Brendan O'Leary

Experienced Servant Leader & DevRel Expert

Summary

Over my 15+ years in software, I have led critical roles during GitLab's growth from Series C to IPO and directed ProjectDiscovery's Series A shift from open source to commercial viability. My experience spans venture-backed and bootstrapped businesses, with a strong foundation in leadership and developer tools. I have managed key projects, showcasing entrepreneurial flair and an in-depth understanding of Sales, Marketing, and Product dynamics. My success merges commercial objectives with open source values, reflecting my passion for transparent, iterative collaboration.

Experience

ProjectDiscovery

December 2022 - Present

Head of Community

As Head of Community and a key member of the executive team at a Series A startup, I led the growth and engagement of the community around ProjectDiscovery's innovative cybersecurity open source projects. My role focused on expanding the community while ensuring the well-being of our contributors. By balancing commercial goals with genuine community engagement, I worked to maintain the vibrancy and strength of our open source community as the business evolved — all while contributing to the commercial success of ProjectDiscovery.

GitLab

October 2017 - December 2022

Senior Developer Evangelist

Connect with other developers, contribute to open source, and share work externally about cutting-edge technologies on conference panels, meetups, in contributed articles and on blogs. Interact with developers across the globe at conferences as well as online, and co-create with the open-source community on the most impactful projects in the ecosystem. Focus on generating awareness about GitLab by rolling up my sleeves, contributing to the ecosystem, and enabling others to become evangelists outside the company as well.

Senior Product Manager

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.

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.

Slim.ai

February 2021 - February 2024

Advisor

As an advisor to Slim.ai, I advised the CEO and marketing team on building a robust and sustainable open source community composed of contributors, users, and advocates. By implementing strategic community engagement practices and ensuring alignment with Slim.ai's goals, I aimed to enhance collaboration, drive growth, and ensure the long-term success of the Slim.ai open source ecosystem.

CNCF

June 2020 - December 2022

Cloud Native Computing Foundation
Governing Board Member

The CNCF Governing Board (GB) is responsible for marketing and other business oversight and budget decisions for the CNCF. The GB does not make technical decisions for the CNCF, other than working with the TOC to set the overall scope for the CNCF. Served on the Compensation Committee.

Orbis Technologies

October 2016 - October 2017

Director, Release Management

Build a strong DevOps-focused group within Orbis, a government and commercial contractor. Supported large programs for delivery to top-tier Fortune 100 companies and the US Department of Defense, including the 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.

June 2006 - October 2016

Director of Product

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.

Education

University of Maryland

May 2008

BS, Business Administration: Information Systems

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

Certifications & Memberships

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

Skills

  • Languages & Frameworks - JavaScript, Node.js, Golang, Java, Metor.js, ASP.NET, Agile Scrum, Python, HTML
  • Product & Engineering Management - Git, SVN, GitLab, BitBucket, GitHub, Kanban, Scaled Agile (SAFe)
  • Continuous Integration - GitLab CI/CD, Jenkins, Ansible, Hygieia, Docker Cloud, Kubernetes, Helm
  • Cloud & Infrastructure - AWS, Azure, Google Cloud, Digital Ocean, Heroku, Terraform, Ansible, Puppet, Chef
  • Security & Compliance - OWASP, NIST, ISO 27001, SOC 2, GDPR, HIPAA, PCI DSS
  • Database Technology - PostgreSQL, Microsoft SQL, MarkLogic, MongoDB, Redis, MySQL, FoxPro
  • General Technology - GSuite, Word, Excel, PowerPoint, Linux, SSH, REST, Security