Mike Flouton

CMO & CPO | $5.2B in Exits | ex-GitLab, ex-Barracuda | DevOps geek building Crash Override | SF ➔ BOS

Greater Boston

About

I seek to transform growth-stage SaaS organizations into market leaders by blending hands-on product innovation with strategic vision and strategy. Engineered four exits, creating billions of dollars in shareholder value. I started as a software engineer, became a product leader who built categories from scratch, and ultimately a VP at a public company responsible for a multi-billion dollar product portfolio. This 'full-stack' operational experience, from writing the first line of code to managing a P&L at scale, gives me a unique lens as an early-stage investor, where I've built a portfolio of over 25 B2B SaaS startups. I partner with founders at the earliest stages, helping them navigate the complex journey from product to profit. I am now seeking to leverage this blend of hands-on building and strategic investment experience.

Experience

  • Chief Marketing Officer at Crash Override
    Jan 2026 - Present · 7 mos

    Crash Override is the data plane for software in the AI era. We sit underneath the toolchain, tag every artifact at build time with a signed record of what it is and where it came from, and serve tailored answers off a single graph for engineering, security, and compliance. We make AI provenance, software compliance and incident response trivial. I owned CI/CD at GitLab. Customers continually asked us to explain their pipelines and help them migrate off Jenkins. We had no answer. I'm thrilled to finally be able to give them one. Backed by Google Ventures, SYN, and Blackstone.

  • Managing Partner and Founder Advisor at Boxford Capital
    Jan 2017 - Present · 9 yrs 7 mos

    25+ companies as an active angel investor and advisor. Provide strategic guidance to a portfolio of early-stage founders on fundraising, pitch deck refinement, and go-to-market validation as a mentor for a global remote accelerator program. My investment thesis focuses on founder-led B2B companies with deep technical moats in AI, Security, DevTools, and Enterprise SaaS. I provide hands-on support post-investment, specializing in: - Pre-seed/Seed Product Strategy & Roadmap Development - Go-to-Market & Early Customer Acquisition - Founder Mentorship & Leadership Coaching - Executive Team Buildout

  • VP, Product Management at GitLab
    Feb 2023 - Oct 2025 · 2 yrs 9 mos

    Product leader for source code management (AI Code Suggestions, AI Code Review), agile planning and CI/CD (AI Root Cause Analysis). 2x Gartner MQ Leader for DevOps Platforms, 2x Forrester Wave Leader for Software Delivery Platforms, Gartner MQ Leader for AI Code Assistants. • 46% y-o-y SaaS growth, 31% total company growth, 15% non-GAAP operating margin • Set product strategy that led to $4.2 billion in valuation growth • Lead ~30 headcount product organization • Leader of Create group, AI features in developer workflow • Leader of CI/CD group, which owns AI based pipeline root cause analysis • Oversaw launch of GitLab Dedicated, GitLab Dedicated for Government (FedRAMP ATO) • Cultural transformation to focus on outcomes over activity, reinvention of OKR process (All public numbers from earnings transcripts)

  • VP, Product Management at Barracuda
    Sep 2017 - Jan 2023 · 5 yrs 5 mos

    Led product organization for $300mm email security business. More than doubled top line over three years (25% CAGR), grew SaaS segment at 76% CAGR. More than doubled win rate against primary competitor (Mimecast). 2x Forrester Wave leader (2021, 2019), SE Labs Best Email Security Solution (2021), SC Magazine Best Email Security Solution, Best Use of AI/Security (2022, 2021), CRN Best Email Security Product (2020). • Led 25 headcount org, including product managers, data scientists and awareness training business unit • Rebooted email protection business (innovation, pricing, packaging, messaging) leading to peak >130% SaaS growth • Pioneered use of AI/ML including NLP to spot impersonation attacks, creating ICES category • Incubated automated AI based classification system for user-submitted phishing reports • Introduced Product Led Growth (PLG) motion to accelerate acquisition, cross and up sell • Overhauled NPI/PLC process, standardized across product teams • Introduced cross-portfolio product OKR framework • 2021 worldwide Barracuda team trivia champion

  • VP, Worldwide Product Marketing at BAE Systems Applied Intelligence
    May 2011 - Aug 2016 · 5 yrs 4 mos

    As VP of Product, Digital and Content Marketing at SilverSky, I architected a complete business turnaround, leading to the company's successful ~$270mm acquisition by BAE Systems. Owned product marketing, messaging, digital marketing, analyst relations and demand generation strategy. - Led the marketing and product relaunch, rebuilding the go-to-market organization from the ground up and driving double-digit growth while maintaining profitability. - Owned the end-to-end GTM function, including product marketing, demand generation, brand, and communications for 15+ SaaS offerings. Following the acquisition, I was retained and promoted to lead global product marketing for the combined $750M commercial business unit at BAE Systems. - In this expanded role, I directed the go-to-market strategy for a 4,000-person organization, owning the positioning and messaging for 20+ offerings across 7 lines of business. - Transformed the tactical product marketing team into a strategic function, bridging the gap between product and sales to drive growth.