Chicago MSP Dinner Meetup: CEOs, Project & Service Managers, August 2026

A small-format peer dinner for IT/MSP CEOs, project managers, service managers, and operations leaders.

What gets covered depends on who is in the room, but the themes tend to land on the similar interest topics: AI (of course), PSAs, RMMs, hiring, training, marketing, dispatch, automation, project management, security, vendors, conferences.....

Great conversations with great people. No vendor pitches/presentations!

What to expect

5:30 AM. Arrive, check-in, drinks, introductions
6:00 PM. Order food
8:00 (ish) PM. Wrap up

❯ Previous Meetups

❯ What Guests Say

“It was refreshing to meet other MSPs and speak openly about our respective businesses rather than being concerned about competition. We had some great collaborative discussions, planting seeds for future get-togethers.”

Kris HarnessPresident, KDH Consulting

“I enjoyed getting to talk with you and the other hosts and connecting with other MSP leaders. Hopefully you'll continue putting these events together!”

Paul ZimmermanCTO & VP, Fidelis

“Yes, let's do this again! It was great getting together with other local MSP leaders and having open, genuine conversations on a variety of topics. Looking forward to the next one!”

James AmmonsCTO, KDH Consulting

“It was great to meet you and the other vendors as well as the other MSPs!”

Gary KawamuraBusiness Development Manager, Dynamic Computing

“It was great to just have a normal conversation with peers. Some time to talk shop but also just some time to enjoy lunch. I would love to go back and meet more people at these events. Thanks again for having me.”

Alex Boyd

❯ Your Host

TopLeft

Most MSPs lose 15-25% of capacity to tickets and projects scattered across tools. TopLeft syncs it all to your PSA on one visual board, so you can scale without adding headcount.

Wim Kerkhoff

Founder/CEO

wim@topleft.team

❯ Brought To You By

Acronis

Acronis gives MSPs one platform for backup, disaster recovery, cybersecurity, and endpoint management, so you can protect clients and grow services without juggling separate tools.

Steffen Bredahl

Strategic Channel Account Executive

steffen.bredahl@acronis.com

Bailey Yntema

Senior Distribution Account Manager

bailey.yntema@acronis.com

Alternative Payments

We provide MSPs with an all-in-one payment integration that supports a variety of local payment methods, enabling them to streamline transactions and reach new markets.

Jackson Miller

jackson@alternativepayments.io

ThreatLocker

Stop attacks before they happen. ThreatLocker brings a Zero Trust framework to your organization with controls that put you in charge of what runs inside your environment.

Garrett Anderson

Sales Development Representative

garrett.anderson@threatlocker.com