top of page
1jon_ariel_best.jpeg

Industry Contributions

Work Experience

High-energy, customer-centric people leader that has been successful in a variety of technical and leadership roles over the last 15 years. First and foremost, I am a company leader; I transcend silos: I have led product management, design, software engineering teams and marketing and sales efforts in public and private organizations. I thrive in high-growth, fast-paced environments, and lead teams through challenges & changes with transparency, candor, urgency, and purpose.

Experienced communicating with executive leadership and Board of Directors at public & private organizations, adapting teams through stages of growth and profitability, and driving impact cross-functionally with senior leadership in GTM, S&M, R&D, M&A and G&A on many initiatives.

I also serve the community by being a mentor and advisor to aspiring talent and innovators.

Professional Background

Jan 2025 - Present

Senior Director, Product Management - Inorganic Growth & Market Evangelism

Rapid7

rapid7-black-orange-logo-04-2022.png

Lead company M&A and partnership strategy. Meet regularly with founders to evaluate tech & teams. 

Create internal & external GTM content, craft compelling positioning narratives, and enable sales and channel on them.

Accountable for land & expand transaction count and ARR goals.

2024 - Jan 2025

Senior Director, Product Management - Innovation (Exposure Management)

Rapid7

rapid7-black-orange-logo-04-2022.png

Head of planning & launching Rapid7's Command platform, and Exposure Command product family; our dominant land motion.

Responsible for driving Product, GTM, and GTC strategy, in addition to being the M&A product leader and core deal team member of Rapid7's acquisition of Noetic (CAASM).

Accountable for land & expand transaction count and ARR goals.

Results include generating the largest post-launch pipeline in company history with $40m+ within 3 months. Exceeded 2024 ARR goal by 237%, and transaction count by 137%.

July 2022 - August 2023

Senior Director, SOAR Business Leader

Rapid7

Tampa, FL

rapid7-black-orange-logo-04-2022.png

Responsible for the success of Rapid7's insightConnect product line, serving over 2000 customers and generating over $20m in ARR within 2 years.

Leading & managing a P&L for a ~100 person organization of engineering, design, product, and operations.

Results include a 40% growth in revenue, 6% increase in CRR, and improvement of Expenses to Revenue (E:R) by 73%. 

Transformed the engineering organization with new leadership, a higher talent bar, accountability around deliveries, & improved quality standards led to more customer needs met and improved confidence from the sales floor.

Achieved an 88% Employee Retention Rate (14% increase); 10% above the company average.

Scaled engineering team to Europe, hiring 28 engineers within 6 months, a growth of 50% by creating a strong relationship with Talent Acquisition and rethinking the way we hire and attract talent. Raised talent bar led to only 1 attrit in 2 years post hiring, and met more customer expectations.

Increased investment in quality & operations which resulted in a 80% decrease in service degradations improving our overall customer experience.

August 2020 - July 2022

Director, SOAR Engineering

insightConnect-black-logo-06-2022.png
August 2018 - August 2020

Director, Integration Engineering

Responsible for the development of 3rd party integrations across the Rapid7 portfolio of of products. Led engineering, product management, roadmap, and strategy.

Partnered regularly with our Strategic Alliances team on high impact integrations from top partners.

July 2015 - August 2017

Head of Security & Alliances

Komand

komand-logo.jpeg

Founding security member of Komand, an early-stage Boston based cybersecurity startup that was acquired by Rapid7 in 2017.

I wore many hats but effectively was the Field CTO, Security Leader & Integration leader where I worked with customers and technical partners to build & sell our technology while also building out a secure platform and security automation use-cases, while also technically contributing to the product itself.

Hired a team of ~30 engineering and technical writer contractors to develop marketing content, integrations, thought leadership and use-cases.

Engaged with customers on pre-sales and post-sales engagements to create value. Traveled to onsite prospect locations to sell to customer leadership. 

June 2013 - August 2020

Chief Executive Officer

Draconyx

draconyx-hero-foreground.png

Owner of a boutique cyber security and IT consulting company that provided a variety of services but specialized in information security training and had customers in the Fortune 500.

2013 - 2015

Security Engineer

Performed cybersecurity at scale, defending one of the world's fastest supercomputers.

One of the first teams to implement security automation and ChatOps, necessary to handle volume of alerts.

Performed network traffic & log analysis, incident response, deployment and development of monitoring & IR tools.

Member of the official Bro NSM team, funded by the National Science Foundation, focused on video and conference training.

National Center for Supercomputing Applications

ncsa_vertical_logo.png
2011 - 2013 

Head of IT & Information Security

Touch of Class

New-TOC-Logo-TOC-Maroon-web.png

Led IT department for a retail company that had 4 locations, a call center, and online store.

 

Instituted information security policies and achieved PCI DSS compliance. Developed & operationalized a vulnerability management & network security monitoring program. Performed incident response and trained department in security practices.

Managed VoIP & telephony software for call center, and network devices connecting 4 locations.

Unix system administration of Linux, FreeBSD, AIX, and MacOS servers and workstations with LDAP, internal mail servers, network storage, customer management and ordering systems, and more.

Painting Wall

Advisory & Mentorship

I love contributing back to the community and helping others. I do pro bono / volunteer work as well as having paid advisory positions.

Screenshot 2025-03-08 at 11.49.24 AM.png

Tampa Bay Wave

Pro bono mentor of founders in the Wave accelerator. 

Screenshot 2025-03-08 at 11.47.11 AM.png

Hack.Diversity

Pro bono mentorship of diverse talent in software engineering & cybersecurity fields

productpass.png

Product Pass

Serve on the Advisory Board

https://www.productpass.ai

Certifications

Connectd Board Advisor

Scrum Master

GIAC Reverse Engineering Malware (GREM)

GIAC Intrusion Analyst (GCIA)

Wireshark Network Analyst

Berkeley Software Distribution (BSD-A) - Associate

Linux Professional Institute,

LPIC-1

CompTIA Linux+

CompTIA A+

CompTIA Network+

CompTIA Security+

USA Powerlifting Club Coach

ARRL Technician Class License

PADI Advanced Open Water Diver

USA Weightlifting Club Coach

Awards & Publications

Received Rapid7's Never Done award in 2024 for successful launch of Exposure Command.

xsede-full-color-1024x388.png

Short book from Syngress Press,

December 1, 2015.

Peer reviewed research published in the Proceedings of XSEDE, July, 15, 2015 St. Louis, MO with colleagues.

2600.gif

Article published in 2600: The Hacker Quarterly, Spring 2015 issue.

HIGH 5 Employee Award - ISLET, 2014

NCSA Technical Excellence Award - for scalable logging infrastructure, 2014

securewvlogo_horizontal_on_black-300x70.png

Capture the Flag Winner, Black Badge Recipient. Hack3rCon, 2011

Professional Organizations

I have a passion for teaching & learning from others; as a result I have been involved in many orgs but the following I created or led directly.

© 2024 by Ashton Schipp.
Powered and secured by Wix

Location

Tampa, FL

Email

jon[at]jonschipp.com

Follow

  • substack
  • GitHub
  • LinkedIn
  • Instagram
bottom of page