Ole Gjerde, smiling, in a blue t-shirt

Yes, I own other shirts.Probably

Hi, I’m Ole

I was very comfortable being number two.

For most of my career I was the COO, the operator, the person who made the plan actually work. When we split the Dynamics business from the MSP in 2021, somebody had to be CEO. Katie (my wife, now our CFO) and Scott (our COO at the time) decided it was me, and they were persistent about it.

So here we are. I run TruNova, a Microsoft Dynamics 365, Power Platform and Copilot partner, and I write here about what I’m learning in the chair I never applied for.

It’s been 27 years of software, web design, IT, managed services, consulting and Dynamics, from small businesses to midmarket and now enterprise. There have been a lot of mistakes and a lot of learning, and now I’m figuring out how to lead, how to change a company’s culture, and how to become a new kind of company without leaving long-time people behind.

I grew up in Ålesund, Norway, and traded the fjords for North Dakota, which is about as flat as a place can get. Colorado finally gave me mountains again, though I still miss the ocean.

The short version, 1999 to now

The CEOle squirrel shrugging, palms up
  1. 1999

    Started Ignus Technologies with Wes Henry

    October 1999. Two techy nerds who said “why not start a business, it can’t be that hard.” Turns out it’s pretty damn hard. (I also squeezed in a stint back home in Norway along the way.)

  2. 2010

    Merged with Insight Technologies

    Turns out that was a big mistake… with big lessons.

  3. 2011

    Co-founded ConnectBooster

    Wes and I wrote the code for this ConnectWise payment add-on for MSPs, then I stepped away to focus on TrueIT. It later sold for a lot of millions.

    I’m not bitter. My wife is.

  4. 2012

    Started TrueIT

    The MSP years, in full swing.

  5. 2018

    Acquired Summit Group Software

    How I got into Dynamics. We thought combining two very different business models was a brilliant idea.

  6. 2021

    Split the businesses. Became CEO.

    In April we split the Dynamics practice out of TrueIT, and TruNorth Dynamics officially opened its doors on January 1, 2022.

    Katie and Scott made me do this. Blame them.

  7. 2023

    Sold TrueIT

    Technically a sale. We didn’t get much, but the MSP chapter was officially closed.

  8. 2025

    Bought out two partners

    And just like that, it’s back to Wes and me. Twenty-six years later.

  9. 2026

    TruNorth became TruNova

    New name, way better logo, and a bigger vision for the future.

Ask me about

Leadership, Microsoft, and AI

Especially the parts that didn’t go to plan.

Squirrel brain

ADHD, the squirrel kind

Massive ADHD. The mascot is a true story, too: a real squirrel kept stealing my attention through the window during Teams calls. I also found out at 49 that “always slightly worried” is called anxiety. Who knew.

After hours

I still build things

Claude, Codex, Cursor and Grok are my late-night crew. I built our cash flow forecasting app myself, plus a pile of other stuff, because I can’t help it.

Outside work

Will travel for food

Spicy food, Japanese, BBQ… I just love food, and most of my travel is an excuse to eat somewhere new. I also sold the house and rent now, and I don’t miss a single HOA meeting #Freedom.

Fair warning

Dad joke of the visit

I’d make a Dynamics joke, but it would need a three-month implementation.