Founding Account Executive

Readily; San Francisco (CA); On-site; USD 100,000 - 175,000; Full time

Job summary

Readily is hiring a Founding Account Executive to build the sales engine from the ground up. You’ll own the full sales cycle—from prospecting compliance leaders at health plans and hospitals to closing six-figure contracts—with founder-level ownership.

You’ll write the playbook, shape who we sell to, and influence how the team scales. Expect high visibility and a direct channel to the founders in a fast-growing AI-driven healthcare compliance startup.

Qualifications

• 3–5+ years closing B2B SaaS deals.
• Quota carrying and meeting targets.
• Educates buyers, not just pitches.
• Ability to navigate complex multi-stakeholder sales cycles.
• Bias toward action and ownership of outcomes.

Responsibilities

• Own the full sales cycle: prospecting → discovery → demo → negotiation → close.
• Build pipeline from scratch via outbound, conferences, founder intros.
• Sell to compliance officers, VPs of Compliance, and CCOs at health plans, hospitals.
• Navigate multi-stakeholder deals across compliance, legal, IT, and exec teams.
• Be the voice of the customer; feed product insights back to eng.
• Develop the sales playbook and scalable processes.
• Represent Readily at leading conferences and events.

Skills

Closing B2B SaaS

Consultative selling

Customer obsession

High agency

Multi-stakeholder deals

Job description

About Readily

30% of U.S. healthcare cost is

30% of U.S. healthcare cost is administration. We're fixing that. Readily is building the compliance layer for the healthcare industry. Billion-dollar healthcare organizations turn to Readily to analyze regulations, conduct audits, and automate compliance readiness with AI. We're the fastest-growing company in this space - 10x revenue YoY. And we're just getting started. There's an old Yorkshire saying: "Where there's muck, there's brass." Healthcare compliance is messy. But in that mess lies an enormous opportunity. If you're hungry to take ownership and build systems that matter, this is it.

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. 10x impact vs big tech sales.

No SDR team. No inbound safety net. No playbook handed to you - you'll write it.

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.

Strongly Preferred

• 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.

Nice to Have

• 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
• OTE: $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 (10x 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.