Director of Engineering, Infrastructure

We're building the cloud infrastructure and delivery platform that one of healthcare's most ambitious technology transformations runs on, and we need an Engineering Director to own the Infrastructure behind it all. This is a player-coach role where you'll lead strategy and stay hands-on in the work alongside a small, focused team, reporting directly to the CTO.

This role is about infrastructure and developer enablement. As our AI strategy evolves, we see a world where many outside of traditional engineering and data roles will contribute to our technology ecosystem. We believe reliability, security, and cost discipline come from good platform design and automation, and that ticket queues and runbooks are signs we haven't solved the underlying problem. You'll bring a clear point of view on what a modern, AI-native infrastructure org should look like, the judgment and technical skill to make it real, and the leadership instincts to build and develop the contributors around you.

In this role you will:

• Own cloud infrastructure end-to-end across our cloud environments, staying hands-on with IaC, CI/CD, and observability alongside the team
• Own the SDLC surface area (dev environments, lower envs, release mechanics, monitoring and response) so engineers can ship in minutes rather than days
• Build the substrate that lets AI agents observe, reason, and act on business systems with safe defaults, and the rails that let AI-assisted apps from people outside of tech be deployed and supported without becoming operational liabilities
• Participate in security operations alongside our SecOps team on CSPM, threat management, and patch management as the infrastructure-side owner of remediations
• Frame infrastructure decisions in terms of business outcomes (operational efficiency, financial impact, clinical results), and make progress and tradeoffs visible to leadership as a natural byproduct of how you work
• Lead and develop a small, high-impact team, and operate as a peer to our SecOps, Data, IT Systems, and App Engineering leaders as a unifying technical force across the org

You should get in touch if:

• You have an engineering background with deep, hands-on experience operating production infrastructure across at least two major clouds (GCP, AWS, Azure) and with modern infrastructure-as-code (Terraform or similar)
• You have built and operated modern CI/CD systems, dev environments, and observability stacks. What you've shipped matters more than the size of the fleet you've managed.
• You've built and operated infrastructure across different company sizes and business contexts. Cross-domain breadth is a real asset; experience in regulated domains (healthcare, financial services) is helpful but not required
• You hold a strong, well-reasoned point of view on platform philosophy, and can defend when to standardize, when to give teams room, and how to make the safe path the easy path
• You have shipped AI-native operational systems. That might be AI agents that triage alerts, draft RCAs, manage cost, or execute runbooks, or frameworks that let non-traditional contributors (junior engineers, analysts, AI agents, vibe-coders) ship safely.
• You're action-oriented on governance and security participation. You document what matters, automate what you can, and don't let process become a bottleneck
• You have built and developed teams. You think about composition intentionally, hire for gaps, and invest in people's growth
• You're a strong communicator: clear, direct, and concise with both technical and non-technical audiences

Success in this role looks like

• First 90 Days: Develop a clear point of view on the current state of the infrastructure, CI/CD, and operational tooling. Identify the highest-leverage opportunities. Ship a first step-function improvement or eliminate a fundamental operational limitation.
• 6 Months: AI-assisted operations are in place for alert triage and incident response. CI/CD and dev environment strategy are coherent across the org. The small team operates in a new operating model with substantially higher leverage per engineer.
• Long Term: Infrastructure is a quiet enabler. Engineers, AI agents, and non-tech contributors ship safely and quickly without the platform being the bottleneck. Cloud cost is managed as an engineering discipline. The team is growing skills, increasing capacity, and operating with autonomy.

We're hiring across multiple teams at Clover and Counterpart Health— our recruiting team will assess your background and connect you with the best-fit opportunity. You'll learn more about the specific team and interview process as you move through the process.

Benefits Overview: 

• Financial Well-Being: Our commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, we offer a performance-based bonus program, 401k matching, and regular compensation reviews to recognize and reward exceptional contributions.
• Physical Well-Being: We prioritize the health and well-being of our employees and their families by providing comprehensive medical, dental, and vision coverage. Your health matters to us, and we invest in ensuring you have access to quality healthcare.
• Mental Well-Being: We understand the importance of mental health in fostering productivity and maintaining work-life balance. To support this, we offer initiatives such as No-Meeting Fridays, monthly company holidays, access to mental health resources, and a generous flexible time-off policy. Additionally, we embrace a remote-first culture that supports collaboration and flexibility, allowing our team members to thrive from any location. 
• Professional Development: Developing internal talent is a priority for Clover. We offer learning programs, mentorship, professional development funding, and regular performance feedback and reviews.

Additional Perks:

• Employee Stock Purchase Plan (ESPP) offering discounted equity opportunities
• Reimbursement for office setup expenses
• Monthly cell phone & internet stipend
• Remote-first culture, enabling collaboration with global teams
• Paid parental leave for all new parents
• And much more!

About Clover: We are reinventing health insurance by combining the power of data with human empathy to keep our members healthier. We believe the healthcare system is broken, so we've created custom software and analytics to empower our clinical staff to intervene and provide personalized care to the people who need it most.

We always put our members first, and our success as a team is measured by the quality of life of the people we serve. Those who work at Clover are passionate and mission-driven individuals with diverse areas of expertise, working together to solve the most complicated problem in the world: healthcare.

From Clover’s inception, Diversity & Inclusion have always been key to our success. We are an Equal Opportunity Employer and our employees are people with different strengths, experiences, perspectives, opinions, and backgrounds, who share a passion for improving people's lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All of our employee’s points of view are key to our success, and inclusion is everyone's responsibility.

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Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.