Get Good at Delivering Software™️

The 2026 CircleCI State of Software Delivery report confirmed what many of us had suspected: AI-driven code generation is real and measurable, but most teams are not converting it into shipped software.

The CTO must own the entire software development lifecycle (SDLC) from cradle to grave.

Every decade or so the software industry undergoes a major shift in the way software is built and delivered.

Private equity may like high margins in a portfolio company, but what they really like is growth.

When I was an architect in Infrastructure Engineering at Salesforce, they would periodically hold all-hands meetings where everyone in San Francisco would go to the Masonic Auditorium so we could all be in the same room together.

It was a wild year.

I recently stumbled across a podcast I was a guest on years ago that had gotten lost in the shuffle.

It’s almost impossible to open LinkedIn, social media, or your kid’s PTA newsletter without reading about how AI will change the world.

The company has been doing well.

I’m brought in to work alongside portco CTOs because I’ve seen a lot of things before and I “know what good looks like”.

Part of letting go of the old ways of doing things requires being a little bit uncomfortable.

In the late 90s, I had a roommate who worked in the corporate IT department at Williams-Sonoma, the kitchen goods company.

I see it often.

If a tree falls in the forest and there is no one there to hear it, does it make a sound?

Generative AI is by far the hottest topic in the industry right now.

Different companies experience increased traffic at different times of year.

There’s a phrase I hear from executives when working with portfolio companies that I’ve never liked: Do more with less.

Automation, automation, automation.

I saw a few interesting bands a few months ago at The Kilowatt in San Francisco.

Most digital transformations fail (87.5% fail to “meet their original objectives”).

Internal DevOpsDays, Engineering Conference, Tech Summit.

In W.

When working with portfolio companies, the question of how and when to do testing comes up often.

The team spent 18 months replacing the database where all user data was stored.

“Dave, we can’t release more often, our customers wouldn’t tolerate it.”

We’ve all seen the professional juggler at the carnival who asks to be thrown more balls.

Heard in the course of doing the interviews at the start of an engagement: The ops folks just make up things to do, they don’t want to help the developers - a senior developer (my personal favorite) My product is the most important product for the business

It’s the beginning of the year and perhaps because many fear a recession and there is a concern about operational efficiency, there seems to be a lot of discussion lately about technical debt.

Hofstadter’s Law: It always takes longer than you expect, even when you take into account Hofstadter’s Law CTOs want less risk of something going off the rails and more predictability as to when something will be delivered.

Shift left!

With recent bear market dips, it’s a good time to shut down marginal products rather than maintain those which generate little revenue/are not the future of the company.

“The cloud” is something that is talked about often.

The company is growing or has grown.

Engineers dislike meetings.

Many people have heard of the SaaS Rule of 40.

“Dave, I was talking to one of our portfolio CEOs and she has major concerns about her cloud engineering team.”

“This would be so much easier if we could just use VMWare Motion.”

I began my career as a developer.

I was getting coffee in lower Manhattan with a friend who works in private equity.

While watching the 2.5 Hour Symposium by IT Revolution, a number of things jumped out at me.

I’ve watched a lot of trends happen in the industry over the years.

This post was originally published on CIO.com on June 7th, 2021.

Them: “Dave, what should we do here?”

This post was originally published on TABBForum on March 24th, 2021.

This post was originally published on CIO.com on March 17th, 2021.

Game Changer Over the years, a number of high performing software organizations have figured out many of the keys to delivering software with both speed and quality, what is now collectively known as DevOps.

The company has decided that the benefits of public cloud are too great to ignore any longer.

“How do you scale an organization?”

There are engineering concepts that are difficult to quantify.

Last last year, I stumbled upon the Growth Gurus series of 30 interviews with different leaders in the Insight Partners portfolio.