Enterprise Account Executive

Cara AI · Remote · Full-Time

The Role

Cara AI is an early-stage health tech company building AI-powered infrastructure for in-home assessments serving health plans, Medicaid managed care organizations, and hospital systems. We have deployed product, real metrics, and a pipeline of named enterprise prospects. We need a closer.

This is a full-cycle enterprise sales role. You own everything from prospecting through signed pilot agreement. There is no SDR layer, no inherited territory, and no playbook handed to you. The founder handles contracting once you close. You build the rest.

In addition to enterprise sales, you will own our D2C user acquisition effort driving outreach to reach 1,000 consumer users (caregivers and family members of aging adults). D2C traction directly supports enterprise sales narrative and payer pilot conversations.

What You’ll Do

• Own the full sales cycle — prospecting, discovery, demo, procurement navigation, and signed pilot agreement
• Build enterprise pipeline from scratch across health plans, Medicaid MCOs, and hospital systems
• Develop and advance relationships with clinical ops, SDOH, vendor management, and population health leaders
• Translate regulatory and operational pain points — risk adjustment, HCBS quality reporting, care tier placement — into compelling business cases
• Represent Cara at industry conferences including RISE, NAMD, and AHIP
• Work directly with the founder on deal strategy, pricing, and prospect-specific positioning

What We’re Looking For

• 5+ years enterprise health IT sales with closed deals involving health plans or Medicaid MCOs
• Demonstrated history of building pipeline from scratch — not inheriting a territory or working inbound leads
• Fluency in Medicaid managed care, LTSS, SDOH, or post-acute landscape
• Comfort with 90–120 day sales cycles and multi-stakeholder procurement processes
• Experience running cold outreach campaigns — email, LinkedIn, or direct — at volume
• Commission-motivated; equity upside at an early-stage company matters to you
• Can operate independently with minimal support infrastructure

Not a Fit If

• You need a large SDR team or warm inbound to generate pipeline
• You require a mature sales playbook or established brand recognition to close
• You are uncomfortable with early-stage product gaps and iterating in real time with customers

Compensation

Competitive base salary commensurate with experience, plus uncapped commission on closed pilots and a D2C milestone bonus. Meaningful early-stage equity with a 4-year vest and 1-year cliff. Specific figures shared during the interview process.