For founders, boards, and investors scaling cybersecurity and tech companies. As an operator who's owned P&Ls, led M&A, and shipped category-defining products, I help teams find product-market fit, build better products, and create lasting differentiation — advising on product, GTM, and leadership.


Hi, I'm Jon. I love cybersecurity, building SaaS products, and exploring the ocean. I believe mission, culture, and leadership are everything — and I lead authentically, with urgency, candor, and a strong sense of purpose.
My path started early: I was running Slackware Linux in the 8th grade, which opened the door to my first role as a Unix sysadmin. Before that, I toured the Midwest playing guitar in a metal band — where I learned resourcefulness, storytelling, sales, and how to energize an audience.
Over 15+ years I've built on-prem and SaaS products, founded and operated a boutique consulting company, sat on both sides of acquisitions, owned P&L at a public company, and led teams across product, engineering, UX, operations, marketing, and sales.
"I'm not here for mediocrity. I'm an agent of change — and we are never done."
Led the product & GTM launch of Rapid7's flagship exposure-management platform. Became the company's dominant land-and-expand offering, aligned to Gartner's CTEM framework, and earned a Leader position in the new Exposure Assessment Platform Magic Quadrant.

Incubated, proved, and led product, GTM, and business development for the launch of Rapid7's Cyber GRC solution — unifying Security Operations and GRC in a single platform to improve cross-functional efficiency and align security outcomes with compliance, and created an audit partner program. Announced via the Early Access Program and a HITRUST assurance partnership.

2024 launch of Rapid7's attack-surface management product — the only solution of its time to unify internal (CAASM) and external ASM with risk-based VM.

Ran the full SOAR business — ~100 people across eng, design, product & ops. Grew to $20M+ ARR and cut churn 4% in two years.

Founding security member of a Boston cybersecurity startup acquired by Rapid7 in 2017. Led integrations, use-cases & sales engineering.

Embedded investigative & response tools across multiple Rapid7 products to drive adoption and surface platform value in-context.

Authored an open-source tool for teaching Linux & security tooling at universities. Co-authored a peer-reviewed paper at XSEDE.

A long trail of practical tools — Nagios plugins, network IOC search, packets-per-second utilities — used across many organizations.
I am relentlessly customer-driven — more than 1,000 customer conversations across my years in product. Deep understanding of customer needs, business drivers & market dynamics, to test, develop, and ship products aligned to them.
Direct leadership of 100+ person teams, as well mobilizing cross-functional groups that don't report to me, executing on shared business plans.
Scaled global teams in high-growth environments while raising the talent bar and protecting culture.
On both sides of the table — deal-team stakeholder, due-diligence lead, lead negotiator, and M&A committee member at a public company.
Board advisor and director material — public-company M&A-committee experience, plus regular analyst briefings with Gartner, Forrester & IDC. Serve on the Tampa Bay Wave Accelerator and Maro advisory boards and mentor founders.
Domain depth in IT & cybersecurity, plus competitive coaching in strength sports and years on stage playing guitar.
The things that keep me sharp, humble, and a little dangerous.

On the water as much as I can be. The ocean is where I reset and stay humble.

Toured the Midwest in a metal band. Storytelling and energizing a room started here.

USA Powerlifting & Weightlifting club coach. Where I learned grit, commitment, and delayed gratification.

Slackware in 8th grade, CTF black badge, published in 2600: The Hacker Quarterly.
Curious about my take on cyber, product leadership, M&A, or building a career in cyber? My AI clone is trained on my work and experience — ask it anything, anytime.
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Open full conversation ↗Three ways to work together: advisory (product, GTM, leadership), board (advisor or director), and building (co-founding or early-stage). If you're a founder, board, or investor scaling a cybersecurity or tech company, let's talk.