HEY, I'M JESSE.

THIS IS WHERE I POST MY BEST THOUGHTS.

Onwards and upwards–An overly procrastinated update

Last week, I decided to relaunch my personal blog. I’ve been doing a lot of writing lately, however, none of it has been published to this site (I hope to cross-post that content here over the next few weeks.) Maintaining a consitant writing cadence is something that I’ve always enjoyed, and something that is easy to find time for when I’m at my best. That being said, sometimes life just gets busy and when your Jekyll site breaks because you installed the wrong version of a Ruby Gem, finding the time to troubleshoot it and get it back up and running is hard.

All that to say, I’m long over due for an update here, not to mention a face lift for this site, which I hope you like :)

I climbed the ladder and I cannonballed off

The past few years have been full of ups and downs, a sign that I’m still alive?

I weathered the chaios of the pandemic and tech’s great resignation at AWS, which was an absolute joy. AWS is a machine, it exposed me to some of the smartest people I’ve ever worked with, pushed me to raise the bar with my own deffinition of excellence, and gave me the opportunitiy to contribute to and lead a few really big projects. Some of the highlights include working on repositioning AWS in the DevOps category alongside Emily Freeman and now MongoDB CMO, Peder Ulander, leading the messaging for GitOps and IaC at AWS, and bringing Kubernetes and containers into the Serverless EDA messaging and positioning, which ended up being a focal point for Werner Vogel’s 2022 reInvent keynote.

Success at a company like AWS opens a lot of doors, for me that was a VP role at Docker. Docker is one of the most loved and used developer tools. When I was getting started in tech it seemed like every week there was a Tech Crunch article covering their innovation, partnerships, heck even their jungle like offices in SF. Unfortunately that version of Docker (focused on Docker Enterprise) didn’t pan out and a small team rebuilt the company around Docker Desktop.

There are a lot of questions around the company, how they participated in open source, how they price, etc. But what you can’t question is the value they bring to developers. When I joined Docker they had secured a $102M investment at a $2.1B valuation. They were a little over $50M in ARR on a crazy trajectory to $100M, and by the time I left had surpassed that number by quite a bit.

I saw the role at Docker as a opportunity to roll my sleves up at a company that had everythign going for it, or so I thought. The thing about companies is that they are a lot like people, you have to do life with them to really know who they are and what they are about. It didn’t take long to discover we weren’t a match and thought I had built a killer team that was just hitting their stride, we decided to part ways.

When one door closes ... you know the rest

My roots are in the startup space. When I think back on my most enjoyable work memories they are with early stage companies. Companies where I was playing a pivotal role on a small and dedicated team who was determined to change one little part of the world. It’s not for everyone, but something about risking it all for the chance of a big win puts a smile on my face and some pep in my step.

Before leaving Docker I had begun playing with the idea of templatizing my method for creating product messaging and positioning. Leaving Docker gave me the time I needed to put pen to paper and what resulted was what I call the Stori Messaging and Positioning Framework. I worked with my now co-founder to pitch it to a few companies and what do you know, people wanted to buy it. Even more exciting was that it led to some really great results in a very short amount of time. This led to the birth of https://gostori.com which now works with PE and VC firms to help their portcos communicate value and differentiate from the competition. We take on a limited number of projects and work with founding teams who are highly invested in developing messaging (and who we actually like.)

The cherry on top for this season was a serindipitous co-founding of a software startup called Jozu, which is built on open source KitOps.

It all started the CEO of Jozu (someone who I’ve spent most of my career working with and for) reached out to see if I wanted to help lead marketing and operations for his incubation funded project. At the time the project (maybe more of an idea in progress) was a marketing analytics tool for APIs and machine to machine interactions. Having spent some time in the very crowded and competitive GTM software space I knew exactly what I was getting myself into and was a bit concerned.

Eventually my concerns were brought up by other members of the team and we ultimately decided to pivot. This led to the creation of KitOps our open source MLOps tool. We built KitOps to solve a problem that we were feeling internally at Jozu, which was how to handoff models from a data scientist to a software development team and then to a DevOps/SRE team, more on that here. Then turn Jozu into a Hub for KitOps ModelKits, our OCI-compliant package for AI/ML projects.

Long story short, I’m now the co-founder of two companies, one in the services space and one in the software space. I spend a lot of time on the software side of things which is very much a passion project for me. When I’m not doing that I enjoy working with other founders to uncover the value of their products, communicate their product vision, and build a more differentiated message for their GTM efforts.

Is it a lot, sure. But I’ve always been someone who’s had a side project, heck for most of my career I’ve flipped houses in my spare time. Ultimately, when you work on things you love with peolpe you guenuinly like and care about the day just seems to fly past.