Brendan O'Leary

Experienced Servant Leader & DevOps Expert

Skilled in managing application development. Experienced with Agile Scrum, Kanban and Scaled Agile practices. Zealous advocate for the user experience. Highly motivated, results oriented, vast experience in dealing with clients, customers, and end users of information system solutions.

See my work


Over my 12 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 / Manager, Professional Services

March 2018 - Present

Lead a team of Implementation Engineers to deliver a high level of service to GitLab's large and strategic Fortune 500 clients. Work together with the other managers within the Customer Success organization to help execute on strategies and vision with the Director, WW Customer Success. 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.


GitLab / Implementation Engineer

October 2017 - March 2018

Act as the technical representative leading the direct interaction with the customer’s personnel and project teams by rolling out the best practices. Helped the customer to faster benefit from the Gitlab solution for business value. Collaborate with product management and engineering teams on the actual field experience through customer engagement and implementations.


Orbis Technologies, Inc. / Director, Release Management

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.


Applied Software, Inc. / Director of Operations

June 2008 - October 2016

Involved in managing all aspects of the company from support to implementation to new and current product development. Led implementation of Agile Scrum methodology, increasing engineering productivity by 400%. Responsible for many enterprise-level project management functions such as business development with well respected software vendors in the healthcare industry.


Applied Software, Inc. / Interface and Support Specialist

June 2006 - June 2008

Worked with ASI’s software package for mammography information management. Worked with centers and large hospitals to fit our software into their clinical workflow. Managed various projects to automate workflow tasks with HIS, RIS and other hospital systems.


Business Network Consulting / Systems Technician

July 2003 – August 2004

Designed, implemented, and maintained a variety of Windows networks, servers, workstations, and networking equipment for a variety of clients. Consulted with various businesses on ways to improve their business model based on business requirements and technological needs.


Clyde Bergmann, EEC / IT Consultant

June 2001 – August 2006

Worked as a direct report to the CIO of EEC. 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 engineering & sales divisions.

Education & Certifications


University of Maryland, College Park
Robert H. Smith School of Business

May 2008

B.S. in Business Administration
Information Systems
Citation: College Park Scholars; Science Technology and Society


Scaled Agile, Inc.
SAFe Agilist

The Scaled Agile Framework is a proven, publicly available framework and website for applying Lean and Agile practices at enterprise scale.


Security+ Certification

Security+ is compliant with ISO 17024 standards and approved by the US DoD to meet directive 8140/8570.01-M requirements.


U.S. Government
TS/SCI Security Clearance

Department of Defense Top Secret Clearance. SCI Pending.

Contact Me

Speaking & Talks

Black Mirror Season 5 - DevOps

Black Mirror presents a haunting view of how modern technology places society a “minute away” from a dystopian future. DevOps and those of us that practice it find ourselves in a similar situation - partially mature technologies whose implications we don’t yet fully understand. Heartbleed, Equifax and now Meltdown & Spectre can make us feel like there is no escaping this dark future. But just as Black Mirror examines the extremes of these concepts as a canary in the mine shaft for society, we too can carefully employ practices that will prevent season 5 from featuring Site reliability engineer, DevOps engineer, or CISO characters.

In this talk, we'll learn how to use the powerful concepts and tools behind DevOps for good... with great power comes great responsibility....but also great opportunity to do good for our businesses, each other and our world. By working together with product, business, and external teams; embedding security into how we operate; and measuring everything we do we can empower our teams to thrive.

All I need to know about DevOps I learned from XKCD

XKCD describes itself as “a webcomic of romance, sarcasm, math, and language.” What if it is more? What if XKCD and it’s creator Randall Munroe have slowly been revealing what software development, DevOps and team collaboration are all about.

In this talk, we’ll take a look at some recurring themes in XKCD comics - and how they hit home with recurring themes in DevOps. From regular expressions, vim vs. emacs to user experiences so bad...they are literally a joke XKCD finds ways to express simply the thoughts we’ve all had. We will examine these comics for their deeper meaning (deeper even than just the tooltip text Randall leaves behind) and learn from them how to make better software.

Closer to the Code: Speed up development by focusing on CI

When we want to improve the speed and performance of our applications, we often look at moving processes “closer to the processor.” But, what if the speed we want to improve is our cycle time when shipping customer value? The answer is similar - move the processes required to ship closer to the code. When we invest in continuous integration (CI), we can plateau once we have the code building and tests running. However, to deploy effectively, we need to embrace code review, dependency assurance, security scanning and performance metrics for every commit. To accelerate this cycle, all of these required processes must happen closer to the code. Learn how Kubernetes and GKE - paired with GitLab CI/CD - make this promise of CI possible, all without writing a bunch of brittle code glue.


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A passion of mine in my spare time is amatuer photography. Taking pictures of landscapes or my kids... I pride myself in having an eye for design.