Resume

Harpreet Singh

singh.harry@gmail.com | San Jose, CA | www.linkedin.com/in/singhharpreet

SUMMARY

Entrepreneurial product leader with 20+ years of experience in building products, scaling teams, and commercializing innovation — from open source to enterprise SaaS. Co-founder of Launchable (acquired by CloudBees), where I brought AI to software testing/DevOps and led the company through seed to Series A to acquisition. Currently Co-Head of AI and VP of Product at CloudBees, shaping the company’s AI roadmap and platform integration.

A unique blend of engineering depth, product leadership, and go-to-market excellence — including enterprise selling, PLG, Customer Success, Pre-sales, and Design. Deep experience across 0→1 product development, finding product-market fit, and scaling to tens of millions in ARR. Built Open Core businesses on OSS (Jenkins), led Bitbucket Cloud at Atlassian during a critical competitive phase, and have driven multi-product strategy and interoperability in globally distributed orgs.

Led cross-functional teams globally; pitched VCs and boards; and created lasting ecosystems, including the Jenkins User Conference (which evolved into DevOps World). Trusted by investors (Battery, Unusual, 645) and executives, I’ve pitched to boards, spoken at DevOps World, and written on AI + Product + Startups. An early AI researcher (Master’s thesis on Agents) — now leading teams building with classical ML, LLMs, and exploring agentic architectures.

CAREER HIGHLIGHTS

  • Co-founder & Co-CEO, Launchable – Founded and scaled an AI-powered test intelligence startup in DevOps; secured Seed and Series A funding totaling $12M from Battery Ventures, 645 Ventures, and Unusual Ventures. Drove product vision, GTM, and enterprise sales; led the company to a successful acquisition by CloudBees in 2024.
    → Sold to enterprise customers like BMW, Poshmark, UKG, Infosys, Sony Interactive Entertainment, GoCardless — improving their time-to-test by 80%+.
  • VP of Product & Co-Head of AI, CloudBees – Leading the company’s AI platform vision post-acquisition. Spearheading GenAI, agentic, and ML initiatives to modernize DevOps workflows. Driving cross-functional team integration of Launchable into the CloudBees suite.
    → Enabling sales teams to pitch and close AI-powered solutions with customers like ARM.
  • VP Product Management, CloudBees (Earlier) – Scaled business from $0 to $50M ARR; led pivot from PaaS to Jenkins-based Open Core model. Launched Jenkins 2 OSS, DevOptics, and Jenkins-as-a-Service. Built PM org from 1 to 12 and bootstrapped the Design function.
  • GM & Head of Product, Bitbucket Cloud (Atlassian) – Drove turnaround strategy in a competitive market vs. GitHub and GitLab. Improved MRR growth, launched Bitbucket Pipes with 30+ vendors. Led strategic push to launch the Atlassian DevOps Suite with integrated workflows across Bitbucket, Jira, and Confluence.
  • Built and Scaled GTM Functions – Established Pre-sales at Launchable and CloudBees. Led Customer Success, Sales Engineering, and Marketing as co-CEO. Closed six-figure enterprise deals while also operating in PLG environments.
    → Sold to enterprise customers including Fidelity, Wells Fargo, HSBC, American Express, IRS, Delta Dental, and more.
  • Ecosystem & Community Builder – Created the Jenkins User Conference, which evolved into DevOps World, scaling from grassroots to one of the world’s largest CI/CD conferences.
  • Global Team Leadership – Managed cross-functional teams across US, Europe, Japan, and Australia. Led managers in Product, Sales, Design, and Marketing functions.

EXPERIENCE

CloudBees – VP of Product & Co-Head of AI
Jul 2024 – Present | San Francisco Bay Area

  • Driving CloudBees’ AI strategy post-acquisition of Launchable, aligning product, engineering, and GTM to enable adoption of AI-powered solutions.
  • Built a dedicated Agentic AI team and incubated a PM function focused on GenAI and MCP-based automation across CloudBees platform.
  • Led cross-functional integration of Launchable, including team onboarding, product alignment, and GTM unification.
  • Empowering sales and marketing teams to sell AI-driven capabilities into enterprise accounts such as ARM.

Launchable Inc. – Co-Founder & Co-CEO
Sep 2019 – Oct 2024 | San Francisco Bay Area

  • Founded and scaled an AI-native test intelligence platform; raised $12M from top-tier VCs (Battery, 645, Unusual).
  • Led product, GTM, and business strategy; built the initial product and scaled through PMF to enterprise revenue.
  • Ran M&A process end-to-end, culminating in a successful acquisition by CloudBees.
  • Built and led functions across Product, Sales, Marketing, Customer Success, and Pre-sales; recruited and mentored executive team. Also led Product Marketing end-to-end — crafting core messaging, positioning, and GTM narratives that shaped Launchable’s category story and enterprise outreach.

Atlassian – GM & Head of Product, Bitbucket Cloud
Jul 2018 – Sep 2019 | San Francisco Bay Area

  • Led strategic reboot of Bitbucket Cloud during a high-stakes competitive phase versus GitHub and GitLab.
  • Integrated Bitbucket with Jira, Confluence, and Opsgenie as part of a unified Atlassian DevOps suite.
  • Launched Bitbucket Pipes with 30+ vendor integrations; drove growth in MRR and pipeline efficiency.
  • Managed cross-functional leadership team spanning PM, Strategy, Product Analytics, and Design.

Sun Microsystems – Product Manager, Java EE / GlassFish / Jenkins (Hudson)
Jun 2000 – Jan 2010 | Santa Clara, CA

  • Transitioned from engineering into product management, owning the roadmap and go-to-market strategy for GlassFish, the open source Java EE application server.
  • Led the design and implementation of Java EE Security as part of the engineering team prior to PM role.
  • Identified and championed Jenkins (then Hudson) as a strategic asset in the emerging CI market.
  • Took Jenkins to market as part of the open source product strategy — laying the foundation for its commercial evolution at CloudBees.

Persistent Systems – Software Engineer
May 1997 – Aug 1998 | Pune, India

  • Designed and implemented a high-performance caching layer for ad-serving infrastructure.
  • Gained early exposure to startup environments and product-centric engineering, sparking long-term entrepreneurial interest.

EDUCATION

Santa Clara University – MBA, Finance, Entrepreneurship, General Management
University of Cincinnati – MS, Computer Science (Thesis in AI Agents)
Pune Institute of Computer Technology – BE, Computer Engineering

SKILLS & CERTIFICATIONS

Leadership & Product: Product Strategy, Product-Led Growth (PLG), GTM Strategy, Multi-Product Platforms, Ecosystem Building, Open Core Models, Board & Investor Communication
AI/ML Expertise: LLMs, Classical ML, Agentic AI Systems, RAG Patterns (Strategic), AI-Powered Product Development
Execution & Growth: Fundraising, PMF Discovery, Enterprise Sales, Customer Success, Pre-sales, Design Leadership
Certifications: Agile Certified Product Owner, Pragmatic Marketing (Foundations, Focus, Build), Agile Scrum Master

THOUGHT LEADERSHIP & SPEAKING

  • Author of the Substack AI + Agents + Entrepreneurship, covering trends in GenAI, product innovation, and startup execution.
  • Speaker at JavaOne, DevOps World, Jenkins User Conference, and multiple industry podcasts on topics ranging from product-led growth to AI-powered DevOps.
  • Frequent guest on founder-focused podcasts and panels discussing category creation, GTM playbooks, and AI disruption in software engineering.