Tampa, FL · board advisor & director · startup founder

Cybersecurity leader who actually builds things.

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.

See the work View CV
Jon Schipp Jon as the Ric Flair of Cybersecurity
a.k.a.
The Ric Flair of Cybersecurity
15+ yrs · Rapid7 / Komand (founding) / NCSA Supercomputing / Draconyx (founder) / The Cyber Toolchain (founder) / AI Toolchain / Gartner EAP Leader
01 / ABOUT

Tech leader, husband, and waterman.

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."

50+
Industry tutorials & technical writings
40+
Conference & user-group talks
10+
Major product & tool launches
3
Peer-reviewed publications
02 / SELECTED WORK

Products I directly led, owned, or shipped.

full portfolio →
Surface Command
RAPID7 · ASM

Surface Command

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.

insightConnect
RAPID7 · SOAR

insightConnect

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

Komand
STARTUP · ACQUIRED

Komand

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

Quick Actions
RAPID7 · PLATFORM

Quick Actions

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

ISLET training terminal
OPEN SOURCE

ISLET

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

mal-dnssearch terminal output
GITHUB · 100+ FORKS

Open-source toolkit

A long trail of practical tools — Nagios plugins, network IOC search, packets-per-second utilities — used across many organizations.

03 / HOW I CREATE VALUE

Let's build something great together.

①

Customer-driven product strategy

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.

②

Planning & execution leadership

Direct leadership of 100+ person teams, as well mobilizing cross-functional groups that don't report to me, executing on shared business plans.

③

Talent acquisition & management

Scaled global teams in high-growth environments while raising the talent bar and protecting culture.

④

Inorganic growth (M&A)

On both sides of the table — deal-team stakeholder, due-diligence lead, lead negotiator, and M&A committee member at a public company.

⑤

Board advisory & governance

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.

⑥

Cyber, music & fitness

Domain depth in IT & cybersecurity, plus competitive coaching in strength sports and years on stage playing guitar.

04 / BEYOND THE WORK

The whole person.

The things that keep me sharp, humble, and a little dangerous.

Waterman
🌊

Waterman

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

Metal guitarist on stage
🎸

Metal guitarist

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

Strength coach
🏋️

Strength coach

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

Hacker roots
💾

Hacker roots

Slackware in 8th grade, CTF black badge, published in 2600: The Hacker Quarterly.

05 / ASK ME ANYTHING

Talk to my AI.

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.

Powered by Delphi · responses reflect my own thinking

Open full conversation ↗
$ ./reach-out.sh

Advisory · board · building together.

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.

Schedule a meeting → [email protected] ✉
GitHub LinkedIn
Jon Schipp · Tampa, FL Brand kit → we are never done.