ABOUT HEALTHCARE.COM 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 • Experience in performance marketing, marketplaces, adtech, insurtech, health insurance, lead generation, or a similar environment • Experience working against 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 in your day to day work • Experience with BI and data platforms such as Sigma, Looker, Tableau, or Snowflake • Familiarity with health insurance distribution, lead generation, or call marketplaces 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 Bring your ideas. Bring your experience. Bring what makes you different. 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.

Program Manager, Marketplace Operations

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