Senior DevOps Engineer, (Senior Consultant, Engineering & Technical Services)

About the Role

At Fearless, the DevOps Engineer works at an advanced level of proficiency alongside cross-functional Agile teams to build, secure, and operate the cloud infrastructure and delivery pipelines behind a federal health care platform serving approximately 11 million monthly users. Blending deep DevOps automation with security and federal compliance (FedRAMP, FISMA, NIST 800-53) across the software and data lifecycle, this role manages cloud and edge infrastructure, CI/CD, and observability — while serving as a technical go-to who mentors engineers, champions secure engineering best practices, and advises the client and Fearless leadership. The successful candidate pairs advanced infrastructure-automation expertise with strong security engineering to deliver secure, efficient, and scalable solutions that directly impact mission delivery.

Eligibility Requirements

• Completion of DevSecOps take-home exercise.
• CMS residency requirement documentation (U.S. residency for at least 3 of the last 5 years).
• Ability to pass a Federal background check.
• Ability to obtain and maintain a federal Public Trust clearance.

Place of Performance & Travel Requirements

While this role is primarily remote, candidates must meet CMS residency requirements.

Responsibilities

• Design, automate, and secure cloud and edge infrastructure across major cloud platforms (AWS, Azure, or GCP) and CDN/edge services (Akamai, Cloudflare, or CloudFront), including Web Application Firewall (WAF) configuration for security and performance.
• Manage infrastructure as code using tools such as Terraform or CloudFormation.
• Build and maintain CI/CD pipelines (GitHub Actions, GitLab CI, or Jenkins) and script automation in Python, Bash, or Go, with security integrated into the pipeline.
• Containerize and operate applications with Docker/Kubernetes and support local development environments (e.g., DDEV).
• Stand up and maintain monitoring, logging, and alerting systems (e.g., Splunk, Prometheus, Grafana, Datadog).
• Embed federal security and compliance (FedRAMP, FISMA, NIST 800-53) across delivery and generate audit evidence.
• Collaborate directly with the external client and partner contractors, and across development teams and stacks, within a two-week Agile delivery model.
• Identify and remediate infrastructure and application security risks; champion secure engineering best practices.
• Serve as a technical go-to ("the person to ask") for cloud infrastructure, CI/CD, and security questions; mentor and coach engineers to elevate team capability and technical expertise.
• Align the technical approach with product and project goals, anticipate risks early, and advise the client and Fearless leadership as a trusted advisor.

Impact You Will Create

• Fosters collaboration with cross functional teams by taking the initiative and driving conversations
• Coach, mentor, and develop peers that elevate team capability and technical expertise using clear and persuasive communication of engineering solutions to both technical and non-technical audiences
• Earn the trust of your customer and teammates by delivering world class services.
• Drive accountability and delivery by ensuring project objectives are not only met on time but aligned with client priorities and Fearless standards of excellence.
• Anticipate risks and implement proactive solutions to keep initiatives on track.
• Take ownership of risk management by monitoring deliverables across the team, identifying issues early, and coaching teammates on mitigation strategies while keeping leadership informed.
• Shape client engagement and intelligence-gathering efforts by actively cultivating relationships with stakeholders, synthesizing insights across the client organization and partner ecosystem, and providing Fearless leaders with actionable recommendations that inform strategy and strengthen delivery outcomes.

Customer Impact

• Deliver expected outcomes relative to high quality code and maintainable systems
• Offer and implement innovative solutions that include engineering best practices through new tools, frameworks and methodologies
• Lead and align stakeholders with product and project goals that advance customer satisfaction as well as Fearless’ objectives, strategy, and mission
• Serve as a trusted advisor in your area of expertise

Work Experience

• 7+ years of engineering experience with a track record of working in Agile, cross-functional teams.
• Experience working directly with external clients and partner contractors.
• Familiarity with Service Delivery Frameworks for government.
• Experience managing federal compliance frameworks (FedRAMP, FISMA, NIST 800-53) and generating audit evidence.
• Cloud & Edge Infrastructure: hands-on experience with major cloud platforms (AWS, Azure, or GCP) and edge/CDN services (Akamai, Cloudflare, or CloudFront) to manage web application security (WAF) and performance.
• Infrastructure as Code (IaC): deep understanding of managing infrastructure using tools like Terraform or CloudFormation.
• CI/CD & Automation: proficiency in building and maintaining continuous integration and deployment pipelines (GitHub Actions, GitLab CI, or Jenkins) and scripting automated tasks in Python, Bash, or Go.
• Containerization & Local Dev: experience containerizing applications with Docker/Kubernetes (experience with local environments like DDEV is a strong plus).
• Application & Architecture Familiarity: comfort collaborating with developers across various stacks.
• Observability: experience setting up monitoring, logging, and alerting systems (e.g., Splunk, Prometheus, Grafana, Datadog).

Nice to Have

• Specific experience with Drupal 11 architecture and APIs, or modern JS frameworks (Node.js, Next.js, React).
• Relevant certifications (e.g., AWS Certified DevOps Engineer, CKA, HashiCorp Terraform Associate).
• Experience scaling relational and non-relational databases (MySQL, PostgreSQL, Redis).
• Experience with serverless architectures (AWS Lambda) and AI-assisted development tools (e.g., GitHub Copilot) for secure code generation.

Skills and Competencies

• Analytical Thinking: The ability to observe and interpret information, break down complex problems into parts, identify patterns/relationships and draw logical conclusions to develop effective solutions.
• Synthetic Thinking: The ability to combine different ideas, information, or concepts to create a new, complex understanding or solution by integrating disparate elements into a new, meaningful whole.
• Adaptability: Comfort with change, flexibility in the face of shifting demands and resilience to setbacks.
• Ownership & Accountability: Committed to taking responsibility for outcomes, ensuring that all commitments are met with a focus on enhancing service delivery.
• Consultative Advising: Identifies and articulates client challenges, scopes projects and aligns recommendations to business goals and client expectations.
• Communicating with Influence: Capable of crafting and delivering clear, persuasive messages that integrate data insights and structured narratives, tailored to the strategic needs of diverse audiences to drive effective decision-making.
• Managing Priorities & Client Alignment: Skillfully negotiates and manages conflicting priorities to strategically align decisions, enhancing service delivery and client satisfaction.

Required Level of Proficiency

You can perform the actions associated with a skill without assistance. You are recognized within your immediate organization as "a person to ask" when difficult questions regarding required skills arise.

Physical Requirements

• Ability to sit for extended periods while working on a computer or during meetings.
• Must be able to travel occasionally to client sites or company meetings, which may involve driving or flying.
• Ability to communicate effectively via phone, email, and in-person, requiring clear speech, listening, and written communication skills.
• Ability to move within an office environment, including reaching for files, using office equipment, and occasional light lifting (up to 10 pounds).

Benefits

For Full-Time Team Members (Starting Day One):

• Flexible, life-friendly schedules
• 100% coverage for our medical HSA plan + HSA contributions
• Dental & vision covered 100% for you and your dependents
• Competitive premiums for HMO/PPO and dependent coverage
• 401(k) with 4% match & immediate vesting
• Paid Parental Leave and 12 weeks paid FMLA
• Generous PTO, 11 Federal Holidays, a Birthday Holiday, and Sick Leave
• Up to 15 days for Jury Duty and Bereavement Leave
• Education, wellness, and tech allowances
• Referral bonus: $6K–$12K for each successful referral
• Pet insurance & discount plans
• Employee Assistance Program (EAP)
• Legal support, life insurance, disability coverage
• Performance-Based Bonuses: We believe your impact should be recognized. Our bonus program rewards both shared company success and individual contributions.

Compensation

Fearless is committed to providing a competitive compensation package that will meet your current and future needs. Our philosophy is aimed at rewarding team member contributions, supporting long-term financial growth and security, and overall well-being. We believe in paying people fairly, so we've established a compensation model aimed to ensure everyone at Fearless — regardless of race, ethnicity, gender, sexual orientation, disability, religion, age, nationality, or willingness/ability to negotiate — is consistently paid fairly based on alignment to the needs and requirements of the role.

Salary Range for this Position:
Minimum Salary: $120,588
Salary Midpoint: $156,764
Maximum Salary: $195,955
Hiring Range for Role: $120,588 - $160,000

This position is eligible for a discretionary bonus based on individual and company performance criteria.