18
May
Mon
in-person
How to sell to the CIO, John Matthews, J Leslie and Co. Consulting
How to Successfully Sell to a CIO
Selling to a CIO is one of the hardest things a founder can do. They're balancing legacy systems, security mandates, internal politics, and a hundred competing priorities — and they've seen every pitch before.
In this Expert Session, John Matthews - a seasoned CIO with decades of experience on the buying side — will help you understand exactly how CIOs think, what they care about, and what it actually takes to earn their trust and close the deal.
Come with your live-fire challenges. Every attendee gets time to work through their specific situation and walk away with concrete, actionable insights.
What you'll learn:
- How to lead with business outcomes, not features
- How to position yourself as a partner, not just a vendor
- How to navigate internal politics and stakeholder complexity
- How to reduce the perceived risk of buying from you
Speaker
“
John Matthews
Fractional CIO & Advisor. J Leslie and Co. Consulting.
John Matthews is an accomplished executive leader with over three decades of experience scaling fast-growth companies and driving IT and security operations. As a former Chief Information Officer (CIO) at ExtraHop Networks and F5 Networks, John has consistently delivered results, helping organizations grow from start-up to multi-million-dollar exits.
With a proven track record of increasing operational efficiency, enhancing security, and aligning technology with business objectives, John has led high-performance teams that support everything from employee engagement to revenue operations.
Collaboration is a key pillar of John’s leadership philosophy—both internally with cross-functional teams and externally with stakeholders and vendors. He focuses on building technical strategies that meet business needs while fostering a culture of transparency, trust, and growth.
John’s results include scaling ExtraHop from $30M to a $900M exit and leading F5’s worldwide technology operations, including an Oracle ERP implementation that transformed global business processes.
John also serves as a front-line spokesperson, having presented at industry-leading events such as RSA and BlackHat, and has been featured in outlets like CIO Magazine and TechTarget. His leadership extends beyond technology, with a focus on developing long-tenured teams that are motivated and outcome-driven.
In addition to his executive roles, John has consulted for major organizations including Microsoft, Adobe and Apple, advising on technology strategy, security, and operations. He brings a unique blend of business acumen and technical expertise, making him a sought-after consultant for companies looking to drive results and secure their technology infrastructure.
01
all founders,
not just ceo
People inclined to be Founders are a rare breed, and are hard to spot in society. We welcome ALL Founders, regardless of role, and generate proprietary profiles for every member so you can easily find your next team member or co-Founder.
02
current founders
Regardless of where you are on your journey, Founders share a unique set of challenges. Hiring, leadership, managing investors, developing products, handling customer issues, external communications, etc. This community exists to amplify your success.
03
TRANSITIONING FOUNDERS
So you’ve founded at least one company, and now you’re looking to refine your next great idea or find the perfect co-founder. Share and learn from a wide array of talented Founders in your area.
04
CURIOUS FOUNDERS
Congratulations! You’ve found success as a Founder and are now getting curious about doing it again. Now you need to find the right idea and co-founder to excite you. Share your wisdom and passion while forming new bonds within the startup ecosystem in your area.
To Pre-Qualify for participation, please fill out an application
Apply Now