Senior IT Support Engineer

Pomelo Care is the leading virtual medical practice for women and children, providing care across pregnancy, postpartum, pediatrics, menopause, and perimenopause. We combine proactive, 24/7 clinical care with technology that helps us reach patients earlier, identify risks sooner, and deliver personalized care throughout their journey. Our team includes clinicians, technologists, operators, and problem-solvers working together to make high-quality care more accessible for families nationwide.

About The Role

Your North Star: Build an IT foundation that keeps Pomelo secure, supported, and ready to grow.

As our Senior IT Support Engineer, you’ll help shape how IT works at a rapidly scaling virtual medical practice, taking ownership of core systems, solving our toughest support challenges, and making onboarding and offboarding faster and more reliable. This is a hands-on role for someone who sees what needs to improve and carries it through. The systems you strengthen and the repetitive work you automate will help Pomelo spend more time on work that advances care.

This role reports to the IT Manager and is open to any candidates located in the continental US.

What You’ll Do

As a senior member of a growing IT team, you will help build a world-class IT program at a rapidly scaling, high-growth startup. You'll be the person the team turns to when something is broken, unclear, or doesn't have an owner yet. Specifically you will:

• Create an intuitive and user-friendly technology environment for your fellow Pomelos!

• Own IT support coverage during east coast hours for a team that's mostly remote, with folks working from our NYC and SF offices too

• Be the escalation point for the hard problems: tricky device, identity, and access issues that need real troubleshooting, not a runbook

• Own our core systems end to end, including Okta, Google Workspace, Slack, and our MDM, and make changes to them confidently and safely

• Build and run onboarding and offboarding for a distributed team, and keep making it faster and less manual: provisioning accounts, shipping devices, and recovering them when people leave

• Design and implement security policies across Okta, Slack, Google Workspace and others to keep our patients' data safe, and partner with security and compliance on audits

• Find the repetitive work and automate it away with Okta Workflows, Slack Workflows, and scripting

• Raise the bar for the rest of the IT team by writing clear documentation, setting good process, and helping newer teammates level up

Who You Are

• 5+ years of experience in IT support/operations, including time as the go-to person for escalations or as the owner of core systems

• A track record of getting things done: you see a problem, figure out the right fix, and ship it without needing to be chased

• Deep experience administering Okta, Google Workspace, and Slack, including SSO, SCIM provisioning, group and policy design, and access reviews

• Deep experience supporting Apple hardware with MDM tools like Iru (formerly Kandji) or Jamf, and running device lifecycle for a remote workforce

• Comfort scripting or automating (Okta Workflows, Bash, Python, Google Apps Script, or similar)

• Strong customer service and communication skills — you focus on end-user experience, empathize with users, and can explain technical tradeoffs to non-technical people

• Good judgment working independently — you'll anchor coverage for the front half of the day and make calls without waiting for someone to sign off

Compensation

The expected base salary range offered for this role is $115,000 - $130,000. This role is also eligible for equity, giving you an ownership stake in Pomelo’s mission. Actual compensation may vary based on relevant experience, skills, competencies, and certifications.

Benefits and Perks

By joining Pomelo, you’ll get in on the ground floor of a fast-moving, well-funded startup on a mission to improve outcomes for all mothers and babies. We cultivate a collaborative, patient-first environment where data drives our decisions and team members are challenged to learn, grow, and have fun together. We also offer:

• Comprehensive Health, Dental, and Vision coverage for employees and their families

• High deductible Health Plans with Health Savings Account (HSA) options

• Flexible Spending Account (FSA)

• Equity grant participation

• 401(k) program

• Competitive vacation policy

• 16 weeks paid parental leave

• Fully remote work flexibility (within the US) with offices in NYC and SF for those who prefer in-person work

We are committed to hiring the best team to improve outcomes for all mothers and babies. To solve the complex challenges facing the diverse population we serve, we need diverse perspectives, actively welcoming people of all races, ages, sexual orientations, gender identities and expressions, national origins, religions, disabilities, and veteran statuses. We strive to cultivate an inclusive and respectful environment where team members thrive by working across disciplines, moving fast, making data driven decisions, learning continuously, and always putting the patient first.