Sr. IT Systems Engineer

Title: Sr. IT Systems Engineer Location: Remote

The Opportunity 🚀

Carrot is looking for a Sr. IT Systems Engineer to design, scale, and secure the identity, endpoint, and SaaS platforms that power our global, remote-first workforce. You will set the technical direction for how employees and devices connect to Carrot systems, while staying hands-on in the tooling, automation, and complex problem-solving that make IT reliable at scale.

This role sits at the center of IT engineering. You will lead larger initiatives from design through rollout, partner closely with Information Security on zero-trust and compliance priorities, and raise the bar for the rest of the team through standards, documentation, and mentorship. If you want broad technical ownership, influence over the IT roadmap, and the chance to build systems that grow with a high-growth healthcare company, this role was built for that.

What You’ll Own 💼

In this role, you will:

• Architect and own Carrot's identity, endpoint, and SaaS platforms, including Okta, JAMF, Intune, and Google Workspace, with a focus on security, reliability, and user experience
• Lead design and rollout of larger IT initiatives, such as zero-trust access models, device compliance frameworks, and global endpoint standards
• Build and maintain automation and infrastructure as code that manage configuration, provisioning, and lifecycle workflows at scale
• Partner with Information Security to design controls, drive vulnerability management, and keep Carrot audit-ready for SOC 2, HIPAA, and customer security reviews
• Serve as the senior technical escalation point, leading incident response and root cause analysis for complex or high-impact issues
• Define engineering standards, runbooks, and documentation, and mentor IT teammates to grow their technical depth
• Evaluate vendors and tools, build business cases, and make clear recommendations on build versus buy tradeoffs
• Design environments that support global care and operations teams, including secure and efficient remote computing setups
• Contribute to the IT roadmap and communicate priorities, risks, and progress to technical and business stakeholders

What Success Looks Like  📈

In your first 12–18 months, you will have:

• Established a clear, documented architecture and standards for identity, endpoint, and SaaS management that the team can build on
• Delivered at least one major platform initiative, such as a zero-trust access model or endpoint modernization, with measurable gains in security posture and employee experience
• Reduced manual IT work through automation and infrastructure as code, with a measurable drop in recurring ticket volume
• Strengthened audit readiness, contributing to clean results on security and compliance reviews
• Raised the technical capability of the team through mentorship, documentation, and shared standards
• Built trusted partnerships with Information Security, People, Engineering, and Finance

About You ✨

You likely have:

• 6+ years of experience in IT systems engineering, endpoint engineering, or infrastructure roles, including ownership of production platforms
• Deep, hands-on expertise with identity and access platforms such as Okta, including SSO, SCIM, lifecycle automation, and conditional access
• Expert-level experience managing Mac and Windows fleets with JAMF and Intune, including packaging, deployment, security policy, and compliance enforcement
• Strong scripting and automation skills (for example Python, Bash, or PowerShell), with experience using APIs and source-controlled configuration
• Experience designing and implementing security controls, such as encryption, vulnerability management, and zero-trust principles, in partnership with Security teams
• A track record of leading cross-functional technical projects from design through rollout without direct authority
• Experience mentoring or technically guiding other engineers
• Strong written and verbal communication skills, with the ability to translate complex tradeoffs for executive and non-technical audiences

Nice to Have ⭐

While not required, we would be especially excited if you bring:

• Experience in healthcare, health tech, or another regulated environment (for example, HIPAA or SOC 2)
• Experience with infrastructure as code and CI/CD practices applied to endpoint or SaaS configuration
• Hands-on experience with AWS or GCP and modern cloud networking concepts
• Experience designing remote computing environments for call center or clinical operations teams, such as VDI or managed browser models
• Experience building AI-assisted workflows or tooling to improve IT operations
• Relevant certifications (for example JAMF Certified Expert, Okta Certified Professional, or Microsoft Endpoint Administrator)

Why This Role Matters 🧡

Every Carrot employee depends on technology that is secure, reliable, and easy to use, whether they are supporting members through deeply personal care journeys or partnering with global employers. This role sets the technical foundation that makes that possible.

As Carrot continues to scale across geographies and functions, the architecture and standards you establish will protect member trust, strengthen our security posture, and give the business the speed and confidence to keep growing.

Why Candidates Join Carrot 🌍

Carrot offers the opportunity to do meaningful work in service of a deeply human mission.

Highlights include:

• A mission-driven company focused on expanding access to fertility and family-forming care globally.
• A high-growth environment where leaders are empowered to shape strategy and drive impact.
• Competitive compensation, equity, and comprehensive benefits.
• Flexible Time Off and a culture that actively encourages employees to recharge.
• Comprehensive parental leave and family-forming benefits.
• A collaborative, inclusive, and values-driven culture.
• The opportunity to work alongside passionate, thoughtful teammates committed to improving healthcare outcomes worldwide.

Compensation💰

Carrot offers a holistic Total Rewards package designed to support our employees in all aspects of their lives inside and outside of work, including health and wellness benefits, retirement savings plans, short- and long-term incentives, parental leave, family-forming assistance, and a competitive compensation package.

• Base Salary Range: $150,000 – $175,000 (primary range).
• Geo-Tier Adjustment: Up to $190,000 for highly experienced candidates within 50 miles of San Francisco, NYC, or Seattle.

Actual compensation may vary from the posted base salary depending on your confirmed job-related skills and experience.

A Note on AI

At Carrot, we believe AI can help us work smarter, move faster, and create more meaningful experiences for our members, customers, and each other. While not every role requires deep technical AI expertise, we value people who are curious, eager to learn, and excited to thoughtfully incorporate AI into their day-to-day work.

For some roles, AI fluency is a core requirement—and we'll call that out clearly in the qualifications. For everyone else, we're looking for people who embrace new ways of working, use AI responsibly to improve quality and efficiency, and continue to learn as the technology evolves.