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 Junior IT Systems Specialist is a part-time, on-site intern role providing hands-on technical support to staff located at the Pharmacy. This position serves as a first point of contact for routine technology issues and helps keep daily business operations running without interruption.
Day-to-day work spans desktop and hardware support, user account administration, printer and peripheral troubleshooting, and equipment setup. This is a fast-paced, people-facing role well suited for someone who enjoys practical problem-solving and wants to build a strong foundation in enterprise IT support.
What You'll Do- Desktop & OS Support: Troubleshoot and resolve routine Windows desktop and operating system issues.
- Hardware Setup & Repair: Assemble, configure, deploy, and repair desktop workstations, laptops, printers, mobile devices, and peripherals; diagnose hardware faults and coordinate repairs or replacements as needed.
- Software Installation: Image and install operating systems, productivity applications, drivers, and routine security updates.
- User Account Management: Handle Active Directory tasks, including creating new user accounts, resetting passwords, clearing account lockouts, and managing basic system access.
- Printer Support: Install and maintain printers, resolving driver, print queue, and connectivity issues.
- Cable Management & Workspace Standards: Perform cable management and keep workstation and equipment areas organized, labeled, and standards-compliant.
- Ticket & Request Handling: Respond to walk-up and ticketed support requests, prioritizing and following through to resolution.
- Escalation: Recognize complex or unresolved issues and escalate them to senior IT staff with clear, complete details.
- Documentation & Inventory: Record work performed and solutions accurately and keep asset and inventory tracking sheets up to date.
- General IT Operations: Assist with other day-to-day IT operations and projects as assigned.
- You have basic knowledge of troubleshooting common technology issues.
- You have customer service experience and are comfortable helping people solve problems.
- You have personal or professional experience working with Windows computers.
- You're organized, dependable, and able to follow through on support requests.
- You're comfortable asking questions and escalating issues when something is outside your level of expertise.
- You enjoy hands-on work and are interested in building your technical skills in a real-world IT environment.
These aren't required, but they're a plus:
- Currently or previously enrolled in a higher education program related to Information Technology or a similar field.
- Experience working with Active Directory.
- IT certifications such as the Google IT Support Professional Certificate or CompTIA A+.
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
- Basic knowledge of troubleshooting common technology issues
- Customer service experience and comfort helping people solve problems
- Personal or professional experience working with Windows computers
- Organized, dependable, and able to follow through on support requests
- Comfort asking questions and escalating issues beyond current expertise
- Interest in hands-on work and building technical skills
- Currently or previously enrolled in higher education related to Information Technology or a similar field
- Experience working with Active Directory
- Google IT Support Professional Certificate or CompTIA A+ certification
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.
