Founding Account Executive

ABOUT CARESWIFT

CareSwift uses AI to automate ambulance reports. Paramedics spend 30% of their shift on paperwork — we're cutting that to zero. We're a Y Combinator-backed startup (S25) based in New York City, and we're growing fast. You'll be the one turning that story into signed agencies across the country.

THE TEAM

Brian is a former EMT who saw firsthand how much time paramedics waste on paperwork — he started CareSwift to give them back hours of their day. We're a small, tight-knit founding team that moves fast and cares deeply about the EMS community.

ABOUT THE ROLE

Until now, every CareSwift deal has been sourced, run, and closed by our founder. As our Founding Account Executive, you'll take over the full sales cycle — prospecting, discovery, demos, pilots, procurement, and signature — and turn what's working into a repeatable playbook.

This is not a book-meetings-and-hand-off role. You'll own revenue: a pipeline you build, deals you run, and contracts you close. You'll work side by side with Brian every day, and as we grow, you'll have the first shot at building and leading the sales team.

THE DEALS YOU'LL RUN

• Who buys: Agency chiefs and operations directors — plus the medical directors, boards, and municipal stakeholders standing behind them.
• The motion: Outbound-driven. Demo → pilot → contract, working within each agency's existing ePCR and QA workflow.
• Deal size & cycle: You'll work deals ranging from ~$10K/year with smaller agencies to $800K/year contracts with large systems. Most close in about a month; the largest move through municipal procurement cycles.

WHAT YOU'LL DO

• Own the full cycle. Prospect, qualify, demo, pilot, negotiate, close. From first cold call to signed contract, the deal is yours.
• Prospect & research: Identify high-potential EMS agencies, ambulance services, and fire departments. Build and maintain your own pipeline — no SDR is feeding you meetings yet.
• Run demos that land: Tailor every demo to the agency in front of you — their call volume, 911/IFT mix, ePCR setup, QA process, and billing workflow.
• Navigate real-world EMS buying: Chiefs, boards, budget cycles, municipal procurement, the occasional RFP. You'll drive multi-stakeholder deals all the way to signature.
• Close and hand off: Negotiate pricing and terms, get contracts signed, and transition new customers cleanly to onboarding — then stay close for expansion and referrals.
• Build the playbook: Track what's working, keep the CRM clean, and turn your wins into repeatable sequences, talk tracks, and objection handling for the reps who come after you.
• Be the voice of the customer: What you hear in the field shapes our product, pricing, and roadmap.

YOUR FIRST 90 DAYS

• Days 1–30: Learn the product cold and the workflows it replaces. Shadow live demos, sit in on pilot check-ins, and map how EMS agencies actually buy — who signs, who champions, who blocks. Start building your own pipeline.
• Days 31–60: Take the wheel. Run demos end to end, manage active pilots, and close your first deals. Start documenting the motion: which messaging lands, which objections repeat, where deals stall.
• Days 61–90: Own the number. Carry a full pipeline against a quota, run a repeatable full-cycle motion, and feed what you're hearing back into product and positioning.

WHO YOU ARE

• You know EMS. You've worked in or around emergency medical services — as a provider, dispatcher, administrator, or vendor selling into EMS. You speak the language, know the pain points, and can hold your own with a chief.
• You've closed business. You've owned a number and taken B2B deals across the line — SaaS, medical equipment, or selling into public safety or government all count. You're comfortable running pilots, working multiple stakeholders, and surviving procurement. A polished enterprise-SaaS resume isn't required; having closed real deals is.
• You're a full-cycle hunter. You source your own pipeline, and you'd rather build it yourself than wait for it.
• You sell by listening. You diagnose before you pitch, and you're honest when we're not the right fit — the EMS world is small, and reputation compounds.
• You're self-driven. Early-stage means ambiguity, ownership, and no playbook until you write it.
• You're organized and persistent. Clean CRM, relentless follow-up, never annoying.

COMPENSATION & BENEFITS

• On-target earnings: $180,000–$225,000 (base + variable)
• Base salary: $120,000–$130,000
• Equity: 0.25%–0.5%
• Benefits: Health insurance, 401(k), and more

LOCATION

In-person in New York City, with a remote day bank allowing a set number of remote days per year.

WHY JOIN CARESWIFT

• Ground floor, real ceiling. You're our first sales hire. Perform, and you're the obvious pick to build and lead the sales org.
• Real impact. Your customers are the people who save lives — you're giving them hours of their day back.
• Y Combinator backed. The resources, mentorship, and network of the world's top startup accelerator behind you.

TO APPLY

Tell us about your connection to EMS, the deal you're proudest of closing — what it took, start to finish — and why an early-stage startup excites you. Resumes are great, but we care more about your story.