Matthew E. Porter is an entrepreneur, endurance athlete, and MS advocate. He is the Senior Partner and Co-Founder of Eonova, a growth advisory firm built by entrepreneurs for entrepreneurs, and serves on the boards of multiple companies, from high-growth startups to established enterprises. Porter founded Contegix in 2004, growing it from a bootstrapped startup to an industry leader in managed hosting, cloud computing, and Atlassian services. Under his leadership, Contegix expanded to over 350 employees and $100M in revenue before being acquired by Valiantys in 2024. He has also held executive roles at EmpowerMe Wellness, Clayco, and Invisibly and was inducted into the John Cook School of Business Smurfit-Stone Entrepreneurial Hall of Fame at Saint Louis University. Recognized for his leadership, he has been featured in the New York Times, Wall Street Journal, and Forbes and was named to Saint Louis Business Journal’s “30 Under 30” and “40 Under 40” lists.
Beyond business, Porter is an ultramarathoner who channels his endurance running into advocacy for multiple sclerosis, a disease he battles himself. Since taking up trail running in 2010, he has completed numerous 100-mile races, including Leadville Trail 100, and has raised funds for MS research through his races. In 2022, he and a fellow MS warrior ran 103 miles nonstop to Missouri’s state capital, Jefferson City, to engage policymakers in the fight against MS. Porter lives in Weldon Spring, Missouri, with his wife and three children, guided by his family’s mission: “We have a debt to those before us and an obligation to those after us. We maximize life and potential through heart, intelligence, and grit. We focus on our bond. We do all of this together because we are always stronger together. Mostest.”
Technical debt has been a known challenge since Ward Cunningham introduced the term in 1992. However, focusing solely on technical debt ignores other, equally damaging forms of debt that accumulate within organizations—cultural debt, leadership debt, process debt, and data debt.
As companies navigate AI adoption, remote work challenges, and economic shifts, these hidden debts create bottlenecks, inefficiencies, and retention issues that technology leaders must address.
This session will expand the conversation beyond technical debt, providing a strategic framework for identifying, measuring, and mitigating most forms of organizational debt.
Key Takeaways:
Why technical debt is only part of the problem – and how other debts silently undermine growth.
The impact of cultural, leadership, and process debt – with real-world examples.
How today’s challenges (AI, remote work, and economic pressures) accelerate hidden debts.
A framework for identifying and managing organizational debt before it becomes a crisis.
Actionable steps for tech leaders to build a sustainable, high-performing organization.
The best technical leaders do not just solve problems—they fall in love with them. Great coders embrace complexity, break down challenges, and iterate toward solutions. Great leaders must do the same—but instead of debugging code, they debug systems, organizations, and strategies.
In this session, we will explore the Leadership Paradox: The higher you rise, the bigger and more complex the problems become—and the longer they take to solve. Drawing from Gerald Bell’s research, we will discuss why organizations grow to the size of their senior leader and why scaling leadership capacity is essential for scaling a company.
Through real-world examples and actionable frameworks, we will cover:
Why today’s most pressing leadership challenges—AI, cybersecurity, technical debt, and talent retention—require long-term thinking.
How to transition from solving immediate technical problems to driving strategic, high-impact solutions.
The four-step framework for breaking down, iterating, and scaling leadership problem-solving.
Why the most successful organizations embrace problems as opportunities for innovation rather than roadblocks.
Key Takeaway:
The biggest problems yield the greatest opportunities—but only if leaders develop the mindset and discipline to tackle them strategically. If you are a technical leader looking to elevate your leadership capacity and scale your organization, this is a session you cannot afford to miss.
Two and a half days of insightful sessions, inspiring ideas, and meeting your peers. Learn the skills and methods that will take your organization to the next level.
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