Director, Web Infrastructure

FreedomPayPhiladelphia, PA
Hybrid

About The Position

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. 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.

Requirements

  • 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
  • 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

Nice To Haves

  • 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
  • PCI policies and best practices
  • AI/ML
  • Service catalog implementation and management
  • documentation automation
  • Snowflake

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

Benefits

  • medical
  • prescription
  • dental and vision coverage
  • Life Insurance
  • Retirement Plans with company match
  • commission sharing plan
  • flexible hybrid working environment
  • great parental and other leave programs
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