Regional Sales Executive
- Pay
- $300,000 – $325,000 per year
- Location
- Remote (US)
- Job type
- Full-time
- Level
- Senior
- Experience
- 3+ years
- Listed
- 23 days ago
Skills & highlights for this role
- enterprise sales to health systems
- pipeline management
- executive selling
- CRM
Also useful
- Salesforce
- revenue cycle knowledge
Stated benefits & perks
- Health
- Dental
- Vision
- 401k
- Flexible pto
About This Role
Reporting to the CRO, the Regional 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’re hiring across regions (East, Midwest/Central, West), with flexibility on location within those areas.
This is a hands-on, health system 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.
What You’ll Do
- 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.
Who You Are
- 3+ years of quota-carrying sales experience in healthcare IT or SaaS, with a track record of exceeding targets selling into health systems for at least 2 years.
- 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
Compensation
This role has a target total compensation range of $300,000 - $325,000 OTE
- Base salary: $150,000 - $175,000
Top performers have the opportunity to exceed OTE through uncapped earnings tied directly to performance.
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.
About Pivotal Health
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.
Why You’ll Love Working Here
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.
Equal opportunity and legal notices
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.
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.
From Pivotal Health's careers page, first listed on Rolev.ai on October 17, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
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Common questions
What is the salary for the Regional Sales Executive role at Pivotal Health?
The Regional Sales Executive posting at Pivotal Health states compensation of $300,000 – $325,000 per year. It is listed as a full-time position. Final pay may depend on location, experience, and interview evaluation on Pivotal Health's official career site.
Where is the Regional Sales Executive job at Pivotal Health located?
Yes, this Regional Sales Executive opening at Pivotal Health is listed as Remote (US). Always check Pivotal Health's application page for specific state eligibility or relocation policies.
What qualifications are required for Regional Sales Executive at Pivotal Health?
For the Regional Sales Executive role, Pivotal Health highlights 3+ years of relevant experience; experience with enterprise sales to health systems, pipeline management, executive selling, CRM. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.
How do I apply for the Regional Sales Executive position at Pivotal Health?
This listing links directly to Pivotal Health's Ashby application page. You can apply directly on Pivotal Health's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Ashby application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.