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VP, Sales & Account Management

September 8, 2026

Join Us!

HealthCare.com has become one of America’s fastest-growing insurtech companies, revolutionizing how consumers shop for health insurance. Leveraging advanced technology and data science, the company has developed customized proprietary products to better fit consumer requirements, enhance customer satisfaction, and take some of the guesswork and inefficiencies out of buying insurance.

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

Benefits

Opportunity to work from home
Excellent work environment
Medical, dental, and vision insurance
Up to 15 days of paid time off
11 company observed holidays
8 weeks of paid parental leave
401k plan with company match
Life insurance
Professional growth opportunity
Most importantly, an inclusive company culture established by an incredible team!

Get to Know Us!

linkedin.com/company/healthcare-com

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...