We’re a health insurance company that acts like a technology company. We’re using software, data science and telemedicine to make health insurance more affordable, easier to access and more of a delightful experience
Description
- We’re looking for a hands-on Service Operations Director to lead our DevOps and IT Operations functions. You will be responsible for the reliability, scalability, and cost-effectiveness of our infrastructure — across both development and production environments. Working closely with our Product and Engineering teams, you’ll drive strategic platform initiatives, ensure smooth internal tooling, and foster a strong culture of operational excellence.
- This is a leadership role that also requires rolling up your sleeves. You’ll mentor a small, bright, but relatively inexperienced team of 5, and lead by example as you scale our platform to new markets.
DevOps
- Own and manage the full lifecycle of infrastructure and operations — from development environments to live production systems
- Lead the ongoing migration from Kubernetes to Nomad, ensuring minimal disruption and clear documentation
- Oversee the CI/CD process using Octopus Deploy, driving improvements in deployment frequency and reliability
- Monitor system performance using New Relic and other observability tools; proactively resolve bottlenecks and incidents
- Collaborate with Product and Engineering on platform upgrades, internal tooling, and systems scalability
- Set up and maintain VOIP infrastructure (FreePBX) as we expand into new regions
- Define and refine incident response processes (business hours only), ensuring fast and transparent resolution
- Take ownership of infrastructure security practices, coordinating with the broader security approach of the company
- Educate and mentor your team, fostering growth in DevOps principles and operational excellence
- Track and manage cloud infrastructure costs, making data-informed decisions to optimize spend
- Define and monitor key KPIs: system availability, incident frequency/severity, and cost performance
IT Management
- Manage IT operations, including support for internal tools and systems
- Good Office365 knowledge and use of MS-Entra is essential
- Own (via local staff) relationships with suppliers of hardware
- Own and manage the connectivity of multiple office locations in 6 African countries
Requirements
- Proven experience leading DevOps or Service Operations in a scaling technology company
- Strong hands-on skills in cloud infrastructure (AWS), CI/CD, infrastructure-as-code, and monitoring (preferably with New Relic)
- Experience with Nomad, Octopus Deploy, Office365, and FreePBX is a strong plus
- A pragmatic problem-solver who can lead strategically while diving into technical details
- Excellent communicator who can explain infrastructure to technical and non-technical audiences
- Experience managing small teams and mentoring junior engineers
- Familiar with incident management processes and driving continuous improvement
- Comfortable working remotely, with 4–6 hours of overlap with UTC+1
Method of Application
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