Build something that actually matters.
We're a small team with a big problem to solve. The 97% of care that happens between clinical visits is invisible to the healthcare system — and it's killing people. If you want to work somewhere your quota actually translates to lives changed, read on.
Open Positions
1 open role · Remote-first
Head of Enterprise Sales
Actively HiringHealth SaaS & Payer Solutions
We are looking for a mission-driven enterprise sales leader who knows how to navigate the health plan and provider landscape. You will own the full sales cycle — from identifying target accounts to closing deals with Medicaid MCOs, Medicare Advantage plans, and health systems. Target enterprise contracts are $10M+ ARR. This is an uncapped commission-plus-equity role at the ground floor of a company with the right product at the right moment in the market.
About the Opportunity
OutsideINsights is at an inflection point. We have a validated product, a clear market opportunity in the move toward value-based care, and the right timing as CMS accelerates quality-weighted reimbursement through Stars, HEDIS, and V28 risk adjustment. Target enterprise contracts with Medicaid MCOs and Medicare Advantage plans represent $10M+ ARR opportunities — and the first rep in the door sets the commission structure for everyone who follows. This role has uncapped commission and meaningful equity — the kind of deal that rewards people who get in early and execute.
What You'll Do
- Own end-to-end enterprise sales pipeline for health plan and provider segments
- Build and maintain relationships with VPs and C-suite at Medicaid MCOs, Medicare Advantage plans, and behavioral health organizations
- Lead discovery, demo, and proposal processes tailored to payer economics (MLR reduction, Stars ratings, HEDIS compliance)
- Collaborate with the founder on go-to-market strategy and account prioritization
- Develop sales materials, pitch decks, and ROI models specific to payer and provider audiences
- Represent CodePause at industry conferences and health plan networking events
- Provide market feedback to inform product roadmap and positioning
What You Bring
- 5+ years of enterprise SaaS sales experience, with at least 3 years in health plan, managed care, or value-based care markets
- Demonstrated track record of closing 6-figure+ SaaS contracts with health plans, MCOs, or large health systems
- Deep understanding of payer economics: MLR, Stars ratings, HEDIS measures, risk adjustment, and value-based care contracts
- Experience selling to VP/C-suite buyers in regulated healthcare environments
- Ability to navigate long enterprise sales cycles with multiple stakeholders
- Familiarity with HIPAA compliance requirements and healthcare data sensitivity
Nice to Have
- Experience with care management, remote patient monitoring, or population health platforms
- Existing network within Medicaid MCO or Medicare Advantage markets
- Understanding of post-discharge care documentation workflows and Transitional Care Management (TCM) billing requirements
- Knowledge of FHIR/EHR interoperability landscape
Why CodePause
Ground-floor opportunity
Join before the institutional funding round and shape how we go to market.
Clear ICP, proven problem
The 97% between-visit gap is documented, validated, and costly. The pitch practically writes itself.
Mission that matters
Every deal you close prevents avoidable hospitalizations and supports families who are already doing their best.
Founder access
Work directly with a founder who has lived the problem from both clinical and family sides.
Send your resume and a brief note on why this role resonates with you. We read every application personally.
Apply for This RoleDon't see your role listed?
We're always interested in meeting people who believe that families should be partners in care — not bystanders. If you're passionate about closing the gap between clinical visits, reach out.
Send a General InquiryEqual Opportunity Employer. CodePause Inc. is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other characteristic protected by applicable federal, state, or local law.
Pay Transparency (New York State Pay Transparency Law, effective September 17, 2023). The anticipated on-target earnings (OTE) for this position are $500,000–$1,000,000+ per year, consisting of performance-based commission (minimum 5% of closed ARR) plus equity incentives. There is no guaranteed base salary. Target enterprise contracts represent $10M+ ARR per engagement; final compensation is determined by individual performance, deal structure, and additional incentive terms established at time of engagement. CodePause Inc. complies with applicable state and local pay transparency laws.
Work Authorization. Applicants must be authorized to work in the United States. CodePause Inc. does not sponsor employment visas at this time.
Reporting Structure. This role reports directly to the Founder & CEO.