Software, Strategy, and Service: The Multifaceted World of Mike Couvillion

Jason Malki
SuperWarm
Published in
4 min readOct 5, 2023

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I had the pleasure of interviewing Mike Couvillion, an experienced senior executive with over 28 years of experience in the software engineering space. He is the CEO of his own consulting company, AlexaGuru, where he collaborates with Private Equity firms to offer Executive Coaching and Due Diligence for M&A activities. Mike has partnered with esteemed organizations such as Insight Venture Partners, Paine-Schwartz, Riverside, Silverlake, Battery, and, most recently, Vista Equity Partners, where he was recognized as one of their Outstanding Executive Leadership Team Members. Throughout his career, Mike has overseen and nurtured world-class engineering teams worldwide, some with as many as 300 developers. In the past 12 years, he has played a pivotal role in building three distinct software companies, each culminating in a successful exit. His expansive experience spans various sectors, including real estate, vehicle web services, oil and gas analytics, learning management systems, security, and Human Resources Technology. As a proud USAF veteran with 8 years of service, Mike is passionately involved in the nonprofit sector, assisting elite veterans as they transition from military life to the civilian business world.

How did you break into your tech career?

My background is in computer science and mechanical engineering. In college, I developed a point-of-sale system for video stores, marking my first commercial success. I served in the Air Force for 8 years, with the last two years heavily focused on deployable network systems. By the mid-90s, I had become intrigued by the burgeoning “Internet” and recognized its potential. I began my post-military career with a small tech company specializing in systems engineering and networking systems, primarily involving Sun Microsystems. Later, I transitioned back into the software realm, joining Symantec. There, I leveraged the security expertise I had acquired during my military service.

What is it that excites you about what you’re building in your current role?

As a Chief Technology Officer I enjoyed many years of working with teams and solving problems. Now, I get great satisfaction from coaching and mentoring up and coming executives. I also enjoy advising firms that may not have a strong technical presence as they look to acquire software companies. I advise on how to strategically leverage technology as a revenue generator like you would sales/marketing. I also can lead traditional technical due diligence teams.

My other hat is that of Chief Operating Officer for my wife’s luxury home interior design company. She built it from the ground up and grew it to the point where she needed more mature processes and disciplines to help run her teams of employees and clients. I helped do that and I’ve been amazed at how many parallels there are in re-designing a home and re-designing software. In that role I handle the finance and marketing as well as human resources. And, yes, sometimes I’m still asked to fix the wifi.

What has been your biggest challenge in your current role?

On a personal front, the challenge was transitioning from being the “answer guy” to the “question guy”. As an engineer, there’s an innate desire to fix what’s broken. However, as a leader, it’s crucial to trust your team and avoid micromanaging. Your role evolves into one of support, providing resources rather than always supplying the answers; it’s more about asking the right questions.

Professionally, a significant challenge is encountering executives who perceive technology as a “necessary-evil-cost-center” rather than recognizing it as the force multiplier for revenue that it truly is. It’s astounding how many times I’ve been hired by a CEO to help shape strategy, only to find in our first meeting that no one from the Product or Tech department is present — even in software companies. I recall a CEO remarking, “Well, it’s because my CTO doesn’t think strategically.” If that’s the case, the onus is on the CEO for appointing someone with a limited vision to lead. This often stems from the CEO’s misconception that technology plays a minor role in the company’s operations.

If you had to share, “words of wisdom,” with a Tech Executive who’s starting their career, what would they be?

Here are a few:

  • Do not fall in love with your shiny new tech. No one will buy your product just because it has a killer new framework. Use the best, most efficient tool for solving the problem at hand.
  • Learn to speak the language of finance and sales. They don’t think or talk like you. Learn what is important to them and make your case supporting their goals.
  • Don’t over elaborate to the other execs. We tend to want to impress others with technical details. Stop doing that. If you can’t boil down the problem and recommendation into 5 or 6 bullet points then you haven’t analyzed the issue enough and are likely too into the weeds. When you are in the weeds you aren’t looking long term and that is why the CEO isn’t inviting you to the strategic table.
  • Don’t sugar coat or lie about bad news even if it is your fault. Nothing will torpedo your career faster than getting a reputation for not being honest.

How can our readers follow you on social media?

My LinkedIn is https://www.linkedin.com/in/couvillion/

This was very insightful. Thank you so much for joining us!

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Jason Malki
SuperWarm

Jason Malki is the Founder & CEO of SuperWarm AI + StrtupBoost, a 30K+ member startup ecosystem + agency that helps across fundraising, marketing, and design.