Stay SaaSy

Book the Meeting Before You Need It As companies get larger, scheduling a decision starts to take longer than making it.

Imagine that you’re in a board room, locked in an intense negotiation.

Everyone knows that lying to your team is bad.

In the course of conversations with startups that I’ve invested in, that I advise, or that I simply encounter, it’s very common to get into discussions about prioritization.

A lot of people simply don’t understand the degree to which competition matters in B2B software, and what competing effectively feels like.

Technology businesses are heavily influenced by waves of technology change, like the rise of the internet or AI.

Building a great organization is all about finding skills that complement each other.

What It’s Like to IPO When baby sea turtles are born on the shore, they immediately rush by the thousand towards the ocean.

True startup people are one of the most important advantages that many tech companies have.

AI tools hit a true inflection point in late 2025.

There is enormous variability in the frequency with which teams have emergencies.

The most important teams in a B2B software company are engineering and sales.

It Was A Very Weird Year It was an interesting year in the Stay SaaSy universe.

This is a guide on how individual contributors (ICs) can achieve outsized impact within a software organization.

Compensation is difficult.

Own a Graph If you are a senior engineer or PM or designer, you should own a graph.

One of the hardest things I’ve found about being a Head of Product / Chief Product Officer is that you really have two jobs: The first is setting up a strong product culture, establishing strong design/roadmapping practices, mapping out product processes,…

The best way to win as a business is to move fast.

As companies grow, there is a stark shift from having a team of generalists to a team of specialists.

The traditional advice for tech companies is that you should ignore your competitors.

One of the biggest mistakes is shielding people from the pain they need to learn.

One of the most consistent observations I’ve had in my time in startups, scale-ups, and public companies is that smart people with context on a tricky situation almost always know exactly what they need to do.

Metrics can be incredibly powerful.

Forming a new software team is easy to get wrong in many ways, including: Making a B team Making a low context team Here, however, we’ll focus on one of the most important and often bungled aspects of team formation - the team name.

A common logical fallacy is claiming something won’t work because a previous attempt failed.