Enterprise Sales Executive (Midwest)

Pivotal Health is the leading technology platform that helps healthcare providers get paid fairly in an increasingly complex reimbursement landscape.

Today, many providers face persistent underpayment from health insurance companies, despite delivering high-quality care. While processes like IDR (Independent Dispute Resolution) were designed to promote fairness, they’re often administrative-heavy, time-consuming, and difficult to navigate without the right tools.

Pivotal Health combines software, data, and service into a seamlessly integrated, AI-driven platform that simplifies these complex reimbursement workflows. We help providers efficiently dispute underpaid claims, reduce administrative burden, and recover the reimbursement they’re entitled to; without adding more work to already stretched teams.

Our full-service IDR solution is just the starting point. We’re building solutions that enable providers to operate with clarity, control, and confidence across the reimbursement journey.

Reporting to the CRO, the Enterprise Sales Executive is responsible for driving new business with hospitals and health systems. This role focuses on building executive relationships, progressing complex opportunities, and closing high-quality contracts.

We are specifically hiring within the Midwest to strengthen our presence and coverage in the region. Candidates should be located in the Midwest, though exact location within the region is flexible.

This is a hands-on, health system Enterprise sales role. You’ll be selling into Finance and Revenue Cycle leadership, as well as running consultative, multi-stakeholder deals, and helping expand our presence within health systems. We’re looking for someone who consistently performs at a high level and knows how to generate and close opportunities in a complex market.

• Generate pipeline: Build new relationships with health system CFOs, Revenue Cycle, and Finance leadership.
  

• Own complex sales cycles: Progress opportunities from initial outreach through close, managing multiple stakeholders, timelines, and deal requirements.
  

• Develop account strategy: Own account planning, identify decision-makers and champions, and align deals to customer priorities, budget, and ROI.
  

• Partner on deal execution: Work closely with the CRO on negotiations, contracting (including redlines), and closing.
  

• Maintain executive relationships: Build credibility with senior stakeholders and position yourself as a trusted partner.
  

• Drive pipeline discipline: Maintain accurate pipeline tracking, forecasting, and CRM hygiene (Salesforce is our source of truth).
  

• Support customer transition: Partner with Customer Success to ensure smooth onboarding, implementation, and identify expansion opportunities.
  

• Improve the motion: Bring ideas to reduce sales cycle time and improve how we engage and win with health systems.
  

• 7+ years of quota-carrying sales experience in healthcare IT or SaaS, with a track record of exceeding targets selling into health systems

• Strong understanding of the acute care environment, including Revenue Cycle, Finance, and operational workflows

• Proven ability to generate pipeline and close net new business in complex, multi-threaded sales cycles

• Experience selling to executive stakeholders (CFO, SVP/CRO Revenue Cycle, VP Finance) and translating solutions into financial and operational impact

• Strong executive presence with the ability to build credibility and drive deal progression

• Highly organized with strong pipeline management, forecasting discipline, and experience working within a CRM (e.g. Salesforce)

• Comfortable operating in an early-stage, fast-moving environment with a high degree of ownership

This role has a target total compensation range of $350,000 – $400,000 OTE

• Base salary: $180,000 – $200,000

Top performers have the opportunity to exceed OTE through uncapped earnings tied directly to performance.

We’re a collaborative, low-ego team on a mission to make healthcare reimbursement fairer for providers. While we primarily hire around our core hubs–Los Angeles and New York–we remain open to exceptional talent outside those regions. Remote and hybrid flexibility varies by role and team, and is outlined in each job description.

If you’re excited by solving complex problems and making a real-world impact, we’d love to hear from you.

Benefits Include:

• Competitive compensation, including equity

• Full health, dental, and vision coverage

• Retirement savings plan through 401(k)

• Flexible time off

• Opportunities for company-wide connection and events

Ready to Make an Impact?
We’re building something meaningful; and we want you on the team.

Bring your ideas, curiosity, and drive, and let’s transform healthcare reimbursement together.

Work Authorization

Candidates must be authorized to work in the United States without current or future employer sponsorship.

Equal Employment Opportunity

Pivotal Health is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, color, religion, sex, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected status.

Reasonable Accommodations

Pivotal Health provides reasonable accommodations for qualified individuals with disabilities in accordance with applicable laws. If you need assistance during the application or interview process, please let us know.

Background Checks

Employment is contingent upon successful completion of applicable background checks, where permitted by law.

At-Will Employment

Employment with Pivotal Health is at-will and may be terminated by either party at any time, with or without cause or notice, in accordance with applicable law.