make the product obvious to a managing partner who's never used an AI tool, then make the case in their numbers — cost per signed case, intake conversion, staffing cost.
- Customer Qualifications: Disqualify poor‑fit firms, set expectations, document what was promised, and hand off to the onboarding team cleanly. You own the accuracy of what they inherit and partner with them on expansion.
- Customer Needs: Know how many AI Employees they need, how we can adapt to their systems and culture, and how to plan for their success.
- Negotiations: Diligently keep every deal moving through negotiation and close, and know when to elevate rather than improvise.
- Product Feedback: Bring what firms actually need back to the product team.
- Conferences: Research and recommend the events, own the logistics, work the floor and booth yourself, and do the follow‑up.
Requirements
- You've carried a real revenue target and can speak specifically to your pipeline, success rate, and deal sizes.
- You've built pipeline from nothing, personally and recently. Cold outreach is a skill you still have, not one you used to have.
- At least one prior role selling software or a comparable technology product to a business buyer.
- Exceptional composure on a call, in writing, and in person. You can explain a technical product to a non‑technical buyer, speak plainly with engineers, and know how to listen to them and alleviate their concerns.
- You can learn a complex product deeply enough to demo it accurately.
- You are meticulous and organized. The CRM is your lifeline.
- Willing to travel, and comfortable running an event on your own.
Preferred
- Existing relationships with PI and Mass Tort law firm owners, attorneys, or the vendors who sell to them.
- Experience selling into personal injury, mass tort, or other contingency‑fee firms.
- Legal tech or legal services background — case management, intake, records retrieval, lien resolution, litigation finance, legal marketing.
- First or second commercial hire somewhere, or a sales process built from zero.
Not a Fit If
- You want to start by hiring and managing a team.
- You’re not ready to roll up your sleeves.
- You need SDRs, inbound, or partners to generate most of your pipeline.
- You consider list building, CRM hygiene, booth logistics, or a fifth follow‑up a job to be delegated.
Disclaimer: This is an exceptionally rigorous, intense and time‑consuming role, not a traditional 9-to-5. One week you may present Aspen AI at a major legal conference and negotiate with a large firm; the same week you may write cold emails, update the CRM, and coordinate booth materials. No task is beneath you, no detail is too small, and no obstacle is a reason to lose progress. If you want to build the commercial foundation for autonomous AI in the legal industry, we'd love to hear from you.