About Me

I revel in solving the soft problems in the tech space. Motivating teams and bringing DevOps culture to light the dark corners of software delivery. Currently I am an Engineering Leader using DevOps methods and collaboration to generate crossfunctional productivity. My passion is unblocking and keeping teams motivated to develop new and stable product on-time and on-budget. With over 20 years of Industry experience including Quality Assurance, Development, Release Management, and Application Architecture

Contact Details

Cædman Oakley
Redwood City, California
(415) 630-3722

Castlight Health

Director of Resilience Engineering Current

Joined Jiff (acquired) as Director of Engineering I/O, responsible for moving to continuous releases and developing tight linkage between engineering and infrastructure. Moved from a 100% downtime release to 0 downtime releases.

  • Increased availability from 95.4% to 99.9975% in less than 3 years.
  • 25 reports over 3 teams. Manager for offshore and local groups.
  • Moved Wellness platform to 0 downtime releases.
  • Worked with engineering to move legacy systems to containerized deploys.
  • Integrated Infrastructure teams from 2 separate companies.
  • Managed VMWare Datacenter and AWS infrastructure to deliver hybrid solution.
  • Adopted up-to-date Monitoring and Dashboarding for data-driven problem resolution.
  • Reduced remote team attrition from 25% YoY to 0%.


Sr. Engineering Manager 3/16 - 10/16

Hired to manage and develop cloud infrastructure for Augmented Reality platform. Improved delivery pipeline of applications reducing time for internal delivery from 2 weeks to 1 day. Enabled yum-backed repositories for internal package delivery and dependency management

  • Managed for local and remote groups.
  • Initiated continuous delivery model adoption.
  • Completed full hiring within 2 months.


Sr. Engineering Manager 11/11 - 3/16

Joined as Release Manager, responsible for legacy releases and metrics tracking. Automated and decentralized release to generate scalability and became Engineering manager for Platform As A Service.

  • 28 reports over 7 teams. Manager for offshore and local groups.
  • Architected Continuous Delivery project.
  • Reduced Legacy stack rollbacks from 1 in 20 days to 1 in 850 days.
  • Search Product delivered on schedule with 0 outages since delivery.
  • Reduced deploy times - 90 minutes per service to 20 minutes.
  • Reduced regression test overhead -140 hours to 65 hours per cycle.
  • Developed infographic webapp for QA Metrics - MTBF up 20-30%
  • Developed Release candidacy tooling - release outages down 30%


Sr. Software Engineer 9/09 - 11/11

  • Cross-functional HTML5 Subject Matter Expert.
  • Co-ordinated CSS, JS Minification, HTML optimization across 3 teams.
  • Decreased retail SSL portal pageload 16%, increasing conversion 11%.
  • Reduced merge times from 2 days/sprint to 2 hours via branching.

Previous Positions

  • Limelife - Sr. Software Engineer
  • Meevee - Software Engineer
  • First Data Utilities NZ - Software Engineer
  • Southern Cross NZ - Senior QA Lead
  • GFG Group NZ - Senior QA Developer
  • Greenwood Technology - QA Developer
  • Microsoft (MSTV) - SDET (Project Lead)
  • Network Associates (McAfee) - SDET (Team Lead)


Currently I am involved in DevOps Management. I have experience in SDLC Process implementation, Continuous Integration, Continuous Deployment and Continuous Delivery. I have been integral in Quality Assurance, and am familiar with SCRUM, Kanban, and LEAN methodologies.

  • Ruby
  • JavaScript
  • HTML5
  • Java
  • Git
  • Jenkins
  • AWS Deployment
  • Adobe CS Suite


University of Southampton

BA (Hons) in French and Computer Science (Computational Linguistics) 1994

UPPA, France

DEUG (Equivalency) in Informatique 1993

UPPA, France

Licence (Equivalency) in Lettres Modernes 1993

DevOps Days - your local DevOps conference

Looking for the place to find information about what's going on in the world of Devops? Try DevOps Days.


  • Cads ... makes sure that his teams have clear and measurable goals, that they use automation to increase their ability to scale up the amount of systems they support, and he communicates the business goals the team is facing so that team members can be more effective in making choices that solve both the long term problems and the immediate firefighting tasks. He emphasizes strong communication by team members with both fellow team members and other parts of the company, and this helped our team be very effective even though we were spread over three offices and had a quarter of the team fully remote.

    Joe Block - SRE @Castlight Health
  • When we worked together Cads was a hard charging customer advocate who always completed tasks assigned on time, often going above and beyond expectations. Cads was a trustworthy coworker both ethical and conscientious in interactions with others. Even if he was a lone voice, Cads would clearly speak truth to power. But once a decision was made, he lined up with the team to get the job done.

    Dan Piton - IT Manager @Humana
  • "Gets things done", is in one phrase how I would describe Cads.I have had the opportunity to report to him while working at Ooyala, in his position as Senior Engineering Management, and my first impression after I explained the struggles I was going through, was actually great; quoting him "remember you're no longer working with systems, but with people".
    Although things like this may seem obvious, guidance and consistency make him a great mentor in addition to a very trustable and consistent manager, a pleasure to work with, always smiling and open to listen to what you have to say, providing leadership and opening clear channels of communication.
    I'd work again with Cads at any time, and would highly recommend him as a Senior Engineering Manager.

    Gabriel Medina - Manager @Ooyala
  • Cads ran the release and tools team for me at Ooyala. He did a fantastic job of managing both an onshore and an offshore team and was the primary evangelist in the company for driving us to a true CICD process. Cads is someone that you can count on to effectively lead his teams and to get the job done.

    Rick Pittenger - SVP Engineering @Ooyala
  • Cædman is a hard worker who performs his tasks quickly and throughly. He is passionate, dedicated, works well in a group and just generally amazes me by bring 110% to the table in the hopes of making the product be the best it can possibly be.

    Stephen Warren - Product/Project Manager
  • I worked with Cads for almost two years at Ooyala. Cads did a phenomenal job stabilizing Ooyala's release process, developing and driving stability and quality metrics, and helping communicate effectively both within the org and with external partners. Cads hands-on coding and integration skills made him an effective change-agent building tools and working with engineering teams to define and implement process. Cads managed to keep calm and carry on during incidents and under extreme pressure. His can-do attitude and special brand of humor made him a natural leader and a huge asset for the entire team. I would be delighted to get the opportunity to work with him again in the future.

    Nimrod Hoofien - Head of Product Engineering @Gusto

Contact Form

I value data-driven results and motivation. Using this model to accelerate the feedback loop, and drive Continuous Delivery is at the heart of how our industry moves. But this is useless without correctly targeting the skills and abilities of resources. Do you want to know more about driving a culture of learning and collaboration? Drop me a line.