Senior DevOps Engineer

About Waymark

Waymark is a mission-driven team of healthcare providers, technologists, and builders working to transform care for people with Medicaid benefits. We partner with communities to deliver technology-enabled, human-centered support that helps patients stay healthy and thrive. We’re designing tools and systems that bring care directly to those who need it most—removing barriers and reimagining what’s possible in Medicaid healthcare delivery.Our ValuesAt Waymark, our values are the foundation of how we work, grow, and support one another:

• Bold Builders: We tackle the toughest challenges in care delivery by harnessing the power of community and technology.
• Humble Learners: We seek feedback, embrace diverse perspectives, and welcome challenges to our assumptions.
• Experiment to Improve: We use data to inform decisions and continuously assess our performance.
• Focused Urgency: Our mission drives us to act swiftly and relentlessly in pursuit of meaningful results.

If this resonates with you, we invite you to bring your creativity, energy, and curiosity to Waymark.

About this role

At Waymark, our infrastructure directly enables care delivery — the tools built and operated here are used every day by community health workers, social workers, pharmacists, and care coordinators supporting patients with Medicaid benefits.As a Senior DevOps Engineer, you'll own projects from design through delivery, working closely with software and data engineers to keep our systems (dBt, Redshift) reliable and our teams moving. You communicate proactively, mentor junior engineers, and bring new ideas to the team — not just implementing what's asked, but helping shape how we build and operate.This is a role for someone who wants to do meaningful work at the intersection of technology and healthcare equity.Key Responsibilities

• Build, deploy, and maintain scalable, highly available systems on AWS
• Own CI/CD pipelines and drive improvements to deployment automation
• Own and evolve infrastructure as code using Terraform and Ansible
• Research new tools and technologies, develop proofs of concept, and introduce validated practices to the team
• Improve system reliability — sharpen alerting, build out runbooks, and deepen observability across our stack (Grafana, Loki, Mimir, Tempo)
• Participate in an on-call rotation; off-hours incidents are rare thanks to extensive automation and self-healing — occasional evening work is limited to planned maintenance and system upgrades
• Maintain process documentation, operational runbooks, and infrastructure diagrams
• Help maintain and manage systems for other teams
• dBt and Redshift – to support our Analytics Team
• SageMaker – to support our Data Science Team
• Raise the DevOps literacy of the engineering team — mentoring junior engineers and helping non-infrastructure engineers build good practices around deployments, observability, and reliability
• Collaborate with engineering teams on infrastructure design decisions

Minimum Qualifications

• 5+ years of experience designing, implementing, and operating highly available, fault-tolerant systems in cloud environments
• Hands-on experience with AWS (EC2, ECR, CloudFront, Route 53, etc)
• Experience with containerization and workload orchestration (Docker, Nomad)
• Proficiency with infrastructure as code tools (Terraform, Ansible)
• Strong knowledge of CI/CD practices including automated testing and deployment automation
• Strong Linux and shell/bash scripting skills
• Experience with relational databases (PostgreSQL) and messaging systems (RabbitMQ)
• Experience working in a regulated or compliance-driven environment (e.g. HIPAA, SOC 2, PCI, FedRAMP)

Preferred Qualifications

• Experience with service mesh and secrets management (Consul, Vault)
• Experience with data platforms and pipelines (dBt, SageMaker, Redshift)
• Experience with networking and DNS
• Experience with image building and provisioning automation (Packer)
• Programming experience (Python, Elixir, TypeScript)
• Exposure to Google Cloud (GCP)

Hiring Range

US Employees in San Francisco/Bay Area, New York City - $140,000 - $194,000

US Employees in Boston, Los Angeles, Seattle, Washington DC - $129,000 - $179,000

US Employees in Arlington, Denver, San Diego, Sacramento - $123,000 - $172,000

US Employees in Albany, Atlanta, Austin, Baltimore, Central/Southern, Charlotte, Chicago, Dallas/Fort Worth, Detroit, Houston, Las Vegas, Miami, Milwaukee, Philadelphia, Portland, Research Triangle, Salt Lake City, Twin Cities - $112,000 - $156,000

US Employees in Baton Rouge, Birmingham, Charleston, Cincinnati, Cleveland, Daytona Beach, Indianapolis, Nashville, New Orleans, Omaha, Phoenix, Pittsburgh, St. Louis, Tampa - $109,000 - $151,000

In addition to salary, we offer a comprehensive benefits package. Here’s what you can expect:

Stock Options: Opportunity to invest in the company’s growth.

Work-from-Home Stipend: A dedicated stipend for your first year to help set up your home office.

Medical, Vision, and Dental Coverage: Comprehensive plans to keep you and your family healthy.

Life Insurance: Basic life insurance to give you peace of mind.

Paid Time Off: 20 vacation days, accrued over the year, plus 11 paid holidays.

Parental Leave: 16 weeks of paid leave for birthing parents after six months of employment, and 8 weeks of bonding leave for non-birthing parents.

Retirement Savings: Access to a 401(k) plan with a company contribution, subject to a vesting schedule.

Commuter Benefits: Convenient options to support your commute needs.

Professional Development Stipend: A dedicated stipend supports professional development and growth.

Offer of employment is contingent upon successful completion of a background check. Employment history and advance degree verification (when applicable) are included as part of the standard background check process. 

Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that some of us may be less likely to apply to jobs unless we meet every single qualification. Waymark is dedicated to building a supportive, equal opportunity, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every preferred qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!