Pivot Health, a subsidiary of HealthCare, Inc., is a high-growth health insurance distribution company specializing in Short-Term Medical (STM), Fixed Indemnity, and ancillary health products. We operate in a dynamic, start-up-oriented environment and are expanding rapidly as market conditions — including ACA subsidy changes and a projected 9–10 million individual market exits — create significant demand for our product portfolio.
About The Role
The VP, Sales & Account Management is a newly created, senior leadership role that will own and drive all broker sales and account management activity for Pivot Health. Reporting directly to the President, this executive will build and lead a high-performance team, establish new business development discipline, and deepen relationships across our broker and consultant distribution channels. This is a hands-on leadership role for someone who thrives in a fast-paced environment, can operate both strategically and tactically, and is ready to make an immediate impact.
What You'll Do
Sales Leadership & Revenue Growth
- Own the broker and consultant distribution sales strategy, with accountability for revenue targets across non-owned channels
- Transition the sales organization from a reactive account management model to a proactive hunter/farmer structure
- Recruit, onboard, and scale new broker and FMO relationships to expand Pivot's active distribution footprint
- Drive new business development with independent agents, general agents, and field marketing organizations (FMOs)
- Represent Pivot Health at industry events, carrier partner meetings, and key broker/consultant forums
Account Management & Retention
- Lead and develop the Account Management team, ensuring existing broker relationships are nurtured, productive, and growing
- Establish SLAs, performance metrics, and accountability frameworks for the AM team
- Partner with internal operations and member services to resolve broker escalations and improve the end-to-end broker experience
- Develop and execute a tiered broker engagement model (key account vs. general book)
Team Building & Culture
- Hire, coach, and develop a team of BDMs and Account Managers; establish clear roles, comp structures, and performance expectations
- Create a winning team culture grounded in accountability, collaboration, and results
- Work cross-functionally with marketing, operations, and product to align distribution strategy with company priorities
Strategy & Reporting
- Contribute to the company's Growth Roadmap and quarterly operating plan (Rocks) as a key member of the leadership team
- Provide regular pipeline, forecast, and performance reporting to the President
- Identify market trends, competitive dynamics, and channel opportunities to inform product and pricing decisions
Who You Are
- 10+ years of progressive sales and account management experience in the health insurance distribution space
- Deep, established relationships with brokers, general agents, and/or consultants in the individual and small group health market
- Demonstrated success building and leading sales teams in a growth-stage or entrepreneurial environment
- Track record of hitting and exceeding revenue targets in a quota-carrying or team leadership capacity
- Strong understanding of the U65 / non-ACA insurance market, distribution economics, and broker compensation structures
- Self-starter with the ability to hit the ground running — comfortable operating without a fully built infrastructure
- Excellent communicator, collaborator, and relationship builder across internal and external stakeholders
Preferred / Strong Plus
- Experience with Short-Term Medical (STM) products and distribution
- Background in ancillary health products: dental, vision, accident, critical illness, or fixed indemnity
- Familiarity with FMO/IMO recruiting and management
- Experience managing or transitioning TPA/carrier partner relationships
- Prior work in a start-up, scale-up, or private equity-backed health business
Skills Required
- 10+ years of progressive sales and account management experience in the health insurance distribution space
- Deep, established relationships with brokers, general agents, and/or consultants in the individual and small group health market
- Proven success building and leading sales teams in a growth-stage or entrepreneurial environment
- Track record of hitting and exceeding revenue targets in a quota-carrying or team leadership role
- Strong understanding of the U65 / non-ACA insurance market, distribution economics, and broker compensation structures
- Self-starter able to operate without fully built infrastructure
- Excellent communication, collaboration, and relationship-building skills
- Experience with Short-Term Medical (STM) products and distribution
- Background in ancillary health products (dental, vision, accident, critical illness, or fixed indemnity)
- Familiarity with FMO/IMO recruiting and management
- Experience managing or transitioning TPA/carrier partner relationships
- Prior work in a start-up, scale-up, or private equity-backed health business
HealthCare.com Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about HealthCare.com and has not been reviewed or approved by HealthCare.com.
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Healthcare Strength — Medical, dental, and vision coverage with HSA options are consistently listed across company and third-party profiles, with some postings citing employer HSA contributions. Health coverage appears to be a reliable pillar of the package.
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Retirement Support — A 401(k) plan with company match is highlighted in postings and benefits summaries, including references to a “fantastic 401k.” Retirement offerings are viewed as a strong component of total rewards.
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Leave & Time Off Breadth — PTO, paid holidays, bereavement, extended leave, and parental/family leave appear across listings, with some roles specifying roughly 15–20 days of PTO. Time-off breadth reads as competitive within a modern, remote-friendly package.
HealthCare.com Insights
What We Do
HealthCare.com is a healthcare technology company focused on making healthcare simpler, more accessible and easier to navigate. We combine technology, data and deep industry expertise to help consumers make more confident decisions about their health and coverage. Under the HealthCare.com umbrella, our businesses serve consumers across different parts of their healthcare journey. Our Marketplace helps people search, compare and find health insurance options that fit their needs. Pivot Health provides flexible health insurance solutions designed for people whose needs don’t always fit a traditional model. TrustRx extends our reach into pharmacy, helping us create an even more connected healthcare experience. While our businesses solve different problems, we share one goal: take experiences that are traditionally complicated and make them easier for the people who rely on them. That mission shapes how we work, too. We’re a team of builders, problem solvers and healthcare experts who move quickly, challenge conventional thinking and believe great ideas can come from anywhere. With employees across the U.S. and around the world, collaboration, ownership and different perspectives are part of how we operate. HealthCare.com has been building in healthcare since 2014, backed by investors with experience building some of the world’s leading internet companies. Today, we’re continuing to evolve beyond where we started, bringing together technology, insurance and pharmacy to build smarter, simpler ways for consumers to navigate healthcare.
Why Work With Us
Our people are at the heart of everything we build. Across 25 states and six countries, we’re a collaborative, curious team that values fresh ideas, transparency and ownership. We move fast, think big and give people the flexibility and support to do meaningful work, grow their careers and enjoy life outside of work.
