Innovation and the Digital Enterprise

When Tommy Richardson enlisted in the United States Army at 18, he narrowed his options to operating a tank or going into computer operations and programming. In selecting the latter, he launched a lasting career in the field, has led several major companies in C-suite positions, and recently arrived as Chief Product and Technology Officer for Litmos, leading product innovation.

Between confidentiality agreements, polite manners, and ego, it can be difficult to get a real story of what selling a company is like. Breaking that taboo was the inspiration for Exit Right, a book co-authored by today’s guest Mark Achler, Managing Director at MATH Venture Partners.

One consequence of success for a startup is outgrowing the very strategies that made you successful. As an experienced founder, it’s a challenge Justin McNally was prepared to tackle as Chowly grew from a seedling idea to a market leader in point-of-sale integration. At each stage of growth, Justin’s role, and sometimes title, evolved to meet the changing needs of the organization.

The Innovative Executives League recently held its second in-person summit with an amazing slate of thought leaders sharing their experiences and perspective on innovation and leadership. In this episode, Patrick and Shelli highlight a variety of insightful presentations from the event.

A great teacher can be the key to welcoming challenges, self-confidence, and a curious spirit. In the case of Larry Berlin, Chief Financial Officer at Freedom Fries, great teachers also inspired a lifelong commitment to mentorship, including his critical mentor role for the New Venture Challenge, an accelerator program that has launched Grubhub, Braintree/Venmo, and many more successful companies.

A fresh spotlight is on clinical research on account of the COVID-19 pandemic. Katherine Vandebelt, Global Vice President of Innovation at Oracle, shares how she is innovating clinical research participation through inclusive, accessible, and human-centered practices.

Sometimes a simple desire to give back can lead to unexpected places. That’s what happened when Jay Rudman decided to help other entrepreneurs in the Chicagoland community after selling his last business. What started as a semi-formal coaching relationship with the founder of Topstep, eventually led to Jay stepping in as Chief Growth Officer and eventually CEO, a role he held until recently.

In this episode, Jay talks about his entrepreneurial journey prior to Topstep, one that started all the way back in high school running lawn care services. He also walks Patrick and Shelli through the specifics of the Topstep community and how retail traders can practice their skills in a safe environment before trading with real capital.

At TransUnion, creating innovative products, building talent, and delivering excellent customer experiences start with an environment where trust is possible. Swati Shah, U.S. Markets CIO, talks with Patrick and Shelli this week about what cultivating that trust looks like for the organization.

She also describes the various programs in place to support continuous learning for cross-functional teams and the importance of helping engineers understand the ‘why’ in addition to the ‘what’ for the solutions they are building.

Experiencing a sudden revenue drop is a formidable challenge for any business. When SpotHero found themselves there at the start of the pandemic, the team took it as an opportunity to pause and rethink their business.

In this episode, Matt DiBari, Chief Product Officer at SpotHero, talks with Patrick and Shelli about how creative thinking and a strong team foundation allowed SpotHero to weather the sudden downturn. He also discusses how a culture of looking around corners and reacting with wonder fuels innovation both today and for the company’s ‘horizon 3’ plans.

Innovation starts when all stakeholders are working as a cohesive unit and have identified a common mission. Matt Kelly, a partner and Business Designer at Do Tank, is our guest this week. Matt believes that to be successful, a company needs to spend time doing business modeling that allows them to increase efficiency and ensure they are targeting the right customer demographics.