Founding Sales Rep — Legal Tech SaaS | Ground Floor Go-To-Market Builder full time

Remote | $130k OTE | Early-Stage Role | Shape the Future of Medicaid Tech

Want to build a sales engine from the ground up — not just run someone else's playbook?

Join Medicaidsoft as one of the first sales hires and help modernize one of the most outdated and painful workflows in the US healthcare + legal system: long-term-care Medicaid applications.

We’ve built the TurboTax-for-Medicaid platform used by Medicaid consultants, elder law attorneys, and long-term-care facilities to simplify one of the most complex, paperwork-heavy processes in healthcare. The demand is real — and we're ready to scale.

This role is for a hungry, self-directed SaaS seller who wants:

✅ A seat at the table with the founder

✅ To build the outbound motion + sales playbook

✅ A product with real problem/solution fit in a huge, underserved space

✅ A chance to help shape GTM before the big growth wave hits

If you love early-stage building, ownership, and winning in messy markets… keep reading.

• Own full-cycle sales: prospect, run demos, close deals
• Sell into legal, healthcare, and long-term-care markets
• Partner directly with the founder on early deals & process
• Focus on regions where we're live (AZ, UT, MT, WI + expanding)
• Help build the GTM motion, sales assets, and repeatable playbook
• Use leads + CRM but also hunt creatively and self-source pipeline

You’ll also have support: a sales assistant + CS specialist who will own onboarding once you close the deal.

• 3+ years B2B SaaS closing experience
• Experience selling to law firms or healthcare orgs is a big plus
• Proven ability to generate pipeline in a startup with limited structure
• Consultative selling pro — strong discovery, problem-based selling
• Organized, proactive, gritty — you like figuring things out more than being handed the answers
• Collaborative, coachable, excited to build

• $60k base
• $130k OTE (uncapped commission)
• Remote-first team
• Real ownership in shaping the sales org + GTM function

There’s no 50-page onboarding manual.

No inbound pipeline waiting for you.

No big sales ops machine.

This is a ground-up build with a founder who wants a partner, not a passenger.

If you’re energized by that… you’ll thrive here.

Send a short note + your resume to: [email protected]

Tell us why early-stage building is your thing.