Build the GTM engine for the next generation of Healthcare AI
Location: Seattle preferred (Remote US considered)
About MySquireAI, Inc.
Healthcare operations still run on phone calls, faxes, payer portals, spreadsheets, and manual follow-up.
Every day, clinical and administrative teams spend countless hours scheduling patients, coordinating interpreters, chasing prior authorizations, following up on claims, and navigating fragmented systems.
We're building the AI execution layer for healthcare operations.
Our platform autonomously completes operational work across phone calls, portals, EHRs, messaging, and long-running workflows until the task is complete.
We're already helping healthcare organizations in the Seattle area, expanding across multiple workflows, and we're looking for our first dedicated sales leader to help build a repeatable enterprise GTM engine.
This is not a traditional Account Executive role.
- You won't inherit a territory.
- You won't receive a steady stream of inbound leads.
- You won't have SDRs booking meetings.
- You won't join an established sales organization.
- You will help build all of those.
If you're excited about creating the sales playbook rather than executing someone else's, keep reading.
What You'll Own
You'll work directly with the founders to build our enterprise sales motion from the ground up.
Your responsibilities will include:
- Building and executing our outbound strategy.
- Generating pipeline through outbound prospecting, referrals, partnerships, conferences, and creative GTM initiatives.
- Owning enterprise opportunities from first outreach through close.
- Helping define positioning, messaging, pricing, and sales collateral.
- Building repeatable qualification, forecasting, CRM, and pipeline management processes.
- Working closely with Product and Customer Success to expand existing customers into additional workflows.
- Becoming a trusted advisor to healthcare operators, executives, and practice leaders.
Minimum Qualifications Before You Apply
This role is designed for builders. Please apply only if at least SIX of the following are true (the last one is optional 😄).
- I joined a B2B SaaS startup at an early stage before it had 25 paying customers. I was one of the first three GTM or Sales hires at that company.
- In my previous role, I personally generated more than 60% of my pipeline through outbound prospecting, referrals, partnerships, or networking.
- I have personally sourced and closed at least five enterprise customers that I originated myself.
- I have worked directly with founders to define messaging, pricing, positioning, or GTM strategy.
- I consistently ranked in the top 20% of my sales team and have references.
- I want to help build a sales organization—not simply join one.
- Bonus (optional): You won't complain about Seattle weather nine months of the year.
Healthcare experience is a plus, but we care far more about your ability to build and scale an enterprise sales motion from the ground up. This is not an SDR or early-career sales role. We're looking for someone who has already built and closed enterprise sales motions at an early-stage B2B SaaS company.
What Success Looks Like
Within your first year, you'll help us:
Build a predictable outbound engine.
- Create a repeatable enterprise sales playbook.
- Win flagship healthcare customers.
- Expand existing customers into multi-workflow deployments.
- Lay the foundation for scaling the sales organization.
As the company grows, we expect this role to evolve into a leadership position responsible for building and leading our GTM organization.
Compensation
Base salary: $130,000–$170,000
Uncapped commission
Flexible paid time off
Remote-friendly work environment
Company-provided laptop and equipment
Application
Instead of a generic cover letter, please answer the following questions.
1. Tell us about one enterprise customer you personally hunted and closed.
Walk us through:
Why you targeted the account
How you secured the first meeting
How long the sales cycle took
The biggest obstacle you faced
Why you ultimately won
2. What is the earliest-stage startup you've joined?
Please include:
Approximate ARR or customer count when you joined
Approximate ARR or customer count when you left
Your specific contribution to that growth
3. Over the past two years, what percentage of your pipeline did you personally generate?
4. If you joined MySquireAI, Inc. next Monday, which five healthcare organizations would you pursue first?
Why those organizations?
How would you get the first meeting?
5. What is one GTM playbook or sales process that you built or materially improved?
Describe the problem, your approach, and the measurable outcome.
If reading this job description excites you more than it intimidates you, we'd love to hear from you.
Equal Opportunity Employer
MySquireAI, Inc. is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive workplace. Employment decisions are made without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other status protected by applicable law.
Work Authorization
Applicants must be authorized to work in the United States. We are not currently sponsoring employment visas for this position.
Confidentiality
Employment with MySquireAI, Inc. is contingent upon signing our standard Confidential Information and Invention Assignment Agreement (CIIAA).
