Mind the Product Leadership Meetup Chicago: How to hire and structure product teams

Join us on the evening of Wednesday, October 29th in Chicago for a FREE, invite-only event designed specifically for product leaders - and trust us, this is one you won’t want to miss.

This time, we’re getting laser-focused on one of the most defining aspects of successful product leadership: how to hire and structure teams that can scale with confidence and deliver real impact.

Expect an evening of candid conversation, actionable insights, and a few hard truths about what it really takes to build a high-performing product organisation in today’s fast-moving landscape.

We’ll dig into questions like:

• How do you spot talent that will thrive in your unique context?
• What does a resilient, future-ready team structure actually look like?
• And how do you avoid the common trap of hiring for today, while tomorrow's challenges are just around the corner?

Whether you’re building from the ground up, scaling fast, or reshaping for what’s next, this event is your shortcut to sharper thinking and stronger teams.

Come for the insights. Stay for the unfiltered conversations and meaningful connections with fellow product leaders who’ve been there.

Roundtable Topics

• How to define and facilitate ‘high-performance’ in a product team context
• Creating an effective product org structure
• Mastering career development for your product team
• Building and upholding the right product culture
• Leading through uncertainty

Schedule

• 5:30pm - 6:00pm: Networking and refreshments
• 6:00pm - 6:10pm: Opening remarks
• 6:10pm - 7:10pm: Presentation and Q&A w/ David Jesse + Sean Flaherty
• 7:10pm - 8:05pm: Curated small group discussions
• 8:05pm - 8:30pm: Closing remarks, networking and refreshments

About the speakers

Sean Flaherty began building software products at age 11 on his Commodore Vic-20 and hasn’t stopped since. He studied aviation electronics in the Navy, molecular genetics at the University of Rochester, and earned an MBA from the Simon School of Business. Over the past two decades, he’s worked closely with clients to build innovative software that moves, touches, and inspires. As EVP of Innovation @ ITX, Sean leads a team of passionate technologists and artists who create impactful digital experiences every day. He teaches MBA candidates at the Simon School and speaks globally on innovation, culture, and empathy. He also developed “The Momentum Framework,” which maps the patterns and language of successful leadership. His work has earned accolades including Vistage’s 2019 “New Speaker of the Year” and Trust Across America’s “Top Thought Leader in Trust.”

David Jesse is a product advisor and leadership coach who has built and scaled product organizations from the ground up over 25 years. He's navigated and consulted on the full spectrum of team-building challenges—from hiring the first product manager to rapid growth phases to restructuring teams through downsizing.

As the first VP of PM and Design at Groupon, first Chief Product Officer at Fetch, and leader who established DoorDash's International Product team, David has experienced firsthand what it takes to create high-performing teams that thrive through uncertainty and change.

He currently leads Crescendo Product Group, where he helps product teams transform their product practices and product leaders accelerate their progress. He also co-founded the Chicago Product Alliance to elevate general product practices across the community.

How to attend

This is a free, invite-only event for senior product leaders—but space is limited.

If you’re currently working in product and hold a Director, VP, CPO, or equivalent leadership role, this event is for you.

To request your place, simply complete the registration form in full. Each submission will be reviewed by our team to ensure we’re creating a high-quality, peer-level experience.

Please note:

• Every application is reviewed individually
• MTP reserves the right to cancel any registrations if the attendee’s role or experience does not match the level outlined above or as explained on the ticket page

This process helps ensure meaningful conversation and connection among true peers.

Thank you to our sponsors

ITX: For nearly 30 years, ITX has solved complex business challenges through custom software products that drive lasting value for our clients. Our approach—focused on experimentation, learning, and growth—builds enduring partnerships and transformative products, powered by a culture of global collaboration.

Drive Capital: Drive Capital is a venture capital firm founded in 2013 and based in Columbus, Ohio. With over $2 billion under management, the firm invests in early-stage and growth companies outside of Silicon Valley—primarily across the Midwest and other emerging innovation hubs. Drive backs visionary founders building transformative businesses in technology, healthcare, consumer, and financial services, with a mission to create and scale world-class companies in regions often overlooked by traditional VC.