Innovation and the Digital Enterprise

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.

In his role as Vice President of Enterprise Architecture and Technology Strategy at Aon, Mohan Putcha’s job is to be ahead of the curve in spotting technology trends and understanding how they’ll impact the industry.

It is also about leveraging those trends to deliver better service for Aon’s clients and internal teams, not just in theory, but in practice. Which is why Mohan’s team has taken a different approach to building platforms – one that starts by looking at the full value stream and understanding the real pain points of the people contributing to each piece of it.

This week, Mohan joins Patrick and Shelli to discuss this people-centered approach to building platforms, how to keep your team engaged while accelerating innovation, and his take on the biggest challenges of 2022.

Technology is about solving problems and building solutions. This week’s guest, Sandee Kastrul, recognized the overlap in competencies needed for both technology and community leadership when she co-founded i.c.stars. This week she talks with Pat and Shelli about teaching technology with systems thinking, a community-lens, and an orientation of ‘how can I help’ versus ‘what can I get’.

For more than two decades, i.c.stars has been developing tech talent in Chicago through a rigorous four month curriculum rooted in midwestern practicality and centered in resilience. Each cycle, a new cohort of interns is divided into teams to form their own consulting companies to compete in an RFP process for a Chicago tech company. It’s not a drill, these are real projects and the teams are building real software. It is an immersive, hands-on approach that has fueled the program's continued success with a 90% graduate placement rate.

Listen in to hear more about the transformative power of the i.c. stars community and how to take part by signing up for the next High Tea.

Rand McNally’s Chief Technology Officer, Steve Caudill, joins Patrick and Shelli this week to talk about building and maintaining the culture of a startup inside a well-established brand with a 165-year history. They cover a range of topics including recruiting talent in a highly competitive market, creating tight feedback loops between customers and engineers, and structuring product development for the shortest path to revenue.