Change is constant

I’ve spent most of my career inside organizations at moments when something important about technology needed to change.

For more than 20 years, I’ve looked after architecture, product and engineering, infrastructure, cybersecurity, modernization, M&A, and technology strategy. I’ve served as CTO and interim CTO, built and reorganized teams, inherited difficult systems, made investment decisions, and lived with the results.

Since 2021, I’ve mainly advised investors buying software and technology-enabled businesses. Nearly 80 engagements, ranging from buy-side and sell-side diligence to portfolio value creation, integrations, organizational assessments, and interim technology leadership. I led most of them. Many were founder-owned companies where the person who built the system was still running it.

Seeing that many companies in a relatively short period gives you a different perspective.

Every company has obstacles

Technical debt, security gaps, aging systems, nascent processes, organizational tension, and ambitious roadmaps not rooted in fact. The harder question is: how much of it matters?

Will it interfere with the investment thesis? Will it slow growth? Is there a large expense coming after close? Is the current CTO capable of leading the company through the next stage? Is management underestimating the problem? Is an advisor making too much of it? Those are the questions I spend most of my time answering.

I’m energized by situations where the answer is not obvious. Usually, several plausible explanations exist, with evidence pointing in different directions. I like getting to the root of the symptoms, identifying the real constraint, and reducing a complicated situation to a few important decisions.

Sometimes the answer is uncomfortable

The technology leader who brought the company to $10M ARR might not be the right person to get them to $100M ARR. Post-close integration may end up much more complicated than assumed at closing because diligence missed a key component. On closer review, the proprietary data may not be the AI disintermediation moat we thought it was. Sometimes the technology is scalable and well-built, and the recommendation is to leave it alone.

My years as an operator matter here

I know what recommendations look like from the other side of the table. Real companies have budgets, deadlines, personalities, customers who cannot be disrupted, and teams that must keep running while changes are being made. For two decades, I’ve worked with executive leadership and their teams to solve technology-centric problems together. It’s still the most fulfilling work I do.

Today, most of my work connects investment decisions with what actually happens inside the company. I advise buyers during diligence, help translate what we learn into post-close priorities, and work with portfolio leadership when technology becomes central to the value-creation plan. I work with deal teams on underwriting questions, with CEOs and CTOs on operating issues, and with investors when a technology problem becomes material enough to require a clear point of view.

Expert view

Having a senior technology partner advising through the hold period and not just contracted, ad hoc, during diligence helps companies run smoothly even when a deal team or investor is out of their area of expertise. Larger firms employ a technology operating partner for exactly this. Unfortunately, most acquirers are not large enough to justify one and end up making technology decisions alone, without an expert in the room.

If you are looking at a company, or you own one and something isn’t adding up, I’m reachable at thomkaleta at gmail dot com and on LinkedIn.