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Cybersecurity leader focused on building & advising startups on product, GTM, & leadership


My Top Cigars of 2025
Top 10 list of the best cigars I smoked in 2025
Jon Schipp
Dec 31, 20253 min read


A Practical Guide to Running Effective Product Pilot Programs
A guide to running product pilot programs to validate and test hypotheses.
Jon Schipp
Dec 13, 202514 min read


Generating Demand for a New Product Launch
Methods for generating demand prior to launching a new product.
Jon Schipp
Nov 29, 20254 min read


It’s a Sprint Not a Marathon: The Case for High Intensity Work
High intensity work often leads to greater accomplishments, deeper purpose, and ultimately greater job satisfaction. We will explore this in more detail
Jon Schipp
Nov 26, 20254 min read


Recovery from High Intensity Work
Tactics & alignment for recovering from high-intensity work.
Jon Schipp
Nov 26, 20253 min read


GRC Analysts are Starved for Data
GRC & SecOps teams are fragmented and silo'd leading to disruptions, inefficiencies, and inhibiting business impact. But it doesn't have to be this way!
Jon Schipp
Nov 26, 20254 min read


Turning Visibility Into Defense: Connecting the Attack Surface to the Detection Surface
An organization’s Attack Surface and its Detection Surface are inextricably linked. Learn how to use these foundational concepts to drive better security outcomes.
Jon Schipp
Nov 25, 20257 min read


PMs! Your Network Matters for Product Discovery
A quick, practical guide on building your network for better product discovery!
Jon Schipp
May 18, 20257 min read


My Journey in & out of the Hacker Community
My journey from an angsty teen to a cybersecurity professional
Jon Schipp
May 17, 202519 min read


SaaS is Cloud: A Look at SSPM
I talk to a lot organization's that forget that SaaS is Cloud. Some of their most important business assets (e.g. data) reside in...
Jon Schipp
Feb 2, 20254 min read


My Favorite Cigars & the Journey to Smoke
When we moved to Tampa almost 3 years ago I wasn't anticipating that I would pick up a new vice. Despite that introduction, I actually...
Jon Schipp
Dec 30, 20246 min read


Techniques to Hire Faster, Part 1 Recruitment
Learn techniques to hire candidates more quickly!
Jon Schipp
Dec 18, 20246 min read


Product Due Diligence Guide for M&A
This document outlines how to perform product due-diligence work for an acquistion.
Jon Schipp
Dec 12, 202416 min read


The Ric Flair of CyberSecurity
Coining of Ric Flair of Cybersecurity
Jon Schipp
Dec 10, 20241 min read
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