Staff Engineer

About Clever Benefits

Clever Benefits is building the tech that makes healthcare feel less like a headache. We package telemedicine services into custom-branded mobile apps and build the CRMs that power day-to-day operations for our clients. Our tools support meaningful experiences for the people who rely on them, and we're scaling quickly to meet demand.

We operate in a fast-paced, high-context environment with a lean engineering team that moves quickly and takes full ownership of its work. We care deeply about clarity, real-world impact, and building systems that scale. You won't find layers of red tape here—just a team of smart, mission-driven people solving hard problems together.

The Role

We're hiring a Staff Engineer to own the technical foundation and direction for our sister company, a third-party administrator delivering healthcare services in Oklahoma. This is a true full stack role with a strong backend focus and heavy infrastructure work in a regulated healthcare environment.

You'll be the owner and expert on the entire technical footprint for this organization. You'll shape the architecture, set technical standards, and drive the roadmap while remaining deeply hands-on with code. You'll own features end-to-end, from initial scoping and design through delivery, and make architectural decisions that position the platform for long-term success in a highly regulated space.

Key Responsibilities

• Own and drive the technical architecture and infrastructure for the organization
• Set engineering standards for code quality, testing, reliability, and security in a regulated environment
• Design, build, and deliver scalable, maintainable features across web, internal tooling, and infrastructure
• Lead system design discussions and make architectural decisions that balance regulatory requirements with product velocity
• Create sweeping improvements in stability, performance, and scalability across business-critical systems
• Identify and reduce complexity in projects, services, and processes to increase team effectiveness
• Set short to medium-term strategic technical direction, looking ahead 6-12 months to identify areas of greatest need

Who You Are

• 6+ years as a full stack engineer with a strong backend focus, building and scaling production systems in cloud environments
• Deep experience with our core stack: TypeScript, Node.js, React (with Vite and/or Next.js), tRPC, Prisma, and Tailwind CSS
• Strong experience with AWS infrastructure, particularly CDK, Fargate, RDS (PostgreSQL), and database integrations including Microsoft SQL Server
• Solid experience with CI/CD pipelines and GitHub Actions
• Track record of making significant positive impact on technical trajectory through architectural decisions and system improvements
• Passionate about system design, code quality, type-safety, and building for long-term maintainability
• Strong technical leader who can set direction, establish consensus, and remain hands-on with code
• Clear communicator who values collaboration and contributes to a positive, inclusive team culture
• Proactive, solution-oriented, and comfortable navigating ambiguity in a regulated environment
• Able to work on-site in Oklahoma City approximately 20-30% of the time on a regular cadence

Bonus points for:

• Experience working in regulated domains such as healthcare or handling HIPAA, SOC 1, or SOC 2 compliant systems
• Experience mentoring engineers and raising the technical bar across teams
• Background with database migrations or multi-database architectures
• History of simplifying complex systems and reducing technical debt
• Health insurance through Redirect Health 100% Employer-sponsored
• New Apple laptop provided
• 3 weeks PTO plus 9 Federal holidays