Resume

Raul Santos

Director of Engineering – New York, NY Languages: English (Native), Spanish (Native)

Engineering executive specializing in infrastructure, DevOps, and platform engineering. Proven track record building and scaling high-performance engineering teams, establishing engineering culture, and delivering reliable systems that power millions of users. Deep technical expertise combined with strategic leadership and cross-functional collaboration.

Experience

Director of Engineering

Peloton Interactive – New York, NY (2017 - Present)

Lead engineering organization responsible for infrastructure and platform capabilities powering Peloton’s global connected fitness ecosystem serving millions of members. Drive technical strategy, organizational growth, and operational excellence across multiple engineering teams.

  • Provide strategic direction for engineering teams delivering critical infrastructure, platform services, and DevOps capabilities
  • Build and scale high-performing engineering teams through strategic hiring, mentorship, and career development programs
  • Partner with C-level executives, product, and business stakeholders to align technical investments with company objectives
  • Establish and evolve engineering culture focused on reliability, scalability, operational excellence, and continuous improvement
  • Own technical roadmap and architecture decisions for infrastructure supporting global scale connected fitness platform
  • Drive cross-functional initiatives spanning engineering, product, and operations organizations

Senior Manager, Engineering

Peloton Interactive – New York, NY (2016 - 2017)

Expanded leadership scope to manage multiple engineering teams and drive cross-functional infrastructure initiatives during period of rapid company growth.

  • Managed and grew engineering teams from 5 to 15+ engineers, establishing scalable processes for team expansion
  • Led technical planning and roadmap development for infrastructure initiatives supporting 10x user growth
  • Drove adoption of engineering best practices, SRE principles, and DevOps culture across engineering organization
  • Established on-call rotation, incident response procedures, and operational excellence standards

Manager, Engineering

Peloton Interactive – New York, NY (2015 - 2016)

Transitioned into engineering management, building Peloton’s first dedicated DevOps and infrastructure engineering team.

  • Built and led team of DevOps and infrastructure engineers from ground up
  • Established team processes, sprint planning, and delivery frameworks balancing operational work with project delivery
  • Balanced hands-on technical contribution with people management and strategic planning
  • Implemented hiring processes and onboarding programs for infrastructure engineering roles

Lead DevOps Engineer

Peloton Interactive – New York, NY (2014 - 2015)

Led the DevOps engineering function, designing and implementing the automation and infrastructure practices that supported Peloton’s rapid growth from startup to scale-up.

  • Architected and maintained AWS cloud infrastructure supporting Peloton’s connected fitness platform
  • Designed and implemented CI/CD pipelines, deployment automation, and infrastructure-as-code practices
  • Mentored junior engineers and established DevOps standards, best practices, and documentation
  • Served as technical lead for infrastructure projects and architectural decisions

DevOps Engineer

Peloton Interactive – New York, NY (2013 - 2014)

Joined Peloton as early infrastructure hire to build DevOps practice from scratch, bringing infrastructure automation and reliability engineering to fast-growing consumer technology company.

  • Implemented infrastructure-as-code practices using Ansible, Terraform, and AWS CloudFormation
  • Built comprehensive monitoring, alerting, and incident response tooling and processes
  • Collaborated with development teams to improve deployment velocity, reliability, and developer productivity
  • Established foundation for scalable infrastructure supporting company’s growth trajectory

Lead Engineer

Oscar Health – New York, NY (2012 - 2013)

Led engineering initiatives at technology-driven health insurance startup, driving infrastructure and platform reliability for mission-critical healthcare systems.

  • Led cross-functional engineering projects focused on infrastructure scalability and platform reliability
  • Mentored engineers and contributed to team growth, technical standards, and engineering culture
  • Drove technical decision-making for key platform components supporting health insurance operations
  • Established operational best practices and incident response procedures

Senior Engineer

Oscar Health – New York, NY (2011 - 2012)

Took on expanded technical ownership of critical infrastructure systems supporting health insurance platform.

  • Owned and improved core infrastructure and platform services ensuring high availability
  • Contributed to architecture decisions and technical strategy for scaling healthcare platform
  • Partnered with cross-functional teams to deliver product features with infrastructure reliability
  • Implemented monitoring and alerting systems for production environment

Engineer

Oscar Health – New York, NY (2010 - 2011)

Joined early-stage health-tech startup to build technology platform powering innovative health insurance products.

  • Developed and maintained infrastructure and platform services supporting insurance operations
  • Participated in on-call rotations and incident response for production systems
  • Contributed to improving engineering processes, tooling, and deployment practices
  • Collaborated with product and operations teams to deliver customer-facing features

Client Platform Engineer

Cornell University – Ithaca, NY (2009 - 2010)

Managed client platform engineering and Mac infrastructure within major research university IT environment.

  • Managed and supported Mac computing platforms across university departments and research labs
  • Implemented automation for device management, software deployment, and configuration management
  • Provided technical solutions for large-scale endpoint management supporting thousands of users
  • Developed custom tools and workflows for Mac administration at institutional scale

Engineer

BBH USA – New York, NY (2008 - 2009)

Delivered technology solutions and infrastructure support at global creative advertising agency.

  • Supported and maintained technology infrastructure for creative agency environment
  • Implemented solutions to support business operations and creative production workflows
  • Provided technical support for Mac and mixed-platform environments

Additional Experience

  • OK Magazine (2008) – Technology and infrastructure support for major media publication
  • Ogilvy (2007 - 2008) – IT support role at global advertising network
  • Geek Squad (Best Buy) (2005 - 2007) – Computer technician providing hands-on customer technology support

Technical Skills

Infrastructure & Cloud: AWS, Cloud Architecture, Infrastructure-as-Code, Configuration Management

Video & Streaming: Video Delivery Infrastructure, Streaming Protocols, Encoding & Transcoding, CDN Architecture, Live Streaming Platforms

DevOps & Automation: CI/CD Pipelines, Deployment Automation, Shell Scripting, Ansible

Platform Engineering: macOS/Apple Platform Management, Endpoint Management, Monitoring & Observability

Leadership: Team Building, Hiring & Mentoring, Technical Strategy, Cross-functional Collaboration, Agile/Scrum

Education

Bachelor of Arts, Latin American Studies State University of New York at New Paltz – 2003-2008

Open Source & Community

Active contributor to the open source, Mac administration, and video technology communities with 2,000+ followers and 500+ professional connections. Member of the autopkg organization. Notable projects include infrastructure automation tools and AWS integration utilities.

  • GitHub Profile – 53+ public repositories
  • Member of @pelotoncycle and @autopkg organizations
  • GitHub Developer Program Member
  • Active member of video-dev.org Slack community
  • Host of Video Tech NYC meetup group
  • Active contributor to MacAdmins Slack community
  • Regular participant in Mac, DevOps, and video technology community events

Speaking & Conferences

Conference Participation:

  • MacDevOps:YVR – Annual DevOps and Mac administration conference in Vancouver
  • MacSysAdmin – European Mac systems administration conference
  • MacAdmins Conference at Penn State
  • Regular participant in local DevOps and infrastructure meetups in New York City

Community Contributions:

  • Technical presentations at MacAdmins community events
  • Active participant in MacAdmins Slack community discussions
  • Open source project maintainer and contributor
  • Mentorship and knowledge sharing in the Mac platform engineering community

Contact