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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.

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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.

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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

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Lead portion of company M&A and partnership strategy. Meet regularly with founders to evaluate tech & teams, due diligence, negotations and alignment.

Bring new products & features to market
​​, derived from partnership opportunities.

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

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Accountable for land & expand transaction count and ARR goals.

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2024 - Jan 2025

Senior Director, Product Management - Innovation (Exposure Management)

Rapid7

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Head of planning & launching Rapid7's Command platform, and Exposure Command product family; our dominant land motion. Solution achieved 2nd place Leader position in Gartner's EAP Magic Quadrant.

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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).

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Accountable for land & expand transaction count and ARR goals.

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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

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

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

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

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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.

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

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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.

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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

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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.

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

July 2015 - August 2017

Head of Security & Alliances

Komand

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

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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.

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

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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

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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.

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

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

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

National Center for Supercomputing Applications

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2011 - 2013 

Head of IT & Information Security

Touch of Class

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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.

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

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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.

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Tampa Bay Wave

Pro bono mentor of founders in the Wave accelerator. 

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Hack.Diversity

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

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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.

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​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.

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

HIGH 5 Employee Award - ISLET, 2014

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NCSA Technical Excellence Award - for scalable logging infrastructure, 2014

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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.
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Location

Tampa, FL

Email

jon[at]jonschipp.com

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