Why Most Incentive Plans Fail—and How Thoughtful CEOs Get Them Right

My Guest I’m joined this week by Stacey Carroll, who has spent substantially her entire career leading HR organizations across a wide array of companies, with a specific focus on compensation & benefits. She has also spent the past 14 years leading HR Experts on Call, a company she founded where she acts as anContinue reading “Why Most Incentive Plans Fail—and How Thoughtful CEOs Get Them Right”

Installing an Operating System in Your Business: Lessons from Real EOS Implementations

My Guest Over the past handful of years, there has been substantial growth in the number of companies who have decided to implement formal “operating systems” to govern certain strategic and operational decisions within their businesses. I implemented EOS (or “the Entrepreneurial Operating System”) in my own company beginning in 2015, and we continued toContinue reading “Installing an Operating System in Your Business: Lessons from Real EOS Implementations”

Leverage: Doing More With Less

Listen to this Blog Post “Give me a lever long enough, and a place to stand, and I will move the earth.”– Archimedes “Leverage” is one of those concepts that tends to be interpreted as being more complex than it actually is. The simplest way to define leverage might be “the ability to do moreContinue reading “Leverage: Doing More With Less”

Five Ideas That Every CEO Should Know

Listen to this Blog Post What follows are five unrelated thoughts on how to lead and grow a healthy and vibrant company. None of them are long enough to justify a stand-alone blog post, but all of them are important enough to highlight for current and aspiring CEOs. (1) Crafting an Effective Company-Wide Bonus PlanContinue reading “Five Ideas That Every CEO Should Know”

Answers to Recurring FAQs from Current and Prospective Searchers

Listen to this Blog Post Over the course of many years speaking with current and prospective searchers on a near-daily basis, I’ve come to appreciate that many searchers understandably tend to have very similar questions and areas of uncertainty. Indeed, in most instances, I had these very same questions and areas of uncertainty myself priorContinue reading “Answers to Recurring FAQs from Current and Prospective Searchers”

What I’d Change if I Could Re-Do the First 90 Days of My Search: 3 Searcher Case Studies

My Guests Today’s I speak with 3 searchers, each of whom are at different stages of their respective search journeys. As I have done in the past, I will again be asking these guests only a single question. That is: “Knowing what you know now, if you could go back and re-do the first 90Continue reading “What I’d Change if I Could Re-Do the First 90 Days of My Search: 3 Searcher Case Studies”

When Search Funds Don’t Go As Planned (Part 2): Trends & Observations With Jim Sharpe

My Guest My guest today is Jim Sharpe, somebody who I’ve been fortunate enough to call a mentor and friend for over 10 years now. This is Jim’s second appearance on In The Trenches (you can access the first episode here) In this week’s episode, we build upon the first-hand accounts presented in episode 1Continue reading “When Search Funds Don’t Go As Planned (Part 2): Trends & Observations With Jim Sharpe”

The 2023 SaaS CEO Survey

Listen to this Blog Post The Data Set The year in which each target company was acquired is detailed in the chart to the right. As can be seen, we were able to achieve reasonably good diversity by vintage year, with 18 of the 41 transactions taking place in 2019 or earlier, and 23 ofContinue reading “The 2023 SaaS CEO Survey”

Are You Selling to the Wrong Customers?

Listen to this Blog Post In my experience, among the countless strategic decisions that software CEOs must make, the decision of which end markets to serve doesn’t seem to command the time, attention, and level of thoughtfulness that it probably should. Leaders who run mature and established companies often take comfort in the product/market fitContinue reading “Are You Selling to the Wrong Customers?”

Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge

My Guests My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a cloud-based auto repair shop platform that counts Bain Capital Ventures among its investors. Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D’Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plumbing, and ElectricalContinue reading “Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge”