🚀 Founding Account Executive

About The Role

We're hiring a Founding Account Executive to build Readily's sales engine from the ground up. You'll work directly with the founders, owning the full sales cycle - from prospecting compliance leaders at health plans and hospitals to closing six-figure contracts. You'll have founder-level ownership, shaping how we sell, who we sell to, and what the playbook looks like for every rep who comes after you.

• Sit in on product calls.
• Fly to HCCA.
• Watch a CCO's face when they see what we built.

What You’ll Do

• Own the full sales cycle: prospecting → discovery → demo → negotiation → close.
• Build pipeline from scratch - outbound, conferences, founder intros, whatever works.
• Sell to compliance officers, VPs of Compliance, and CCOs at Medicare Advantage plans, Medicaid managed care organizations, and hospitals.
• Navigate complex, multi-stakeholder deals across compliance, legal, IT, and executive teams.
• Be the voice of the customer - feed product insights back to eng and shape what we build next.
• Develop the sales playbook, messaging, and processes that scale beyond you.
• Represent Readily at leading leading conferences and events.

What We’re Looking For

• 3-5+ years closing B2B SaaS deals, full-cycle.
• You've carried a quota and hit it.
• Hunger: High agency, a willingness to learn, and a drive to do whatever it takes.
• Consultative seller: You educate buyers, not just pitch them.
• Complex, multi-stakeholder sales cycles don't scare you.
• Customer-obsessed: You dig into the buyer's world. Unsolved customer problems keep you awake at night.
• Intellectually humble: Low ego, high curiosity, collaborative.
• Biased toward action: You act, you don't wait.

Experience

• Experience selling to healthcare organizations, health plans, hospitals, or buyers in regulated industries (compliance, GovTech, financial services, insurance).
• Familiarity with the healthcare regulatory landscape - CMS, OIG, HIPAA, risk adjustment, audit readiness.
• Existing relationships with compliance leaders at health plans or hospital systems.

Preferred Experience

• Specific knowledge of Medicare, Medicaid managed care, or FDR compliance.
• Certifications like CHC or HCISPP.
• Experience with MEDDIC, Challenger, or SPICED sales methodologies.

Compensation

• Base: $100K - $175K
• OPE: $120K - $150K (uncapped commissions)
• Equity: 0.20% - 1% (4-year vest, 1-year cliff)

Why Join Readily

• True founding-team ownership.
• Career-defining experience: ship products that rewrite how the industry works.
• Front-row to closing deals with billion-dollar enterprises.
• Hyper-growth environment (10× YoY - you’ll feel it).
• A real chance to fix healthcare’s most expensive problem with AI.
• Weekly pickleball 🏓 + a team that loves to win together. 📩