Connecting, Collaborating, and Building the Future: Highlights from the StitchStudio Chicago Offsite
This September, we brought StitchStudio's core team together with the advisors, customers, and investors who have helped shape this company from its earliest days.
Connecting, Collaborating, and Building the Future: Highlights from the StitchStudio Chicago Offsite
This September, we brought StitchStudio's core team together with the advisors, customers, and investors who have helped shape this company from its earliest days. We gathered for two days of connection and collaboration in Chicago.
"I didn't realize this until this morning, but this feels like a gathering of my favorite people over my career," Karan, CEO of StitchStudio, told the room as things got underway.
Day One: Ravinia
We opened at Ravinia, a local nonprofit that's given Chicago live music for more than a century.
We took in a live performance from the Chicago Symphony Orchestra, worked our way through some great hors d'oeuvres, and spent hours connecting in person.
Day Two: The Work
We looked honestly at our own journey so far — what's working, what we've learned, and how our thinking has evolved as the company has grown.
"We came from the industry," said Ammon Dixon, our Head of Product Delivery. "We've been in these spaces, we've built the relationships, we understand the compliance."
We heard directly from our advisors and investors, whose outside perspective is one of the most valuable things we get from a room like this.
From there, we went deep on what we're building. The architecture behind every agent, and the roadmap ahead.
We showed our impact through real, quantified outcomes with customers that are live today and how we tell that story: at conferences, in the press, and in front of an industry that's watching.
And we looked ahead by pressure testing our roadmap with our industry advisors in a powerful strategy session.
Our advisors and investors gave their honest feedback and pushed back where they disagreed, which is exactly why they were in the room.
"When you build it this way, that's what really matters," said Nick Rockwell, who leads go-to-market for Employee Benefits, "because it's your business partners saying: I want to work with this team because I trust them, because they understand me."
Why It Matters
An offsite is easy to treat as a break from the real work. We don't see it that way, the clearest thinking we do all year tends to happen when we step back and let the experts challenge us and expand our thinking.
We left Chicago with more clarity than we arrived with. The work in front of us is clear and the path forward feels sharper than it did a few days ago.
We'll see everyone at the next one.
