Embracing Innovation in the Enterprise: Key Takeaways from the Midwest

By Rich Scudellari


This week, Penny Jar hosted Innovation in the Enterprise in Milwaukee, an event focused on how technological transformations are reshaping large companies. The panels, discussions, and questions around innovation in the enterprise were vibrant, the insights were profound, and the enthusiasm was palpable. We were fortunate to bring Penny Jar founders together with industry leaders from the Midwest to share their perspectives. We combined that with an equally thoughtful audience, providing a curious sounding board. Though we could fill a novel with insights from the day, here are three main takeaways from the day.

The Midwest’s Quiet Drive for Innovation Can’t Remain So Quiet

One of the most heartening observations was the robust appetite for innovation in the Midwest. There’s an undeniable drive here, characterized by a unique blend of humility and determination. Unlike the more vocal innovation hubs on the coasts, Midwestern companies and individuals often prefer to keep their heads down and push forward rather than broadcasting their achievements. This admirable trait, however, can sometimes be a double-edged sword. Finding a balance where we can celebrate and communicate our advancements without losing that quintessential Midwest humility is crucial. There’s so much happening here that deserves recognition, and by sharing our successes, we can inspire further innovation and collaboration.

penny jar FOUNDING partner rich SCUDELLARI with permanent capital founding partner mike gamson.

Attracting AI Talent Goes Beyond the Paycheck

Compensation isn’t the sole determining factor in the competitive landscape for AI talent. While some outrageous comp packages get headlines, as Kyle Langworthy from Riviera Partners highlighted, the best talent is drawn to challenging problems, intriguing data, and environments that foster creativity and impact. Companies without the budget of tech giants like Alphabet, Meta, or Microsoft can still attract top-tier talent by focusing on what they uniquely offer. This includes the complexity of problems to solve, the quality of data available, and the potential for meaningful work. It’s about creating an ecosystem where talented individuals can thrive and feel valued for their contributions.

rich scudellari speaks with kate woodward (ge aerospace) and charlie Franklin (Compa) on being an employer of choice.

AI Is Not Replacing Humans; It’s Changing Job Requirements

There is a significant concern among many that AI is coming for all of our jobs. But like many prior platform shifts (e.g., computers, the internet, mobile, etc.), it’s simply changing the job requirements. For example, computers did not replace humans; instead, they have turbo-charged what we can achieve. We should expect the same from AI. It will not replace us; yes, AI will require a new set of skills, but it will expand what we can achieve as many past platform shifts did.

We at Penny Jar are excited to have incredible partners in places like Milwaukee and fortunate to have boots on the ground in such a vibrant, innovative part of the country. Our unique position of having a foot in the Bay Area and the Midwest gives us an appreciation for the similarities and differences between the two parts of the country. What is clear is that there is a voracious appetite for pushing the boundaries of innovation, and we look forward to finding more opportunities like this one to continue bringing like minds together, wherever they may be located.

the penny jar capital teaM (from L TO R): Rich scudellari, vrinda agarwal, bryant barr.

Thank you to our partners Riviera Partners, Quarles, and Citizens Private Bank for their invaluable collaboration in making this event a success. We would also like to offer our deep gratitude to the speakers and guests for sharing their insights, curiosity, and perspective, resulting in an engaging and enlightening discussion for all.