Innovation and the Digital Enterprise

Extended reality has Jack King animated about innovation and the future of technology. As Chief Information Officer at the American Academy of Orthopaedic Surgeons, Jack sees the countless ways that augmented and virtual realities can accelerate learning and opportunities for the 39,000 members of AAOS.

In this episode, Jack discusses motivation, connection, and encouraging employees to be participants in driving change. He speaks on company culture and his approach to communication, including daily huddles. While sharing his excitement over continuing technological innovations, such as haptic feedback, Jack reflects on lessons from his cross-industry career.

In addition to hosting Innovation and the Digital Enterprise, Pat is also the founder of the Innovative Executives League, a group that connects visionary Chicago leaders. Earlier this year, the group held its first in-person Innovative Executives League Summit with an amazing slate of leaders sharing experiences and perspectives on innovation and leadership. Today’s episode pulls together highlights from three of the day’s presentations.

Seeking professional advice to advance your career? Patrick Dineen, Chief Information Officer at Nielsen, has the answer: solve bigger problems. As a leader in strategic planning and transformational thinking within several major companies over his career, Patrick is perfectly positioned to witness the incredible value of team members who seek out challenges and take advantage of big opportunities to contribute.

In this episode, Patrick reflects on outside-in thinking and a growth mindset in the workplace. He shares insight into the value of building relationships and trust across companies. Patrick discusses his leadership style: influence over authority, a willingness to take the blame, and intentionality in seeking out ways to assist colleagues. Patrick illuminates the complex relationship of being present and planning for the future, and he expounds on the value of operating on a very familiar unit of time: one week.

Not many people are willing to call up their competitors and dive into discussions on improving the industry. Sara Rossio, Chief Product Officer at G2, talks about viewing competitors as partners and building trust internally by being transparent. With these strategies in mind, leaders can better collaborate with customers and vendors to help industries evolve.

In this episode, Sara talks about how she approaches product management at G2. She mentions the use of artificial intelligence to personalize data, moderate, and validate reviews to meet customer needs. She discusses her leadership style of providing frequent, direct, and actionable feedback and the importance of supplying context. Sara illuminates the key to her success in product management and how companies can remain competitive by staying curious.

It is all about the people, the process, and the technology for Mike Kennedy, VP of Technology, Enablement, and Strategy at CDW and U.S. Army veteran. Whether analyzing processes, recruiting and retaining great employees, and implementing new technologies, Mike is invested in holistic transformation.

In this episode, Mike Kennedy discusses the importance of “little i” innovation, motivating employees, and inclusion in decision-making. He shares insight into a VSOM approach and agile practices while diving into processes. Later in the episode, Mike reflects on hiring and training the right personnel, including military veterans, and connecting with talented people early in their careers.

Fred Lee, Chief Technology Officer at Amount, is skeptical of “culture fit.” In leading technology teams of various sizes and goals, he has welcomed team members who approach things differently, who embrace their unique perspectives, and has witnessed their added value across organizations. In his cross-industry career, a fresh perspective has often served him well.

In this episode, Fred shares insight into the shifting experience of banking and the industry’s digital innovations. He reflects on how he has approached new roles and how getting close to the customer is essential to understanding a company’s successes and failures. Fred illuminates the array of approaches to process and communication, and the importance of following through.

Edward Wagoner, CIO of JLL, acknowledges what many C-suite executives do not: leaders are human. In his 26 years at JLL, Edward has seen tremendous company growth—investment in data and proptech, the purchase of two AI companies, and a serious effort to recruit the highest-level data scientists—and he’s had to grow as well.

In this episode, Edward talks about innovating the ways that we work together (in digital and physical space) and building environments that suit meaningful collaboration. He shares insight into JLL’s expansion and investments, including their focus on sustainability. Reflecting on his own journey, Edward discusses the essential role vulnerability holds in personal and professional growth and the obstacles he’s overcome to lead with authenticity.

AeroPay founder Dan Muller embraced Chicago’s supportive entrepreneurial ecosystem to build his innovative payment processing business in 2017, and he is looking to return the favor. This week’s episode offers an insightful conversation about finding the resources and community needed to materialize an idea, the often-fraught scaling period of a company, and the importance of advocating for fellow entrepreneurs.

Dan Muller is a product-first founder dedicated to rethinking the collection and distribution of payments, but he is equally committed to building community within his company and beyond. With Pat and Shelli, Dan discusses hiring philosophies at different points of company growth and getting real about how people are going to use your product and integrate it into their systems. A proponent of connecting with other founders, Dan speaks on how to embrace others’ insights and feedback while you create your own path.

How do we learn from our failures? Kayne Grau, CEO of Uptake, reflects on the highs and lows of his career in this week’s episode dealing with authenticity, leadership, and staying open-minded in your career path. He shares advice to his younger self about finding balance and embracing the lessons that emerge in difficult moments.

Before joining Uptake, Kayne had a long career building brands and growing companies. He’s a self-described “product guy”, who relishes opportunities to engage with the people side of business, whether that is by getting face time with customers or picking up the phone each day to connect with team members. Listen in as Kayne joins Pat and Shelli to explore cultivating employee culture in a remote world and the idea that there is no set approach to being visionary.

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.