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Strety User Group Chicago 2025 Recap

Strety customers are seriously the greatest. They’re thoughtful people who are passionate about creating calmness and clarity at work for themselves and their teams. They are entrepreneurs, visionaries, integrators, and champions who help their teams row in the same direction, and whether they’re working to align 8 people or 800, they are tireless in their efforts to make work better.

Plus, as new and old customers know, you all have provided the feedback that’s helped Strety evolve into the product it is today, and the product it will be in the future. Even though we don’t believe in traditional product roadmaps, if we ever did, you could just picture your face on it.

TL;DR: we love our customers.

After hosting half-day, small user groups in Sydney and Melbourne adjacent to international EOS conferences, we launched our first full-day event in Chicago. We wanted to give our customers a super-valuable day, and from the feedback we’ve gotten so far: mission accomplished! 

Here are the highlights of our inaugural full-day user group meetup, and our plans for 2026.

Who was there?

After much back and forth, we decided to keep our first group small — only 25 people. We wanted to ensure we had the capacity to get maximum participation and interaction with each person. We put the call out to our current customers, expecting mostly midwestern folks to sign up since we were holding it in Chicago. To our surprise, people from all over the country signed up!

Our group represented 20 organizations, 8 industries, and the whole gamut of EOS implementation — from relatively new self-implementers to people who had been working with EOS implementers for years. They also ran the spectrum of time spent on Strety — a customer who only joined us three months ago to longtime users who’d seen the big evolution in the product over the past year.

We also were thrilled to have Beth Fahey, Expert EOS Implementer, author, podcast host, and all-around superstar join us. Beth shared an awesome presentation on Rollout (more on this below) as well as her wisdom throughout the day.

From the Strety team, we had cofounder Brian Dosal, our Head of Success Derek Weaver, customer success manager Maddision Klitgaard, and me, Head of Marketing and chief event organizer/worrywart 🙂

What did we do all day?

Our agenda was fantastic! Here’s the full rundown:

9am

Welcome + Strety Introduction | Brian Dosal, Strety CEO

CEO/cofounder/product guy Brian Dosal welcomes you to our User Group!

9:30am

Recent Release Overview | Derek Weaver

Learn about our favorite recent releases!

10:00am

Strety Deep Dive Training! Part I | Derek Weaver

Tips, tricks, & best practices to get more from Strety.

11am

Break

☕️

11:15am

Strety Deep Dive Training! Part II | Derek Weaver

Tips, tricks, & best practices to get more from Strety.

12pm

Lunch

🥗

1pm

EOS Rollout | Beth Fahey, EOS Implementer™

Dive deeper into EOS® with Expert EOS Implementer™ Beth Fahey. Learn more about Beth here: https://www.eosworldwide.com/beth-fahey

2pm

Rolling Out EOS Across Communities | Maddison Klitgaard

Before Maddison was on our team, she was a Strety power-user who rolled out EOS + Strety at 36 communities from her org’s home office. Hear her story and ask her questions!

2:30pm

Break

☕️

2:45pm

Group IDS Session | Beth Fahey, EOS Implementer™

Bring your thorniest Issues and let your peers, Beth, and the Strety team help you walk away with real resolutions.

4:30pm

Roadmap + Feature Request Voting | Brian Dosal

Help us walk away with one great feature to add to our next dev sprint — and hold us to getting it in the product quickly!

5pm

Happy Hour!

🥂

Agenda Highlights

The whole day was fantastic — lots of engagement from our awesome customers, and lots of ideas shared in the group. Here are some of the best parts of the day!

Strety Deep Dive with Derek Weaver

Our very own Derek Weaver took the lead on an awesome deep-dive session covering our favorite recent-ish features. It was fun to see people having aha moments in real time, and getting excited about deepening their Strety usage. And of course, color commentary from the guy building the product 🙂

We got a lot of feedback that “We didn’t know Strety did that!” which was cool to see, but a great eye-opener for us. We ship so much, so often, that it can be hard for our customers to keep up! Good problem to have, but still a problem we’re thinking about solving.

EOS Rollout with Beth Fahey

Our group had the pleasure and privilege of hearing Beth’s Rollout presentation for the first time. Her upcoming book on EOS Rollout will serve as a practical guide to teams looking to create beautiful harmony in their EOS implementation as they roll out beyond the leadership team. The presentation was awesome and we can’t wait for the book!

Plus, Beth generously lent her knowledge throughout the day — giving us her frank thoughts and deep expertise to our groups most pressing problems, and practical advice for how to get the most out of their EOS implementations. We can’t thank her enough. If you’d like to gain the benefit of Beth’s wisdom, her podcast, Bad Boss Confessional, is an awesome way to start. The cover art is perfect and the conversations about imperfect bosses are rich with insights.

Internal Implementation with Maddison Klitgaard

I personally ADORED Maddison’s presentation where she discussed rolling out EOS across dozens of senior living communities in her former role. It was such a fun follow-up to Beth’s Rollout presentation, from a deep operation perspective. 

After doing a case study with Maddison in July, she joined the Strety team in September, and now is helping people with their own Strety rollouts. From Strety customer success story to Strety customer success manager: talk about a full circle moment!

IDS/Feature Request Session

After Derek ran an awesome IDS session that covered the most burning questions, from how to engage people who are resisting EOS implementation, to nitty-gritty feature questions, Brian conducted an awesome feature request session. 

The product maestro helped surface the groups most pressing requests, and we came away with a great list that our devs are already running down. When you see improvements and extras in the product in the next couple weeks, you’ll have this amazing group of customers to thank!

Awesome way to cap off an awesome day!

What are our future plans for user groups?

In a word: more!

We’re planning on hosting four more user groups in 2026 — aiming for one a quarter in cities around the United States. Each user group will build on the success of the previous one, so we’re sure they will only continue to get better!

Hope to see you next time!!

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