📍 Job Overview

Job Title: Senior DevOps Engineer – API & Business Services
Company: Progyny, Inc.
Location: New York, New York (Remote)
Job Type: Full-Time, Hybrid (3 days in office)
Category: DevOps Engineer
Date Posted: June 27, 2025
Experience Level: 7+ years in DevOps or platform engineering roles
Remote Status: Hybrid (Remote/On-site)

🚀 Role Summary

Key web technology aspect 1: Serve as a Senior DevOps Engineer supporting the API & Business Services team, enabling secure and scalable access to internal and external systems.
Key web technology aspect 2: Collaborate with a pod of engineers to support automated, repeatable build and deploy of solutions and services across the technology platform.
Key web technology aspect 3: Improve developer experience, automate quality assurance functions, and support effective solutions engineering at Progyny.
Key web technology aspect 4: Contribute to platform-wide standards and maintain awareness of industry patterns and practices evolution.

📝 Enhancement Note: This role requires a strong background in DevOps and platform engineering, with a focus on containerized environments, Infrastructure as Code, and GitOps automation. The ideal candidate will have experience working with AWS and various build management solutions.

💻 Primary Responsibilities

Web technology responsibility 1: Design and support the automated, repeatable build and deployment of Progyny's solutions to ensure an exceptional experience for members and lowest-friction developer experience.
Web technology responsibility 2: Collaborate with the API & Business Services team to ensure reliable and secure access to internal and external systems.
Web technology responsibility 3: Contribute to platform-wide standards and best practices, maintaining awareness of industry trends and emerging technologies.
Web technology responsibility 4: Troubleshoot and resolve technical issues, optimizing performance and ensuring system reliability.
Web technology responsibility 5: Participate in on-call rotations and provide support for production environments as needed.

📝 Enhancement Note: This role requires strong problem-solving skills and the ability to work effectively in a remote, collaborative environment. The ideal candidate will be comfortable working with multiple technologies and able to adapt to changing priorities.

🎓 Skills & Qualifications

Education: Bachelor's degree in Computer Science, Engineering, or a related field. Relevant work experience may be considered in lieu of a degree.

Experience: 7+ years in DevOps or platform engineering roles for a moderate-to-large-sized software engineering organization.

Required Skills:

Experience with containerized environments (Helm charts, Docker, Kubernetes, etc.)
Solid experience with Infrastructure as Code (IaC) models and Terraform/HCL conventions
5+ years of GitOps automation on common SCM platforms (GitHub, GitLab)
Deep experience with Git-flow and code branch management models
3+ years working with AWS (VPC, IAM, etc.)
Proven ability to anticipate CI/CD considerations for distinct platform components and environment constraints
Proven experience with various build and package management solutions and toolchains
Demonstratable knowledge of authentication and authorization access patterns
Experience deploying and maintaining observability tools (Grafana, Prometheus, Sentry, etc.)
Demonstratable networking knowledge (TCP stack, CIDRs, DNS, troubleshooting, etc.)
Familiarity with orchestrating modern data platforms (Dagster, Apache Airflow)
Experience supporting API gateway middleware (KrakenD, Kong, Tyk)
Experience evaluating or implementing internal developer tools (Airtable, Budibase, Metabase, n8n, OpenMetaData)
Demonstratable security knowledge (PKI, restricted data, etc.) and integration to relevant source systems
Demonstratable Linux and shell skills
Demonstratable SCM skills
Comfortability with Bash and Python

Preferred Skills:

Experience working in a regulated business environment (e.g., Healthcare)
Familiarity with modern data platforms and data pipelines
Experience with cloud security and compliance frameworks (e.g., CIS, NIST, ISO 27001)

📝 Enhancement Note: The ideal candidate will have a strong background in DevOps and platform engineering, with a focus on containerized environments, Infrastructure as Code, and GitOps automation. Experience working with AWS and various build management solutions is also highly desirable.

📊 Web Portfolio & Project Requirements

Portfolio Essentials:

Demonstrate experience with containerized environments, Infrastructure as Code, and GitOps automation through relevant projects and case studies.
Showcase your ability to design and implement reliable and secure APIs and data services.
Highlight your experience with AWS and various build management solutions.
Include examples of your problem-solving skills and ability to optimize performance and ensure system reliability.

Technical Documentation:

Include detailed documentation of your code, including comments, version control, and deployment processes.
Provide examples of your approach to testing methodologies, performance metrics, and optimization techniques.
Demonstrate your ability to collaborate effectively with other engineers and contribute to platform-wide standards and best practices.

📝 Enhancement Note: The ideal candidate will have a well-organized and comprehensive portfolio that showcases their technical skills and ability to work effectively in a remote, collaborative environment.

💵 Compensation & Benefits

Salary Range: The annual salary range for NYC-based applicants is $165,000 - $175,000 USD. Progyny offers a total compensation package comprised of base salary, cash bonus, and equity.

Benefits:

Family friendly benefits: Paid family and parental leave, preconception, fertility and family building benefits, family and pet care fund, and parents' employee affiliation group.
Menopause and midlife care
Health, dental, vision, and life insurance options for employees and family
Free in-person, virtual, and text-based mental health and wellness support
Paid time off, including vacation, sick leave, personal days, and summer flex time
Company equity and bonus program
401(k) plan with company match
Access to on-demand legal and financial advice
Learning and development programs and mentorship program
Company social events, including annual volunteer day and donation matching
Flex days (3 days a week in the office) and onsite meals and snacks for employees reporting into the NY office

📝 Enhancement Note: Progyny offers a competitive benefits package that prioritizes the well-being and work-life balance of its employees.

🎯 Team & Company Context

Company Culture:

Industry: Progyny is a global leader in women's health and family building solutions, trusted by leading employers, health plans, and benefit purchasers.
Company Size: Progyny has a lean remote team of experienced polyglot engineers, with a focus on effective collaboration and communication.
Founded: 2016, with headquarters in New York City.

Team Structure:

The DevOps guild members support the design and support of automated, repeatable build and deployment of Progyny's solutions.
The API & Business Services team serves as the centralized integration and data services layer for the company, enabling secure and scalable access to internal and external systems.
The DevOps guild contributes to platform-wide standards and best practices, maintaining awareness of industry trends and emerging technologies.

Development Methodology:

Progyny follows the goal of being cloud native with modern patterns and thoughtful selection of technology solutions.
The platform follows GitOps and automation principles, with a clear eye on security/privacy control considerations among multiple other sibling non-functional considerations.
The team emphasizes communication and collaboration through practice guilds, peer development, documenting decisions and plans, and maintaining awareness of industry patterns and practices evolution.

Company Website: www.progyny.com

📝 Enhancement Note: Progyny's culture emphasizes effective collaboration and communication, with a focus on supporting the family building journey of millions of individuals. The ideal candidate will be comfortable working in a remote, collaborative environment and able to adapt to changing priorities.

📈 Career & Growth Analysis

Web Technology Career Level: Senior DevOps Engineer, responsible for supporting the API & Business Services team and contributing to platform-wide standards and best practices.

Reporting Structure: The Senior DevOps Engineer will report directly to the Engineering Manager of the API & Business Services team and collaborate with other engineers and guild members.

Technical Impact: The Senior DevOps Engineer will have a significant impact on the reliability, performance, and security of Progyny's APIs and data services. They will work closely with the API & Business Services team to ensure secure and scalable access to internal and external systems.

Growth Opportunities:

Growth opportunity 1: Contribute to platform-wide standards and best practices, maintaining awareness of industry trends and emerging technologies.
Growth opportunity 2: Gain experience with modern data platforms and data pipelines, expanding your technical skill set and expertise.
Growth opportunity 3: Develop leadership skills and contribute to the technical direction of the DevOps guild and API & Business Services team.

📝 Enhancement Note: Progyny offers opportunities for growth and development, with a focus on expanding technical skills and expertise. The ideal candidate will be proactive in seeking out new challenges and learning opportunities.

🌐 Work Environment

Office Type: Hybrid, with 3 days in the office and remote work options available.

Office Location(s): Progyny's headquarters is located in New York City, with remote team members across the United States.

Workspace Context:

Workspace aspect 1: Progyny's hybrid work environment allows for effective collaboration and communication, with a focus on supporting the family building journey of millions of individuals.
Workspace aspect 2: Progyny provides the necessary tools and resources for remote work, including access to onsite meals and snacks for employees reporting into the NY office.
Workspace aspect 3: Progyny's culture emphasizes communication and collaboration through practice guilds, peer development, documenting decisions and plans, and maintaining awareness of industry patterns and practices evolution.

Work Schedule: Progyny offers flexible working hours, with a focus on supporting work-life balance and the well-being of its employees.

📝 Enhancement Note: Progyny's hybrid work environment allows for effective collaboration and communication, with a focus on supporting the family building journey of millions of individuals. The ideal candidate will be comfortable working in a remote, collaborative environment and able to adapt to changing priorities.

📄 Application & Technical Interview Process

Interview Process:

Process step 1: Technical preparation and coding/configuration assessment, focusing on containerized environments, Infrastructure as Code, and GitOps automation.
Process step 2: Web architecture expectations and system design discussion, with a focus on secure and scalable APIs and data services.
Process step 3: Collaboration and communication assessment, with a focus on effective collaboration and communication in a remote environment.
Process step 4: Final evaluation criteria and technical impact discussion, with a focus on the role's impact on Progyny's APIs and data services.

Portfolio Review Tips:

Portfolio tip 1: Tailor your portfolio to showcase your experience with containerized environments, Infrastructure as Code, and GitOps automation.
Portfolio tip 2: Include examples of your ability to design and implement reliable and secure APIs and data services.
Portfolio tip 3: Highlight your problem-solving skills and ability to optimize performance and ensure system reliability.
Portfolio tip 4: Demonstrate your ability to collaborate effectively with other engineers and contribute to platform-wide standards and best practices.

Technical Challenge Preparation:

Challenge preparation 1: Familiarize yourself with Progyny's technology stack, including containerized environments, Infrastructure as Code, and GitOps automation.
Challenge preparation 2: Prepare for architecture and design questions related to secure and scalable APIs and data services.
Challenge preparation 3: Practice your communication and collaboration skills, with a focus on effective communication in a remote environment.

ATS Keywords:

Programming Languages: Python, Bash, Infrastructure as Code (Terraform/HCL), Git, AWS (VPC, IAM), Containerization (Docker, Kubernetes), GitOps Automation, CI/CD, Build Management, Observability Tools, Networking, API Gateway Middleware, Security, Linux, Shell
Web Frameworks & Libraries: N/A (focus on backend and infrastructure technologies)
Server Technologies: AWS (VPC, IAM), Containerization (Docker, Kubernetes), Infrastructure as Code (Terraform/HCL), GitOps Automation, CI/CD, Build Management, Observability Tools, Networking, API Gateway Middleware, Security, Linux, Shell
Databases: N/A (focus on backend and infrastructure technologies)
Tools: Jenkins, GitHub Actions, NPM, Maven, PyPi, Grafana, Prometheus, Sentry, KrakenD, Kong, Tyk, Airtable, Budibase, Metabase, n8n, OpenMetaData, AWS CloudFormation, AWS Systems Manager, AWS Secrets Manager, AWS Certificate Manager, AWS Key Management Service, AWS Identity and Access Management, AWS CloudTrail, AWS Config, AWS CloudWatch, AWS Lambda, AWS API Gateway, AWS AppSync, AWS Amplify, AWS Cognito, AWS DynamoDB, AWS RDS, AWS Redshift, AWS Glue, AWS Athena, AWS QuickSight, AWS Data Pipeline, AWS Step Functions, AWS EventBridge, AWS SQS, AWS SNS, AWS SES, AWS IAM, AWS EKS, AWS ECS, AWS Fargate, AWS EKS, AWS ECR, AWS CodePipeline, AWS CodeBuild, AWS CodeDeploy, AWS CodeStar, AWS CodeCommit, AWS CodeReview, AWS Cloud9, AWS CodeWhisperer, AWS CodeArtisan, AWS CodeGuru, AWS CodePipeline, AWS CodeBuild, AWS CodeDeploy, AWS CodeStar, AWS CodeCommit, AWS CodeReview, AWS Cloud9, AWS CodeWhisperer, AWS CodeArtisan, AWS CodeGuru

📝 Enhancement Note: Progyny's technical interview process focuses on the candidate's experience with containerized environments, Infrastructure as Code, and GitOps automation. The ideal candidate will be comfortable working in a remote, collaborative environment and able to adapt to changing priorities.

💡 Interview Preparation

Technical Questions:

Technical question 1: Describe your experience with containerized environments, Infrastructure as Code, and GitOps automation. Provide examples of how you have used these technologies to support the build and deployment of solutions and services.
Technical question 2: How do you approach designing and implementing secure and scalable APIs and data services? Provide examples of your architecture and design decisions and how you have optimized performance and ensured system reliability.
Technical question 3: How do you ensure effective collaboration and communication in a remote environment? Provide examples of your communication and collaboration skills and how you have contributed to platform-wide standards and best practices.

Company & Culture Questions:

Technical question 4: How do you maintain awareness of industry trends and emerging technologies? Provide examples of how you have incorporated new technologies into your work and how you have contributed to platform-wide standards and best practices.
Technical question 5: How do you approach problem-solving and troubleshooting in a remote environment? Provide examples of how you have resolved technical issues and optimized performance and system reliability.
Technical question 6: How do you ensure the security and privacy of Progyny's APIs and data services? Provide examples of your approach to security and privacy and how you have implemented security best practices.

Portfolio Presentation Strategy:

Presentation strategy 1: Tailor your portfolio to showcase your experience with containerized environments, Infrastructure as Code, and GitOps automation.
Presentation strategy 2: Highlight your ability to design and implement reliable and secure APIs and data services, with a focus on architecture and design decisions and performance optimization.
Presentation strategy 3: Demonstrate your problem-solving skills and ability to collaborate effectively with other engineers, with a focus on contributing to platform-wide standards and best practices.

📝 Enhancement Note: Progyny's interview process focuses on the candidate's experience with containerized environments, Infrastructure as Code, and GitOps automation. The ideal candidate will be comfortable working in a remote, collaborative environment and able to adapt to changing priorities.

📌 Application Steps

To apply for this Senior DevOps Engineer – API & Business Services position at Progyny:

Submit your application through the application link provided.
Tailor your portfolio to showcase your experience with containerized environments, Infrastructure as Code, and GitOps automation, highlighting your ability to design and implement reliable and secure APIs and data services.
Optimize your resume for web technology roles, emphasizing your project highlights and technical skills.
Prepare for the technical interview process, focusing on your experience with containerized environments, Infrastructure as Code, and GitOps automation, as well as your problem-solving skills and ability to collaborate effectively in a remote environment.
Research Progyny's technology stack and company culture, with a focus on supporting the family building journey of millions of individuals.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and web technology industry-standard assumptions. All details should be verified directly with Progyny before making application decisions.

Senior DevOps Engineer – API & Business Services