Headquarters: Remote
**About Carrot: **
Carrot is the leading global fertility and family care platform, built on intelligent care orchestration: the right clinical guidance, at the right moment, in the context of each member’s life. More than a thousand multinational employers, health plans, and health systems trust Carrot to support millions of members across 195 countries – from pre-pregnancy through menopause and major life moments in between. Carrot's comprehensive clinical program delivers industry-leading cost savings for plan sponsors and award-winning experiences and improved outcomes for millions of people worldwide.
Carrot is widely regarded as a defining force in healthcare innovation as a recipient of several top-tier awards, including Fast Company's 'Most Innovative Companies' and CNBC's '100 Barrier Breaking Startups'. The company is regularly cited by leading global outlets, including The Economist, Bloomberg, The Wall Street Journal, NPR, ABC News, and Harvard Business Review, as a leading voice on digital health, the future of work, and family health. Learn more at get-carrot.com.
**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: