Operators Guild

Poker Night during Chicago Tech Week was one for the books — packed house, great cocktails, and even better company. Huge thanks to our partners Ghost Social and Poker Power for bringing the fun, and to our sponsors Justworks and Spendflo, and Ghost's sponsor Merrill Lynch, for making it all possible. Whether you came to play or just came to hang, we’re so glad you joined us at the Untitled Supper Club for an unforgettable night with the OG crew and the Chicago tech community. ♥️

OG #SF members set sail, taking in the views, sharing stories, and catching up with some of the best operators in the Bay. Good people, great conversations, and a little sun on the water. Huge thanks to our sponsors, Heffernan Insurance Brokers, Paylocity,  and Unum, for helping bring the OG community together for a truly special afternoon. Thanks to everyone who joined — Meredith Parsons, Olya Krasnykh, Jon Michaels, Nicky Khaki, Michelle Ma, Sandip P., Daniel de Mos, CPA, MBA, CMA, Mingming Wu, Serge Gusev, Trish Emhof, Randy C., Lyonna L., Anshul Shah, Sri Naraharasetti, Kenna Ranson, Cinthia L., Brandt L., Stephanie Tan, Katrin Robb, Aarti Bhatnagar, CPCC, ACC, Molly Gunderson, and Sun Choi.

What a special evening with an exceptional group of operators. Huge thank you to Paige Fitzgerald, COO at Patreon, and moderator Seth Greenberg for an incredibly thoughtful OG fireside chat! Paige walked us through a career shaped by curiosity and experimentation —from public service to tech and now leading operations at Patreon. She opened up about what it means to build teams that actually thrive, and how she’s thinking about AI in both her work and her leadership. Some highlights: 👉 A refreshingly honest take on management 👉 The power of knowing your operator superpower — and how to use it 👉 Lessons from building across org structures, hardware/software timelines, and company cultures 👉 Her approach to leading with mission A huge thank you to our sponsors Brex, Justworks, and Spendflo for making this evening possible, and to the amazing OG members who joined us. Thanks again to Paige and Seth for keeping the conversation real, honest, and genuinely useful. Here’s to more honest conversations, shared lessons, and the kind of leadership that lasts. 🥂

What a night with OG #Seattle members! We met up at Nick's on Madison and covered everything from AI “slop” in marketing to unpaid invoices. We swapped Seattle Tech Week recs, talked about layoffs and messaging, recapped the OG Summit, and shared how we’re actually using AI in our own orgs. Huge thanks to chapter leads Hannah Weisman, PhD and Darcy Rubel for bringing everyone together. Appreciate everyone who came out and made it such a thoughtful, honest conversation: Erin Trimble, Atul Sahai, Scott Nagel, Yashbir Narechania, Erik Winters, Garritt Chrzanowski, Giang H., Juliana Su, Janice K., An N., Sean Skyllingstad, and Soon-Chul Choi CPA. Already looking forward to the next one!

The OG #LA community came together for a night in the Arts District, this time at Alloy, a stunning creative space brought to life by SIP LA. With a one-night-only menu crafted by Chef Jasper Lynn (Netflix-featured, House of Suntory’s 2023 Rising Chef of the Year), the evening brought together sharp operators, bold flavors, and real conversation. Topics ranged from navigating $100M+ fundraises to building the operational foundation for early-stage companies — the kind of tactical, honest discussion that defines this community. 👏 Huge thank you to sponsor Todd Northrup & Jonathan LaMantia and Armanino for making the night possible. Special thanks to chapter lead Hogan L. for organizing, and to everyone who joined us around the table: Echo Zhong, CPA, Mark Dhillon, Peter M., Estelle Cramer, Bernier Lauredan Jr., Felix Pomerantz, Lawson Dees, Jack Cheap, Joe Caiello, Aaron Altamura, Mike Filliben, MBA, Mianya O., Robert Johns, Jonathan Zhang, David Kramer, Chris Da Silva, CPA, and Anitha Jathindira, CPA. Can't wait for the next one! 🥂

Great insights from last week’s AI-focused OG #Raleigh lunch and learn event with expert Robbie Allen (builder of 3 AI companies) and presentation by Joe Aurilia, Jr., SVP at Cyware. Thank you to Lucy (Hansen) Meade & Kate Wilburn LaSacco and J.P. Morgan, for collaborating on this event! Three key takeaways that stood out: 👉 Use case first. While AI can be a broad tool, it’s most effective to be specific. Map your workflows, identify specific pain points, then apply AI where it genuinely improves quality or speed. 👉 The discipline challenge. Like going to the gym, knowing AI is beneficial isn't enough — we need to build sustainable routines and processes around it. 👉 Security solutions exist. Data concerns are valid but manageable through open-source models like Llama, limiting data access by use case, and other security frameworks. Can't wait for more like this!

The Operators Guild #NY Chapter ordered up some perfect weather for its annual BBQ & Pool Party this weekend, hosted at the upstate house of our Chapter Lead, Robert Owen. 😎 With a few spouses joining us for some family fun, we had a relaxing time escaping the heat in the pool, playing corn-hole, and feasting on a culinary world tour of BBQ. Thanks to Abigail Keene-Babcock, Faraz Siddiqui, Gilad Rotem, Lauren Sydney Smith, JD, Mitesh Popat, Scott Bieker, Victoria Bian, Thomas Meyer, and Allison Paley for coming!

OG members gathered at Cotogna last week for an early-stage Finance dinner hosted by Dean Quiambao, Partner Quiambao and the Armanino team. What started with updates on private capital markets and M&A turned into a wide-ranging conversation about AI tools in the wild—and eventually, an unexpectedly passionate debate on the economics of dog ownership (nearly 75% of the group had dogs, mostly Doodles). Thank you, Jon Michaels, for leading and a huge thanks to Dean and Armanino for sponsoring. And thank you to everyone who attended — William (BJ) Ebert, Christian V. Bergmann, Shuchi Bhargava, Chris Truglia, Patrick Mullin, Trish Emhof, Chris Seidensticker, Liam Corrigan, Erin Springmeyer, Stephanie Tan, and Paul Dreyer. See you next time!

Some of the OG #Miami members met up at Lagniappe for a happy hour to kick off summer. Good people, good conversation, and an overall great time! Thanks to everyone who joined —Ty Boshyan, Esteban Ochoa, Hari Raghavan, Chris Tischner, CFA, and Joao Barbara & Pedro Cabassa for leading the charge. We’re just getting started in Miami. 🌴 Can't wait for the next one!

The OG #LA members met up for dinner at Cosetta, which brought together some of the sharpest operators in the city for an evening of real conversation, new connections, and shared insight. A huge thank you to Estelle Cramer for leading the night, and to Aron Schwartz & Michael Carpenter and Intercom for making the evening possible. Thanks to everyone who came out — Aaron Altamura, Alex Rosten, Anna vo, Benjamin Lantos, Bernier Lauredan Jr., David Kramer, Dominic R., Gregg C., Jack Cheap, Kathleen C., Mark Dhillon, Mark Kim, Mark Romagnoli, Matthew Prosser, CFA, Michael Lee, Michael Riordan, Sean Twersky, Tina Ong, and Van Cong. The room was full of operators comparing notes, asking questions, and connecting in the ways that make this community what it is. More of this, always.