About Me

Executive Summary
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.

I have over 12 years of experience as both an engineer and a leader. I have worked at a high level as an integration specialist, Product Manager, and Director for a diverse set of software vendors. This experience with a wide variety of technologies as well as experience with the integration of various information systems has allowed me to play a major role in improving and streamlining the workflow at Fortune 100 companies, top hospitals across the United States and the Department of Defense.

Contact Information
  • Fullname: Brendan O'Leary
  • Phone: (+1) 410 279-3957
  • Email: boleary (at) olearycrew (dot) com



Manager, Professional Services


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. 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.


Implementation Engineer


Implementation Engineer

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

Orbis Technologies, Inc.close

Director, Release Management

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

Applied Software, Inc.close

Director of Operations

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

Applied Software, Inc.close

Interface and Support Specialist

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

Business Network Consultingclose

Systems Technician

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

Clyde Bergmann, EECclose

IT Consultant

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.

University of Maryland, College Park

Robert H. Smith School of Business

Information Systems

Citation: College Park Scholars; Science Technology and Society


Certifications & Awards
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.

U.S. Government

TS/SCI Security Clearance

Department of Defense Top Secret Clearance. SCI Pending.



  • Languages & Frameworks 13
    Ruby on Rails
    HTML, CSS, SASS, etc.
  • Development Management 8
    Agile Scrum
    Scaled Agile (SAFe)
  • Continuous Integration 7
    GitLab CI
  • Cloud Platforms 5
    Amazon AWS
    Google Cloud Platform & GKE
    Microsoft Azure
  • Database Technology 8
  • General Technology 8
    Windows Server



Black Mirror Season 5 - DevOps

See this presentation here

Black Mirror Season 5 - DevOpsclose

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

See this presentation here

All I need to know about DevOps I learned from XKCDclose

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.

Slack App


listMe is a Slack add in used by teams all over the world. Keep lists of to-dos, discussion topics, or ideas with each person you chat with in Slack! Redesign

Web Design Redesignclose

Complete re-branding of company image, with a focus on values and mission.

Full Stack Web App

MusicTeacher.ioclose is the fastest, easiest way to get your studio online. Music teachers should focus on their students. Let us handle communication, organization & billing




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.


My Core Values &
Philosophy on Software Development

My philosophy on software development has been shaped by many well-known influencers from software and technology. I also believe there is much be be learned from others outside of the technology space. As every company becomes a software company, quality reliable software will define the next generation of businesses and social change agents.

Tough & Competent

Tough means we are accountable to our customers. We take responsibility for our software and our service, and always internalize any issue that arises.

Competent means we are always learning, always improving. We will not let small victories put us on our heels, but instead will use those victories as a launch pad to tackle harder problems.

Service before Self

We are here to serve our customers. Software is our job, not our customer's.

We will treat every interaction with the same selfless servant leadership that we would want to be treated with.

Be the change you seek

We all have responsibility to not only improve our customer's lives with our software, but improve our lives with each other.

We will all have the resourcefulness needed to focus on continuous improvement of our processes, and will take personal responsibility for the change we want to see.

Pain is temporary, suck is forever

We are an innovative company, and we will balance innovation with laying a foundation for the future.

Our decision making will be guided constantly on what's best for our customers - not what is the path of least resistance for us.