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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

  1. 5:30 AM. Arrive, check-in, drinks, introductions
  2. 6:00 PM. Order food
  3. 8:00 (ish) PM. Wrap up
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Your Host
TopLeft

Most MSPs waste 15-25% of their capacity on work they can't see. TopLeft puts every ticket and project on one live board, synced to your PSA, so you deliver faster and grow without hiring.

Wim Kerkhoff
Wim Kerkhoff
Founder/CEO
wim@topleft.team