Sessions · Advisor session
How to sell to the CIO
Monday, May 18, 2026 · 12–1 PM PDT
This session has ended.
About this session
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
Hosting this session
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.r
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.r
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.r
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.r
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.
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Next step
Have a question behind the session?
Share what you’re working through. If your company qualifies, we’ll reply personally within 24 hours.
For companies that have raised at least $1M from venture firms.