Healthcare.com is a healthcare technology company building smarter ways to connect people and partners with the coverage, care, and solutions they need.
We’re three businesses, one company. Through Marketplace, Pivot Health, and TrustRx, our work spans health insurance marketplaces, flexible health coverage, and pharmacy, giving us more ways to solve meaningful problems across the healthcare ecosystem.
Healthcare doesn’t stand still, and neither do we. We’re curious, collaborative, and always looking for better ways to solve problems, use technology, and make an impact.
About The Role
Senior operating leader for Healthcare.com’s consumer acquisition business. This is a business ownership role, not simply a functional marketing role. The VP will own day-to-day performance across first-party and third-party acquisition, with accountability for revenue, contribution margin, ROAS, volume, and strategic growth. The role will manage forecasting and capital allocation, develop channel leaders, incubate new growth opportunities, improve measurement and conversion signals, and build a faster, more precise, AI-enabled operating model. The VP will also work closely with Marketplace Ops and the Distributor team to align consumer supply, acquisition budgets, partner demand, and shared performance goals.
Who You Are
• Senior leadership experience in performance marketing, growth, or digital acquisition
• Direct ownership of substantial budgets, multi-channel portfolios, and financial results
• Strong command of revenue, contribution margin, ROAS, CAC/CPA, LTV, and volume
• Deep understanding of first-party and third-party acquisition channels
• Exceptional analytical instincts and willingness to get hands-on
• Track record of managing managers and building accountable teams
• Strong forecasting, measurement, attribution, conversion-signal, and MarTech/AdTech experience
• AI-enabled mindset, curiosity, and willingness to lead an AI-enabled operating transformation
What Sets You Apart
• Hands-on experience using AI, coding agents, or automation to build useful capabilities
• Experience in a regulated or compliance-intensive industry
• Experience with digital marketplaces, comparison shopping, lead generation, or insurance distribution
• Experience incubating and scaling new acquisition channels
Why Healthcare.com
We’re building a company for people who want to be part of what’s changing, not watching it happen. Here, you’ll have the opportunity to take on meaningful challenges, share new ideas, and make an impact you can see.
The Good Stuff- Medical coverage with PPO and HSA plan options
- Company funded HSA contributions from $2,000 to $4,000 annually
- Dental and vision coverage
- 401(k) with company match and eligibility from day one
- Paid time off and company holidays
- Paid parental and pregnancy disability leave
- Company paid life and AD&D insurance
- Employee Assistance Program (EAP)
- Employee discounts on travel, entertainment, fitness, dining, and more
We’ll give you the opportunity to make it matter.
Healthcare.com is an equal opportunity employer. We value different backgrounds, experiences, and perspectives and are committed to creating an inclusive workplace where everyone has the opportunity to thrive.
Skills Required
- Senior leadership experience in performance marketing, growth, or digital acquisition
- Direct ownership of substantial budgets, multi-channel portfolios, and financial results
- Strong command of revenue, contribution margin, ROAS, CAC or CPA, LTV, and volume metrics
- Deep understanding of first-party and third-party acquisition channels
- Exceptional analytical skills and willingness to work hands-on
- Experience managing managers and building accountable teams
- Experience with forecasting, measurement, attribution, conversion signals, MarTech, and AdTech
- AI-enabled mindset and willingness to lead an AI-enabled operating transformation
- Hands-on experience using AI, coding agents, or automation to build useful capabilities
- Experience in a regulated or compliance-intensive industry
- Experience with digital marketplaces, comparison shopping, lead generation, or insurance distribution
- Experience incubating and scaling new acquisition channels
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.
