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.
The Opportunity
As our Program Manager, Marketplace Operations, you’ll sit at the center of our Marketplace business, owning a portfolio of initiatives that span Analytics, Engineering, Marketing, Data Science, Sales, and partner facing teams.
You’ll bring structure and visibility to multiple workstreams, connect dependencies across teams, and make sure priorities turn into action. This isn’t a role where you simply collect updates and maintain timelines. You’ll dig into the data, verify progress, identify what needs attention, and help keep teams accountable to their commitments.
Timing matters in our business. Medicare AEP opens October 15 and ACA OEP opens November 1. You’ll work backward from critical deadlines, anticipate risks and dependencies, and help keep the portfolio moving.
Where You’ll Make an Impact
• Own the Marketplace Operations project portfolio from planning through execution and handoff
• Manage multiple concurrent workstreams across Analytics, Engineering, Marketing, Data Science, Sales, and partner facing teams
• Run the operating cadence for the portfolio and provide clear, executive ready status updates
• Maintain a single source of truth for initiatives, owners, milestones, dependencies, decisions, and deadlines
• Use data, dashboards, and SQL to independently validate project status rather than relying solely on reported updates
• Identify cross functional dependencies and surface risks before they impact critical deadlines
• Build alignment and hold owners accountable across teams you don’t directly manage
• Maintain clear decision and change documentation across initiatives
• Communicate risks early and bring options for moving forward
• Transition completed initiatives to day to day business owners with clear ownership, monitoring, and follow through
• Use AI agents, workflow automation, and other tools to make portfolio management smarter and more efficient
What You'll Bring to the Team
• 4 to 8 years of experience managing complex, cross functional projects or programs in a metrics driven environment
• Proven ability to manage multiple projects or workstreams simultaneously
• Working SQL knowledge with the ability to write basic queries and independently verify data
• Fluency with performance KPIs including CPA, conversion rate, ROAS, pacing, and margin
• A track record of driving alignment and accountability across teams without direct authority
• Strong executive communication skills with the ability to communicate clearly and concisely
• The confidence to surface risks and deliver difficult news early, along with options for moving forward
• A strong sense of ownership and the ability to identify what needs attention without waiting to be told
What Sets You Apart
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
- 4 to 8 years of experience managing complex, cross-functional projects or programs in a metrics-driven environment
- Experience managing multiple projects or workstreams simultaneously
- Working SQL knowledge, including the ability to write basic queries and independently verify data
- Fluency with performance KPIs including CPA, conversion rate, ROAS, pacing, and margin
- Experience driving alignment and accountability across teams without direct authority
- Strong executive communication skills
- Ability to surface risks early and provide options for moving forward
- Strong ownership and ability to identify priorities independently
- Experience in performance marketing, marketplaces, adtech, insurtech, health insurance, lead generation, or a similar environment
- Experience with immovable seasonal deadlines, major launches, enrollment periods, or peak business cycles
- Experience with Jira administration or workflow design
- Hands-on experience using AI tools, LLM agents, or workflow automation
- Experience with BI and data platforms such as Sigma, Looker, Tableau, or Snowflake
- Familiarity with health insurance distribution, lead generation, or call marketplaces
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.


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