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A few weeks ago, we were fortunate to welcome Nick Mehta, CEO of Gainsight to SaaS Office Hours. I learned a lot from the session about how customer success has evolved over the last 5 to 10 years. Here are my notes from the session.

The discipline of customer success varies widely depending on price point. At the lower price points, some organizations combine the role of an account manager and the customer success person into a CSAM (customer success account manager). These CSAMs perform high-volume account management and customer success typically through email and other forms of broad campaigns to drive retention and upsell.

Next week, on November 14, Redpoint will host Office Hours with Anthony Kennada to talk about category creation. In the SaaS world, many businesses talk about creating new categories. To achieve this is rare, and it’s incredibly challenging to do. Anthony was a key part of the team at Gainsight that created the category that has just published a book on the topic called Category Creation, that we will talk about.

A few weeks ago, I installed Windows on my Mac using BootCamp. BootCamp allows you to have both operating systems on your computer at the same time and choose the one you want to use when. I was curious about Windows. So I installed it and tried to use it for a few days. Here are my impressions. Just as background, I’ve been on a Mac since I was seven and I last worked on a Windows machine in 2004.

There’s no doubt we’re in the founder-CEO era of startups. Ten or twenty years ago, hiring a professional CEO to run a business was de rigeur. But today, it’s less and less common. At the seed stage, nearly all CEOs are founders. No surprise there since the company is so young.

But at the Series D, founder CEOs helm approximately 70% of venture backed startups in the Bay Area. This is up from 53% in 2014. This share has increased by a third in five years. In fact, across Series A, B, C, and D, founders persist as CEOs more frequently.

In January, we welcomed Travis Bryant to join Redpoint as an Executive-in-Residence. Nine months later, we are welcoming him again as our first Partner of Founder Experience. Travis has always been one to think about ways to change the game. He excelled during his time at Salesforce and helped Optimizely grow to great heights from very early days as the first executive hire. Throughout his many successes, he’s always looking to innovate.

Today is the anniversary of Spotify IPO, which was the first direct listing of a technology company. It was championed by Barry McCarthy, the former CFO of Netflix and the current CFO of Spotify. Since then, Slack has also listed directly. And the combination of these two events has created a groundswell for more of them.

In the past few months and quarters, I’ve been learning as much as I can about this topic. Here are my notes and sources.

Dr. Daniel Kahneman features on the latest Farnam Street podcast and it’s a surprising episode. Kahneman wrote Thinking Fast and Slow. I admire Kahneman a great deal. Not for his Nobel or for his work, which are both impressive, but for his humility.

Some of the key tenets of Kahneman’s work in his famous book were disproved. And he owned up to it, both in print and on the podcast. That’s the hallmark of someone with great integrity, and it’s a sign to trust someone more.

We are very excited about open source software. Open source is a powerful distribution mechanism to get software and people’s hands early and easily. In an era where SaaS customer acquisition cost increases monotonically, open source can be a powerful antidote.

The other area that we are spending time in is open source at the application tier. Mattermost is our latest investment there, and we continue to look for others. They tend to be very capital efficient, fast growing businesses that can be quite disruptive.

We’ve all seen the data on the average increases in round sizes over the last four or five years. Startups are able to raise larger early rounds because of the financial environment.

One way of thinking about the early-stage fundraising market is as a collection of financial products. In 2008, there was a $5M series A product and a $10M series B product. Those were the most popular. As I’ve written about before, there’s now a continuum of financial products available to startups at the early stage.

In a recent interview, Sid Sijbrandij, the founder of Gitlab observed something about remote teams that I think is absolutely true. I’ve seen it in many of the remote/distributed companies we work with. He said:

Remote forces you to do the things you should be doing any way earlier and better

As companies scale, they need to develop infrastructure to successfully manage and coordinate large numbers of people. But in the early days, by virtue of being close to each other physically, it’s easier to delay some of these investments.