Director, Web Infrastructure
Freedompay
Other Engineering
Philadelphia, PA, USA
Posted on Apr 7, 2026
The FreedomPay Commerce Platform is the technology of choice for many of the largest companies across the globe in retail, hospitality, lodging, gaming, sports and entertainment, foodservice, education, healthcare and financial services. FreedomPay’s technology has been purposely built to deliver rock solid performance in the highly complex environment of global commerce. The company maintains a world-class security environment and was first to earn the coveted validation by the PCI Security Standards Council against Point-to-Point Encryption with EMV standard in North America. FreedomPay’s robust solutions across payments, security, identity and data analytics are available in-store, online and on-mobile and are supported by rapid API adoption. The award winning FreedomPay Commerce Platform operates on a single, unified technology stack across multiple continents allowing enterprises to deliver a consistent, repeatable experience on a global scale. FreedomPay is a fast paced, high growth company with a great culture with competitive benefits and compensation with a business casual atmosphere.
We are seeking an experienced Director of Web Infrastructure to lead and grow our Platform, Web Infrastructure, DevOps, Site Reliability, Release Engineering, and Infrastructure Architecture capabilities. The right candidate finds real satisfaction in making complex, mission-critical systems more reliable, more automated, and faster to deploy. Our environment is a pragmatic mix of established on-premises infrastructure and a growing Kubernetes footprint, and the right candidate will bring a track record of delivering results with the tools at hand.
About the Role
This position participates in an engineering escalation on-call rotation.
This position is based in the Philadelphia area with a hybrid schedule. Fully remote arrangements may be considered for exceptional candidates, with occasional travel to Philadelphia.
You’ll manage day-to-day operations of the DevOps and Release Engineering teams while working closely with Site Reliability, Infrastructure Architecture, and numerous development teams across the organization. The position is nominally 50/50 hands-on technical work and people management.
This is a global operation — our infrastructure spans multiple regions and time zones, and the pace of delivery reflects that. The right candidate will bring the flexibility and commitment that a 24/7 payment platform demands.
Primary Responsibilities
- Serve as a trusted operational right hand to the VP — owning execution, anticipating needs, and driving priorities forward
- Day-to-day management of DevOps and Release Engineering teams
- Work closely with Site Reliability, Infrastructure Architecture, and numerous software development teams to drive cross-functional initiatives
- Provide hands-on support to teams during release preparation, deployment execution, and post-release stabilization
- Ensure efficient delivery of initiatives from inception through production deployment and beyond, with a strong emphasis on release readiness and cross-team coordination
- Own production support escalations and drive rapid resolution across teams
- Continuously improve intra-team and inter-team processes and workflows
- Facilitate collaboration across the organization and promote leadership priorities and vision
- Provide direct, hands-on, expert-level technical assistance as needed
- Perform additional related tasks as assigned
- After-hours support for any production issue escalation as needed, in an on-call rotational basis to provide after-hours support
Required Background & Experience
- Bachelor’s degree, graduate degree, or equivalent experience
- Extensive, recent experience in a mature, heavily Microsoft-oriented environment
- Experience in a high-volume, global service provider or payment processing environment
- Demonstrated history of self-directed learning — someone who independently seeks out knowledge, builds new skills without being told to, and doesn’t wait for formal training to close gaps
- Proven ability to get up to speed quickly in large-scale, legacy-rich environments
- Strong sense of ownership and service — takes pride in making their leadership and their teams more effective
- Excellent communication and organizational skills
- Strong problem-solving skills and a bias toward practical, proven solutions
Required Technical Skills
- Deploying and managing large-scale, high-volume production .NET applications with zero-downtime requirements
- Advanced Windows Server / IIS deployment, configuration, and administration
- Kubernetes (AKS) deployment, configuration, and administration
- Azure cloud platform experience
- Azure DevOps
- Git
- NGINX
- Cryptography & Certificate management
- Proficiency with AI-assisted development and automation tools
- Solid understanding of DNS, HTTP/HTTPS, load balancing, TCP/IP routing and switching
Preferred Technical Skills & Experience
- Software development experience
- Octopus Deploy
- Argo CD / Argo Rollouts
- Dynatrace (or equivalent APM platform at scale)
- PowerShell
- SQL
- Redis
- F5
- OpenShift
- Apache Kafka
- RabbitMQ
- Database deployment automation
- Experience integrating QA test automation into CI/CD
- Additional Experience, a Plus:
PCI policies and best practices, AI/ML, Service catalog implementation and management, documentation automation, Snowflake
As the fastest growing commerce company in the industry, we offer the opportunity for tremendous upward mobility within the company as well as development and professional growth opportunities. FreedomPay's fulltime roles provide exceptional benefits including medical, prescription, dental and vision coverage, Life Insurance, Retirement Plans with company match, commission sharing plan, flexible hybrid working environment, and great parental and other leave programs. All positions must be able to successfully pass a background check as well as a credit check.