Senior DevOps Lead / Infrastructure Engineer

Job Title: Senior DevOps Lead / Infrastructure Engineer

Salary: Competitive

Location: Remote (USA or Canada)

As the Senior DevOps Lead, you will be a key leader in our engineering organization, reporting directly to the Director of Platform. You will be responsible for managing our AWS infrastructure, automating deployment processes, and ensuring strict compliance with industry standards such as SOC2 and HIPAA. As we prepare for massive enterprise scaling—including a 1-million-user state-wide rollout and integrations with Fortune 500-level clients—this role involves maintaining high availability, scalability, and security of our cloud environment. You will work closely with our global engineering teams (operating primarily on EST) and our leadership team (PST) to streamline our development and release cycles. This is a high-ownership role with a direct impact on engineering velocity and enterprise trust.

Our Technical Environment: You’ll operate across a modern, evolving stack that includes:

• AWS (EC2, ECS, RDS, S3, CloudFront, Lambda, IAM, VPC) and Terraform
• GitHub Actions as our primary CI/CD platform
• Docker-based containerized services
• Kubernetes for scalable and reliable container orchestration.
• Familiarity with Jenkins is needed to support and maintain legacy build and deployment pipelines.
• MongoDB and MySQL data stores
• ETL and enterprise reporting pipelines
• React and React Native applications
• Node.js backend services
• Enterprise integrations (SSO, SCIM, payroll systems, rewards providers)
• Experience with Azure AD and Okta is required for identity and access management solutions.
• AWS Transfer Family to enable secure and managed file transfer services.
• SOC2 Type 2 and HIPAA-aligned environments
• Microsoft Intune (MDM/MAM) for automated device provisioning and policy enforcement.
• Zscaler (ZIA/ZPA) for secure access service edge (SASE) and private application connectivity.
• Centralized security dashboards and SIEM integrations for real-time threat monitoring

We are actively modernizing toward:

• Infrastructure as Code across all environments
• Fully automated deployments with rollback strategies
• Improved microservice boundaries
• Strong observability with SLO-driven monitoring
• AI-assisted DevOps automation

We believe in AI-first DevOps, not manual. We are not looking for someone to maintain pipelines. We are looking for someone to evolve them.

Why Join Us?

• Impact: Take ownership of our core infrastructure and deployment pipeline, directly influencing product reliability and speed to market for major enterprise contracts.
• Growth: This senior-level position offers significant opportunities to architect and implement modern DevOps practices, expand your leadership skills, and work directly with our North American leadership team.
• Autonomy: Lead the vision for our infrastructure and deployment strategy, with the freedom to implement best practices.
• Scale: Work on a multi-tenant B2B platform serving massive enterprise customers with rigorous compliance and traffic requirements.
• Modernization: Help transition from evolving monolith services to containerized and scalable architecture patterns.
• Automated Governance: Real-time compliance dashboards and self-healing security configurations

What You’ll Do:

• Infrastructure Management: Design, implement, and manage the company's AWS cloud infrastructure, ensuring performance, security, and cost efficiency at a 1M+ user scale.
• Deployment Automation: Automate our continuous integration and continuous deployment (CI/CD) pipelines to enable fast, reliable, and frequent software releases across distributed time zones.
• Compliance & Security: Implement and maintain configurations and processes to meet industry compliance standards, including SOC2, HIPAA, and other relevant security frameworks required by our enterprise partners.
• Monitoring & Reliability: Develop comprehensive monitoring and logging strategies to proactively identify and resolve system issues, ensuring high system uptime and reliability.
• Collaboration: Work closely with software development, AI, and QA teams to integrate automated testing and security into the deployment lifecycle.
• Disaster Recovery & Business Continuity: Establish and regularly test disaster recovery and business continuity plans for critical systems.
• Zero Trust & Secure Access: Orchestrate and manage Zscaler (ZIA/ZPA) to ensure secure, private connectivity for a distributed workforce and enterprise integrations.
• Unified Endpoint Management: Own the Microsoft Intune environment to automate device provisioning, security patching, and policy enforcement across the organization.
• Security Observability: Architect real-time security dashboards to monitor our compliance posture, ensuring we remain audit-ready for SOC2, HIPAA, and partner-specific security requirements.

What You Bring:

• Experience: 5+ years in a DevOps, Site Reliability, or Infrastructure Engineering role, with significant experience managing AWS cloud services at an enterprise scale.
• Technical:
• Deep expertise in Infrastructure as Code (Terraform preferred).
• Experience with Docker and container orchestration (ECS or Kubernetes).
• CI/CD expertise (GitHub Actions, AWS CodePipeline preferred).
• Hands-on experience with AWS SQS and RabbitMQ is needed for building reliable and decoupled messaging workflows.
• Compliance: Proven track record of implementing and maintaining strict compliance requirements (e.g., SOC2, HIPAA) in a cloud environment.
• Skills: * Strong scripting and programming skills (e.g., Python, Bash).
• Excellent troubleshooting, incident response, and root cause analysis skills.
• Experience with capacity planning and performance optimization for high-traffic platforms.
• Experience implementing automated rollback strategies.
• Mindset: Proactive, self-directed leader with a passion for building scalable and resilient systems. Comfortable operating in a fast-paced startup environment and collaborating with distributed teams working across EST and PST.

What You’ll accomplish in your first 90 Days:

• Audit and improve current CI/CD workflows.
• Identify infrastructure scalability and security gaps ahead of major enterprise rollouts.
• Reduce manual deployment steps.
• Improve monitoring coverage and incident visibility.
• Propose a modernization roadmap for infrastructure and automation.

What We Offer

• Comprehensive Wellness Benefits: Company-paid medical, dental, and vision, plus unlimited personal coaching.
• Flexible Work: Remote-first environment with dedicated wellness and recharge days.
• Financial Support: 401(k) program and financial coaching.
• Time to Recharge: PTO, paid company holidays, plus floating holidays of your choice.

Wellness Coach is dedicated to diversity and inclusion and is proud to be an equal opportunity employer. We welcome all qualified applicants without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.