DevOps Engineer, Sr. - 100% Remote

About the Company

Chexology is a technology company headquartered in New York City that develops software for hospitality and event operations. Its patented technology replaces traditional paper claim tickets for services such as coat check, luggage check, equipment rentals, and valet services. The company serves organizations including the Museum of Modern Art, Barclays Center, Live Nation, Tao Group, and Montage International.

About the Role

Chexology is seeking a Senior DevOps Engineer to take ownership of its infrastructure, deployment processes, database operations, and production reliability. Reporting to the Head of Engineering, you will help establish scalable infrastructure practices as the company grows, ensuring that applications remain reliable, secure, and easy to deploy.

This is a hands-on role within a small engineering team. You will manage AWS and Heroku infrastructure, improve CI/CD pipelines, strengthen observability and security, and optimize background processing and database operations. You will also work with application code, help resolve customer issues, and improve incident response practices. The focus is on building practical solutions that reduce operational overhead and allow engineers to concentrate on product development.

Key Responsibilities

• Manage and improve AWS and Heroku infrastructure using reproducible, automated practices.
• Introduce and maintain infrastructure as code to reduce manual configuration and undocumented processes.
• Build and refine observability through actionable dashboards, reliable alerting, and distributed tracing.
• Improve background-job processing, including queue visibility, job retries, stuck-job management, and queue architecture.
• Strengthen infrastructure security through secrets management, access controls, audit logging, and vulnerability management.
• Support enterprise security questionnaires and establish the technical foundations for SOC 2 compliance.
• Respond to infrastructure and security questions from current and prospective clients.
• Own Aurora MySQL database operations, including upgrades, performance tuning, backups, read replicas, and secure data access.
• Maintain read-only and personally identifiable information (PII)-free database schemas for internal tools and AI workflows.
• Improve CircleCI pipelines, build performance, review applications, and staging environments.
• Maintain safe, reliable, and reversible deployment processes.
• Establish practical runbooks, on-call procedures, incident response practices, and post-incident reviews.
• Monitor and optimize infrastructure costs while maintaining reliability.
• Contribute to Ruby on Rails application code, troubleshoot customer issues, and participate in support and off-hours maintenance rotations.
• Collaborate with engineers to improve platform reliability, operational efficiency, and developer productivity.

Required Qualifications

• At least 5 years of experience in DevOps, SRE, platform engineering, or infrastructure roles.
• Experience owning production systems that support live customers.
• Strong hands-on experience with AWS services, including database and storage infrastructure.
• Experience with platform-as-a-service deployment models, particularly Heroku.
• Strong knowledge of CI/CD pipelines, preferably CircleCI.
• Experience building and maintaining monitoring, alerting, and tracing systems.
• Database operations experience, including upgrades, performance tuning, backups, and replication; MySQL or Aurora experience is preferred.
• Practical knowledge of secrets management, access control, vulnerability management, and infrastructure security.
• Ability to work with application code and background-job systems, with willingness to learn Ruby on Rails where needed.
• Excellent written communication skills and the ability to work independently in a small team.
• A proactive approach to identifying problems, automating repetitive work, and improving operational processes.

Preferred Qualifications

• Experience with infrastructure-as-code tools such as Terraform or similar technologies.
• Experience migrating workloads from a PaaS to containerized or managed infrastructure without downtime.
• Experience supporting B2B SaaS platforms with multiple third-party integrations, including hospitality systems, messaging, and payment services.
• Background in hospitality technology, point-of-sale systems, or mobile and kiosk device fleets.
• Exper…