Culture

August 31, 2022
5 Takeaways from this Year’s Pulse Conference premium
Just before Pulse, I shared my (slightly biased) opinion on why Pulse is the Best SaaS Event of the Year. And our time together at the Moscone Center proved that again ten times over. We laughed together. We suffered through far too many of my dad jokes and Taylor Swift references. We celebrated all the […]
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August 26, 2022
How SaaS “Growth At All Costs” Costs Us All premium
This article was originally published on Fast Company. My morning mental health best practices includes things to not check: My phone. My email. My stock portfolio. If you’ve accidentally done the latter lately, you know things are very different than they were a few months ago for SaaS stocks. While the next few quarters are […]
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August 24, 2022
The Five Phases of SaaS Product Management premium
This article was originally published on Fast Company. My first real job was as a Product Manager at a software company in 2002. I remember sitting in my tiny, windowless office and launching my Windows XP laptop for the first time. And I remember asking the PM in the office next door to help me […]
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June 25, 2022
3 Takeaways from Surveying SaaS Investors About the Downturn premium
Anyone who knows me knows that I’m an annoyingly-positive optimist. But like every CEO, I’m also constantly paranoid. So two narratives are constantly battling away in my brain right now: “The market opportunity for SaaS has never been better.” “The stock market is down by how much?” After reading the 732nd memo from a VC […]
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April 30, 2022
I’m Biased But… Ten Special Things About Working at Gainsight premium
Every company claims, “you’ll never work somewhere like here” and, “we have the best company Values.” And I’m sure they are all (mostly) true. But there’s something really special about working at Gainsight – although I may be a little bit biased. I love talking to people. If you casually Google my name, you’ll find […]
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January 13, 2022
Gainsight Acquires inSided: The Past, Present, and Future of Customer Success Is Community premium
TL; DR (Too Long; Didn’t Read): Gainsight acquired SaaS Community Software leader inSided! For the mundane version of this news, click here. And to see a video of Robin van Lieshout (CEO of inSided) and me sharing the news, with a bit of rapping embedded. What comes to mind when you think of community? Maybe […]
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December 23, 2021
It’s A Wonderful Life (Despite What Twitter Tells You) premium
[Caveat emptor: I write this to share gratitude, but I also recognize that I am very fortunate in so many ways; many people are struggling.] Like many people, I am a creature of routine and habit. I have the same lunch every day (plain oatmeal with blueberries). I try to go to bed by 10 […]
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April 29, 2021
What If There Were No CSMs? premium
Imagine gathering Customer Success executives together and having them open up about pain points, processes, and the future of CS. Recently, I did, and inevitably, one topic and the incessant accompanying question arose, which is: How do we measure the ROI of our Customer Success team? In a happy hour earlier this month, we dove […]
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December 9, 2020
8 Things I Learned from Our Vista Announcement premium
Last week was a pretty good week. Scratch that, it was the best of my career. We announced a partnership with Vista Equity Partners, valuing Gainsight at $1.1 billion. As a result of that, pretty much everyone we’ve ever met at Gainsight reached out via email, text, LinkedIn, Twitter, Facebook, and probably Tik Tok (I’m […]
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October 16, 2020
Backstreet Boys, Zork, and Product Strategy premium
You are standing in an open field west of a white house with a boarded front door. There is a small mailbox here. And just like that, the keynote (err, I mean, game) is afoot! Two sentences and a blinking cursor was all it took to capture my imagination back when I first started leveling […]
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September 17, 2020
I Took 1 Million Steps to Stay Positive Through Zoom Quarantine premium
Emmanuelle Skala is the SVP of Customer Success at Toast, and I respect the heck out of her. She recently posted about managing “Zoom fatigue,” which prompted me to share what I’ve done to cope with 2020. I’ll say upfront that I am super privileged. I have a job that allows me to work remotely […]
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August 24, 2020
The End of Pre-sales (and Post-sales Too) premium
Martin Casado, former entrepreneur and current General Partner at Venture Capital firm Andreessen Horowitz, posted a thoughtful tweetstorm a few weeks ago. Through the series of tweets, he argued that as cloud and SaaS technology business models become mainstream, the notions of “pre-sales” and “post-sales” have become antiquated: “However, with the shift to bottom-up, this […]
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