Brendan O'Leary

Experienced Servant Leader & DevOps Expert

Over my 14 years in software development, I have:

  • Managed software product lines and product managers, including dozens of products from idea through to market
  • Fervently advocated for the user experience at all times
  • Obtained and honed expert skills in managing all aspects of application development; including but not limited to - product design, user experience, product-market fit, and technical implementation and delivery
  • Proven to be highly motivated, results-oriented, and gained extensive experience in working with clients, customers, and end users of information system solutions


  GitLab, Inc.

Product Management & Professional Services

October 2017 — Present

Heavily involved in the hyper-growth of a VC-backed startup - seeing the valuation grow to over a billion dollars. As such, I've had a lot of opportunities to contribute throughout the company (and seen it grow from 100 employees to over 1000 worldwide and 100% remote).

Most of my time has been spent in product management and in starting and growing our professional services offerings.

Sr. Solutions Manager

Act as product manager for GitLab’s services organization. Define, scope, and prioritize GitLab’s services and training offerings, including persona and market segmentation analysis, offering definition, scope, and pricing.

Sr. Product Manager, Verify (CI)

Directly responsible for driving product direction for GitLab’s Verify stage (covering CI and automated testing). Engaged with stakeholders, including internal customers, external Fortune 100 customers, and open source users and contributors. Evangelize and provide thought leadership across the DevOps tool space, including engaging with analysts and presenting results and vision.

Manager, Professional Services

Lead a team of Implementation Engineers to deliver a high level of service to GitLab's large and strategic Fortune 500 clients. Responsible for worldwide delivery of implementation, migration, integration, and training services to a diverse set of customers. Created DevOps Transformation engagements to help customers level-up their software delivery across many verticals and industries.

  Orbis Technologies, Inc.

Director, Release Management & Software Quality

October 2016 — October 2017

Build strong DevOps focused group within Orbis, a government and commercial contractor. Supported large programs for delivery to top-tier Fortune 100 companies and US Department of Defense, including United States Special Operations Command (SOCOM). Led adoption of continuous integration and continuous delivery methodologies both within Orbis and within the DoD itself.


Director of Product

June 2006 — October 2017

Focused on helping ASI grow their business in the healthcare technology field. Involved in managing all aspects of the company from support to implementation to new and current product development. Also placed in charge of many enterprise-level project management functions such as business development with well respected software vendors in the healthcare industry.

  Clyde Bergemann EEC

IT Consultant

June 2001 — June 2006

Worked as a direct report to the CIO of EEC. Worked in all areas of IT including troubleshooting, networking, and enterprise server management. Helped to migrate a NT 4.0 domain to a 2003 Sever environment . Supported various departments including the engineering and sales divisions including end users as well as server support.


Languages & Frameworks

  • JavaScript, Node.js
  • Java
  • Agile Scrum
  • Python

Product & Engineering Mgmt

  • Git
  • GitLab, BitBucket, GitHub
  • SVN
  • Kanban
  • Scaled Agile (SAFe)

Continuous Integration

  • ​GitLab CI/CD
  • Jenkins
  • Ansible
  • Docker
  • Kubernetes

Cloud Platforms

  • ​Heroku
  • Amazon AWS
  • Google Cloud Platform
  • Microsoft Azure
  • Firebase

Database Technology

  • PostgreSQL
  • Microsoft SQL
  • MongoDB
  • Redis
  • MS FoxPro

General Technology

  • Word
  • Excel
  • PowerPoint
  • Linux
  • SSH
  • REST


University of Maryland

BS, Business Administration
Information Systems
Graduated May 2008
College Park, MD

Robert H. Smith School of Business
Citation: College Park Scholars, Science Technology and Society


  • Certified Agilist (SAFe 4.0)
  • Top Secret Security Clearance (interim)
  • CompTIA Security+ Certification