H

HealthCare

Guiding Medicare choices and health coverage

VP – Sales & Account Management

Full-Time
No salary listed
Expert
Remote in USA
Remote
Sales & Account ManagementAccount Executive, Account Management

About the job

Requirements
  • 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.
  • A track record of hitting and exceeding revenue targets in a quota-carrying or team leadership capacity.
  • A strong understanding of the U65 / non-ACA insurance market, distribution economics, and broker compensation structures.
  • The ability to operate independently and effectively without a fully built infrastructure.
  • The ability to communicate, collaborate, and build relationships across internal and external stakeholders.
Responsibilities
  • 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 field marketing organization relationships to expand Pivot Health's active distribution footprint.
  • Drive new business development with independent agents, general agents, and field marketing organizations.
  • Represent Pivot Health at industry events, carrier partner meetings, and key broker and consultant forums.
  • Lead and develop the Account Management team, ensuring existing broker relationships are nurtured, productive, and growing.
  • Establish service-level agreements, performance metrics, and accountability frameworks for the Account Management 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 for key accounts and the general book.
  • Hire, coach, and develop a team of business development managers and Account Managers; establish clear roles, compensation structures, and performance expectations.
  • Create a team culture grounded in accountability, collaboration, and results.
  • Work cross-functionally with marketing, operations, and product to align distribution strategy with company priorities.
  • Contribute to the company's Growth Roadmap and quarterly operating plan 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.
Desired Qualifications
  • Experience with Short-Term Medical products and distribution.
  • A background in ancillary health products, including dental, vision, accident, critical illness, or fixed indemnity.
  • Familiarity with field marketing organization and independent marketing organization recruiting and management.
  • Experience managing or transitioning third-party administrator and carrier partner relationships.
  • Prior work in a start-up, scale-up, or private equity-backed health business.

About the company

Healthcare.com is a digital platform that helps individuals, families, and LGBTQ+ people choose health coverage and make informed healthcare decisions. It works by providing guidance during the Medicare Annual Enrollment Period (AEP) and offering tools and research to compare plans, assess coverage, and understand costs. The platform also addresses discrimination in health insurance and offers resources about medical debt and its impact on credit scores. Revenue comes from selling healthcare products, offering research tools, and guiding users through the AEP process. Its approach centers on user-friendly services, inclusivity, and financial health, aiming to make healthcare decisions easier and more accessible for a diverse audience.

Company Size

201-500

Company Stage

Series C

Total Funding

$243.8M

Headquarters

Miami, Florida

Founded

2014

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Simplify Jobs

Simplify's Take

What believers are saying

  • Healthcare.com's July 8, 2025 Medicare updates show rapid product adaptation to CMS changes.
  • Autopilot pilot results across two enrollment periods support broader partner adoption in 2025.
  • Five million-plus users create recurring AEP traffic and cross-sell opportunities across coverage lines.

What critics are saying

  • CMS 2026 Medicare and marketplace rules tighten oversight, squeezing conversion and compliance.
  • Autopilot depends on distributor demand; carriers can internalize bidding and bypass Healthcare.com.
  • Medicare Annual Enrollment concentrates revenue; a broken AEP economics cycle threatens existential failure.

What makes HealthCare unique

  • Healthcare.com launched Autopilot on March 26, 2025, using 100M data points.
  • Autopilot spans Medicare Advantage, Medigap, ACA, and under-65 insurance verticals.
  • The company owns consumer-intent data, not just lead-gen inventory, strengthening pricing power.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Life Insurance
  • 401(k) Retirement Plan
  • 401(k) Company Match
  • Paid Vacation
  • Paid Holidays
  • Parental Leave
  • Remote Work Options
  • Professional Development Budget

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

-1%

2 year growth

-1%
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