I’ve been in SaaS for over two decades. I’ve seen it all—from duct-taped onboarding flows that accidentally convert, to UI tweaks that
Abundance and Displacement
I’ve had some intense conversations lately—friends who run VC firms, founders building on the frontier of AI, and business owners seeing the
The Mirage Age
In the swiftly evolving landscape of artificial intelligence (AI), we find ourselves living in what I call “The Mirage Age.” This era
Toxic Assets
In 2008, the world witnessed a financial crisis of unprecedented scale, largely precipitated by the collapse of the housing market. A significant
The Great Reset
I was having lunch with a friend last week who leads HR at a Fortune 500 company. They just finished a large
Healthy in a Hybrid World
The Covid pandemic forced the majority of the global workforce to abandon their traditional office space. It challenged them to create a
Leading in Difficult Times
The last few years has been one of the most challenging events of our time. And while some of have pushed forward,
The Illusion of Output
We are in the midst of the one of the most fascinating shifts in modern labor. Businesses are desperately trying to get
Not Everyone Can Be a CEO
“My goal is to be the CEO one day.” I have heard this line a thousand times when I ask people what
Kevin Maye
100 days on the job. Most new employees are barely out of formalized onboarding in 90 days, let alone quitting their job.
Why I Quit LinkedIn
After 10 years of the hustle and grind, you can say I had “made it.” Fortune 500 companies. Mergers and acquisitions. Running
Slack is Afraid of Microsoft
Stewart, I’ve been your #1 fan since day one. An investor since your IPO. A power user since we adopted it Aha! and
Vulnerable Conversations at Work
The year 2020 will forever be remembered as a year of change in business. Both the medical and social levels demand a
Law School and Learning
There was a time when law school was my future. It was all I thought about day and night. From researching the
Big Auto vs. Tesla
9 years. It’s a long time in the real world. And an eternity in the tech world. That is how long of
Slack’s S-1 Filing
Slack released their S-1 today, and as usual with SaaS companies I took time to read through it. I do not usually