Senior DevOps Engineer

Medasync is looking for a hands-on Senior DevOps Engineer to help make our AWS environment more consistent, secure, reliable, and straightforward for engineers to work with.

This is a senior individual-contributor role with meaningful architectural influence. You will work closely with the CTO, lead engineer, and application developers to shape infrastructure patterns, improve delivery practices, and turn sound application designs into maintainable production systems. We value people who bring informed opinions and establish standards through collaboration and implementation, not by fiat.

Our developers remain accountable for the services they build. This role is not intended to become a deployment gatekeeper or a place where teams throw work over the fence. Instead, you will help developers make informed infrastructure decisions, provide reusable patterns and tooling, and take primary responsibility for implementing and maintaining the infrastructure-as-code that supports those systems.

Our software supports Skilled Nursing Facilities that operate around the clock and use patient data to improve billing accuracy, care-quality analysis, and audit defensibility. The stability and security of our systems matter because our customers depend on them while serving vulnerable patient populations.

What You’ll Do

• Own and evolve our AWS infrastructure, with ECS/Fargate and Lambda as the primary application runtimes.

• Support the broader AWS environment, including RDS PostgreSQL, EC2-hosted SQL Server instances, bastion hosts, DMS, Glue, Athena, and other supporting services.

• Inventory legacy, manually configured, and serverless-managed infrastructure and bring it under Terraform and Terragrunt.

• Build and maintain reusable Terraform modules, environment patterns, and deployment conventions that reduce drift and make infrastructure changes easier to review.

• Lead the migration from Bitbucket and CircleCI to GitHub and GitHub Actions.

• Improve CI/CD reliability, deployment traceability, secrets handling, environment promotion, rollback practices, and developer feedback.

• Own the technical implementation and remediation of SOC 2 controls across existing and new infrastructure.

• Strengthen controls related to access management, least privilege, logging, monitoring, encryption, change management, vulnerability remediation, backups, recovery, and infrastructure evidence collection.

• Work with the CTO, lead engineer, and developers during application and systems design to identify operational, security, and reliability concerns before deployment.

• Establish practical infrastructure and delivery standards while allowing teams room to make context-appropriate engineering decisions.

• Create documentation, templates, and paved paths that help developers ship safely without turning DevOps into a centralized ticket queue.

• Improve observability, alerting, runbooks, backup validation, recovery procedures, and general operational readiness.

• Participate in shared engineering on-call and incident response, taking the lead when an incident primarily involves AWS, infrastructure, networking, deployment systems, or data-platform operations.

• Help investigate infrastructure and database performance issues by understanding how compute, storage, networking, connection management, and workload design affect system behavior.

• Identify opportunities to improve the security, reliability, maintainability, and cost-effectiveness of the AWS environment.

Initial Priorities

During the first 6-12 months, your work will center on three major outcomes:

• Infrastructure normalization: Bring legacy, manually managed, and partially automated AWS resources into a consistent Terraform/Terragrunt model.
• Source-control and delivery migration: Move repositories and CI/CD workflows from Bitbucket and CircleCI to GitHub and GitHub Actions while improving the existing delivery process.
• SOC 2 technical readiness: Identify and remediate technical control gaps, improve the consistency of controls across environments, and make evidence collection more systematic and repeatable., Architecture is shaped collaboratively by the CTO, lead engineer, developers, and the people closest to the problem. We expect this person to bring ideas, challenge assumptions constructively, and help us improve our standards.

Application developers remain responsible for understanding how their services run and for participating in operational support. The Senior DevOps Engineer provides deeper infrastructure expertise, develops the implementation patterns, and removes the specialized infrastructure work that currently creates a bottleneck for product development.

The role is also not intended to be a dedicated DBA or data-engineering position. You will own the infrastructure, security, backup, monitoring, and operational health surrounding our data systems, while application and data owners remain responsible for schemas, data models, and application-level query behavior.

We care more about demonstrated scope, judgment, and ownership than a particular number of years in the field.

You should bring:

• Senior-level experience owning or substantially improving production AWS environments.

• Strong hands-on experience with Terraform, including reusable modules, remote state, multiple environments, dependency management, drift, imports, and the migration of existing resources into infrastructure-as-code.

• Experience designing, operating, or substantially improving CI/CD systems.

• Experience supporting containerized and serverless workloads in AWS.

• A strong working knowledge of cloud security fundamentals, including IAM, least privilege, network boundaries, secrets management, encryption, logging, and auditability.

• A security-oriented mindset and the ability to evaluate infrastructure decisions in the context of a regulated environment.

• Sound judgment about reliability, maintainability, security, delivery speed, and operational complexity.

• Experience collaborating with application engineers on deployment architecture rather than treating infrastructure as a downstream implementation task.

• The ability to translate recurring infrastructure needs into reusable patterns, documentation, and automation.

• Practical knowledge of Linux, containers, networking, DNS, TLS, monitoring, alerting, backups, and incident response.

• Broad awareness of the infrastructure factors that affect relational databases and data-processing systems. Deep DBA, data-engineering, or data-modeling expertise is not required.

• The ability to read and reason about application architecture and code well enough to support Python services built with frameworks such as FastAPI and Django.

• Clear written and verbal communication, including the ability to explain tradeoffs, document decisions, and influence technical direction without relying on positional authority.

Direct experience with AWS and Terraform is important. We do not expect candidates to have used every other tool in our current stack, provided they have strong experience with comparable technologies and can learn new systems quickly.

Helpful, but Not Required

• Terragrunt experience.

• Experience migrating from Bitbucket to GitHub or from CircleCI to GitHub Actions.

• Hands-on experience with ECS, Fargate, Lambda, RDS, EC2, DMS, Glue, or Athena.

• Experience implementing or remediating SOC 2 technical controls.

• Experience automating compliance evidence or working alongside security and audit teams.

• Experience in healthcare, financial services, or another regulated industry.

• Familiarity with HIPAA security requirements.

• Operational experience with PostgreSQL or SQL Server.

• Experience gradually replacing manually managed or inconsistent infrastructure without disrupting active production systems.

• Interest in growing from technical compliance ownership into broader security or compliance-program leadership.

Pulled from the full job description Health insurance Vision insurance Health savings account Dental insurance, * Dental insurance

• Health insurance
• Health savings account
• Vision insurance