Senior DevOps Engineer

About Plenful

Plenful is on a mission to move pharmacy forward through intelligent automation. We build AI-powered software that eliminates administrative burden, strengthens compliance, and unlocks revenue across critical pharmacy workflows, solving one of the biggest challenges in healthcare today: delayed patient care.
Built by a passionate team of former healthcare operators and world-class AI technologists, Plenful combines deep domain expertise with enterprise-grade technology to automate complex workflows across intake authorization, 340B program optimization, and pharmacy revenue reconciliation. Our AI platform is trusted by 95+ leading healthcare organizations to power smarter, faster, and more resilient pharmacy operations.
Backed by leading investors including Notable Capital, Bessemer Venture Partners, and TQ Ventures, Plenful is building the institutional memory for healthcare and powering the most complex, highest ROI healthcare workflows. We’re actively hiring as we continue to scale.

Join our growing team!
About the role
We’re hiring a Senior DevOps Engineer to join our engineering team at Plenful and help build and scale the infrastructure, tooling, and deployment systems that power our product and engineering velocity. You’ll work across our distributed workflow engine, serverless pipelines, containerized services, and Postgres-based data layer. 

This role reports into engineering leadership and will play a key role in shaping how we build, deploy, and operate our platform as we continue to grow. You’ll focus on creating systems and workflows that enable engineers to move quickly and safely, while ensuring our platform remains reliable, observable, and efficient. 

You’ll bring strong technical judgment, a pragmatic approach to automation, and a focus on reducing friction for other engineers. You’ll collaborate closely with backend and ML teams and help shape a culture where infrastructure, reliability, and developer experience are clear, repeatable, and shared across the team.

What you’ll do
Infrastructure, Platform, and Deployment 

• Design, build, and evolve our cloud infrastructure using infrastructure-as-code, with a focus on scalability, consistency, and ease of use. 
• Build and maintain CI/CD pipelines that enable fast, safe, and repeatable deployments across our services. 
• Standardize deployment patterns across serverless workloads, containerized services, and workflow orchestration systems. 
• Improve how services are provisioned, configured, and deployed so engineers can move quickly without introducing risk. 

Developer Experience and Enablement 

• Develop internal tooling and automation to simplify common workflows across backend and ML teams. 
• Improve local and staging environments to reduce friction in development and testing. 
• Enable engineers to self-serve infrastructure through well-designed abstractions, templates, and documentation. 
• Identify and eliminate bottlenecks in the development and deployment lifecycle.

Observability, Reliability, and Performance 

• Define and evolve observability standards across metrics, logs, and tracing with a focus on actionable insights and system behavior. 
• Build systems that proactively detect reliability risks, latency regressions, and performance issues. 
• Partner with engineering teams to investigate and resolve performance bottlenecks across distributed systems, including serverless execution, containers, and Postgres. 
• Support incident response and contribute to root cause analysis, with a focus on preventing recurrence through better systems and automation. 

Security, Compliance, and Operational Excellence 

• Automate security and compliance workflows, including patching, access controls, audit readiness, and vulnerability management. 
• Embed security and compliance best practices into infrastructure and deployment pipelines. 
• Participate in the on-call rotation and respond to production issues with a focus on restoring service and improving systems over time. 
• Contribute to blameless postmortems and ensure learnings are reflected in tooling, processes, and documentation. 

What we’re looking for

• Bachelors Degree in Computer Science or related field
• 5+ years of professional engineering experience in a B2B, SaaS company. 
• Strong experience building and operating production systems in cloud environments, ideally AWS. 
• Hands-on experience with infrastructure as code (for example, Terraform), CI/CD systems, and modern deployment workflows. 
• Experience working with serverless compute patterns, containerized services, distributed workflows, and Postgres. 
• Solid understanding of observability tooling, performance debugging,, and system behavior under load. 
• Ability to write scripts or services to automate infrastructure and developer workflows. 
• A high ownership mindset, empathy for teammates, straightforward communication, and a one-team attitude. 
• Comfortable working in a fast-paced startup environment with a bias for action and thoughtful engineering judgment.

• Comprehensive Benefits Package: Enjoy unlimited PTO, fully covered health insurance (medical, dental, and vision), meal stipend, health & wellness stipend, 401(k) matching, and stock options.
• Mission-Driven, World-Class Team: Join an exceptional group of professionals aligned around a meaningful mission and committed to making an impact.
• Opportunities for Growth: Strengthen your partnership expertise through collaboration with experienced, high-performing leaders across the organization.
• Flexible Work Environment: Employees based in the Bay Area enjoy two days per week in a brand-new downtown San Francisco office. Employees based in other cities enjoy a fully remote work environment with the ability to travel for collaboration.