June 8, 2023
If you know anything about me or my leadership style, one thing is for certain: my strategies for being a CEO and a dad have some overlap. For both, I have the same five Taylor Swift puns ready to go on repeat (It’s me, hi, I’m the problem, it’s me), I will always try to capture Brené Brown’s empowering vulnerability, and I will always look to my family for inspiration.
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April 6, 2023
“I never make the same mistake twice. I make it 5 or 6 times, just to be sure.” – Random quote I found on the Internet If that doesn’t describe the CEO experience, I don’t know what does. In February 2023, I hit my 10 year anniversary (or “Gainaversary,” as we say) of running Gainsight. […]
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February 8, 2023
We’re officially two months into the new year, which means it’s time for a common annual tradition in tech: Reorgs. Though to be fair, reorgs seem constant these days. Yet amidst the usual shuffling and strategic planning for the new year, I’ve seen a new trend emerge: companies are combining their Customer Success Management (value/adoption) […]
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January 28, 2023
The Chief Customer Officer (CCO) role is crucial for virtually every SaaS company. Hiring one moves Customer Success (CS) from a function to a company-wide strategy, offering a customer voice in the boardroom and a peer to your Sales and Product leaders. Yet if you asked 100 SaaS CEOs to define a CCO’s roles and […]
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January 18, 2023
Given the uncertainty in the world right now, it’s hard to predict what will happen this January—let alone all of 2023. Besides the Taylor Swift Eras concert being epic, of course! So, I decided to get the scoop. A couple of weeks ago, I sent out a survey to hundreds of growth-stage SaaS CEOs to […]
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December 16, 2022
I get an email almost every day from other CEOs or CXOs that goes something like this: “What’s a good metric for… [Growth Rate / Net Revenue Retention / Gross Margin / ARR / Employee]?” Often the message provides no context on the leader’s business. They just want to know what “good” is. As a […]
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December 16, 2022
How will we look back on 2021 and 2022 years from now? I’m sure partly, we will reflect with shock. How did we ever think GameStop was worth tens of billions of dollars? Why did we believe in crypto scams like FTX? And whoever thought an NFT of a “Bored Ape” would be valued at […]
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October 20, 2022
This article was originally published on All Business. I’ve always longed for an archnemesis. I know that may sound strange, but I’ve seen enough superhero movies to know that every great hero needs an antihero. We all know that Superman isn’t anything without Lex Luthor, and that Batman can’t quit the Joker. via GIPHY Somehow, […]
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September 22, 2022
One of my favorite TV shows ever is the 2000s comedy Community. The show features six-ish community college students who become unlikely friends. I love the program for many reasons. First of all, it’s one of the most meta TV series ever, in that it’s mainly self-referential about TV tropes. And if you know me, […]
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