A. Kai Armstrong

Principal Product Manager with 10+ years of experience driving product strategy, development, and growth across enterprise DevSecOps platforms, managed services, and SaaS products. Proven track record of launching products that generate millions in revenue, from startup exits to enterprise-scale platforms. Expert in cross-functional leadership, data-driven decision making, and building products that delight customers while meeting business objectives.

Experience

Principal Product Manager | GitLab / 2019 - Present

Currently leading platform strategy and Agentic AI initiatives for GitLab’s collaborative code review workflows; supporting organizational development best practices, approval and compliance workflows, and developer collaboration. Grew code review workflow MAU by 27% while simultaneously pioneering AI product initiatives for code review experiences and expanding platform reach to 200K+ users across multiple developer tools beyond GitLab’s web application. Continuing to drive strategic product evolution through market intelligence and cross-functional collaboration.

  • Lead GitLab’s agentic AI strategy, having driven the launch and roll-out of Duo Code Review, GitLab’s agentic code review experience, that now contributes over 30% of weekly active AI users and continues establishing next-generation capabilities for the enterprise AI platform
  • Continuously evolve developer workflow efficiency through intelligent merge request homepage serving over 450,000 daily active users with action-focused prioritization, validated through ongoing UX research and iterative improvements leading to an almost 10% decrease in time to begin a code review
  • Drove 40% performance improvement and 65% memory reduction for large merge requests by analyzing data to establish size benchmarks, benchmarking against competitors, and setting clear engineering targets
  • Pioneered GitLab’s AI thought leadership by recognizing market shifts and moving the team to deliver early AI/ML-powered use cases. Supported this with a series of blog posts to establish a vision for AI-powered code review
  • Built comprehensive instrumentation across 70+ unique metrics enabling data-driven insights and strategic decisions for improving code review workflows for all users
  • Led business case and acquisition for GitLab CLI from concept to 112% YoY growth and GitLab VS Code extension, establishing foundation for GitLab’s future Agentic AI expansion efforts

Senior Product Manager | Hostway / 2016 - 2019

Led a product portfolio of cloud-based solutions, generating over $15MM ARR. This portfolio included hosting platforms for Magento ecommerce stores, web-based email, and a suite of collaboration tools for web conferencing, document collaboration, and cloud storage. I drove the go-to-market strategy for diverse channels, including retail SMBs and Fortune 500 partners, who white labeled and resold these services as part of their business internet offerings.

  • Launched Managed Magento product with go-to-market strategy and roadmap, achieving nearly $250k annual run rate
  • Conceptualized and launched Managed Microsoft Office 365 offering that was trending toward $100k+ first-year revenue
  • Introduced new Anti-Virus/Anti-Spam solution to 1.2M+ mailbox users, improving user satisfaction and saving $120k annually in licensing
  • Crafted and delivered executive-level communications, including board meeting materials and weekly health reports, to align senior leadership on product performance and strategic roadmaps
  • Managed critical vendor relationships for products and services essential to SMB offerings; negotiating new agreements for cost savings and business continuity, and establishing new partnerships to expand our reach

Product Implementation Manager | Gray Digital / 2015 - 2016

Led SMB and Large Health Organization web projects from inception to completion, spearheading new product offerings for small business growth objectives while improving WordPress maintenance procedures to increase quality and reduce developer time.

Director of Products | Pressable / 2010 - 2015

Wore multiple hats to grow the startup from inception to $X million in ARR, positioning the company for a successful exit to Automattic, the industry-leader behind WordPress.com.

  • Implemented self-service billing based on customer feedback, reducing billing support requests by 90%
  • Managed agile development process that increased monthly recurring revenue by 20%+
  • Built Enterprise customer relationships through continuous communication ensuring exceptional service delivery

Education

MBA, Stetson University
BS Hospitality Management (Minor: Computer Science), University of Central Florida

Skills

Strategic: AI Product Strategy & Agentic AI Development, Developer Platform & Ecosystem Strategy, Cross-Functional Team Leadership, Enterprise Partnership Development, Business Case Development & Financial Analysis, Compliance & Security Controls, GTM Enablement

Technical: API Design & Developer Experience, Performance Analysis & System Architecture, Data Analytics & Metrics Instrumentation, A/B Testing & Experimentation, DevSecOps Platform Integration, Full-Stack Development (JavaScript, Python, Ruby, Go), Infrastructure as Code & Container Orchestration, Open Source Contribution