In this episode of Innovation and the Digital Enterprise , Patrick and Shelli chat with Steve Gall, CTO of M1 Finance, a personal finance platform. Steve talks about his journey helping scale M1 from a few engineers to a platform managing over $10 billion in client assets. Steve shares insights about the ways that he and M1 have managed risk, navigated compliance in this highly regulated industry, and deftly adjusted technical strategies during rapid growth. Steve highlights a commitment to cent...
Jul 24, 2025•39 min•Ep. 131
In this episode, Patrick and Shelli chat with Bill Himmelstein, founder and CEO of the Tenant Advisory Group, a tenant-focused commercial real estate brokerage in Chicago. Bill shares his journey from the early influence of his real estate investor father, to his accidental but fortuitous entry into the world of commercial real estate, including his initial struggles and eventual success. Emphasizing a tenant-first philosophy, Bill discusses his commitment to always seeking the best deals for hi...
Jul 10, 2025•37 min•Ep. 130
In this episode Patrick and Shelli welcome Michael Pozzi, a tech leader with an expansive career across engineering, computer science, and finance. Currently, Michael is Senior Vice President of Technology Infrastructure at Ryan Specialty. We discuss Michael's leadership style, a philosophy characterized by humility and a team-centric approach. He shares his experiences of leading through uncertain times at the Chicago Mercantile Exchange, and highlights the ways he builds teams to foster empath...
Jun 19, 2025•41 min•Ep. 129
In this episode of Innovation and the Digital Enterprise, Patrick and Shelli talk to Jeff Miller, Vice President of Engineering at LinenMaster. Jeff discusses his journey in the tech industry and his role at LinenMaster, a leading laundry management solutions provider. He delves into his previous roles at various prominent Chicago technology companies focusing on his work to modernize platforms and streamline operations. We talk about his earlier interest in tech; he built a computer when he was...
Jun 05, 2025•30 min•Ep. 128
In this episode Patrick and Shelli talk with Firasat Hussain, the Chief Product and Technology Officer at SnapCare. Firasat shares his 25-year journey through various technology leadership roles at companies like Ticketmaster, Orbitz, and RR Donnelley, emphasizing the significance of thoughtful leadership and iterative innovation. He describes his transition to SnapCare, where he is leading the integration of new AI tools and modern tech stacks to transform healthcare staffing. The discussion de...
May 22, 2025•43 min•Ep. 127
In this compilation episode, we look back on wisdom from renowned tech executives about how to build and foster great teams. Featuring insights from Fred Lee, Dan Kirsche, Jorie Sax, Steve Caudill, Christina Garcia, and Dom Scandinaro, who share their perspectives on the importance of diverse and well-structured teams. Key topics include team composition, sharing knowledge, effective scaling, fostering interpersonal relationships, and creating rich organizational culture. These leaders emphasize...
May 08, 2025•17 min•Ep. 126
At the start of last year, we had a really inspiring conversation with Chris Brown and are excited to reshare it this year, in our “Best Of” series. Originally published 01/25/24. An exceptional company culture builds when steadfast employee commitment meets deep trust by customers. Chris Brown encountered this when he joined Relativity as Chief Product Officer in 2018. Chris joined the team in the early stages of their transition to SaaS and embraced the moment of disruption and opportunity—a f...
Apr 24, 2025•28 min•Ep. 125
In this episode, we look back on invaluable leadership insights shared by renowned executives across the technology industry. Featuring wisdom from Christine Sandman Stone, Arne Saupe, Jorie Sax, Thulasi Kethini, and Tony Newcome, the discussion delves into the distinct skill sets required for leadership, the importance of fostering a culture of innovation, and the critical need for supportive and open communication within teams. These leaders unpack practical advice for setting meaningful goals...
Apr 10, 2025•15 min•Ep. 124
Today, Patrick and Shelli are joined by Toner Babovac, the Technology Managing Director and Senior Location Executive at IBM. In our chat, Toner delves into his long career at IBM and how building trust has allowed him to drive innovation while coordinating a large team. He highlights the role of effective communication, in particular the importance of video calls and in-person meetings for fostering a strong team culture, especially in a hybrid work environment. Toner also shares his approach t...
Mar 27, 2025•40 min•Ep. 123
In today’s episode Patrick and Shelli welcome Jay Topper, Chief Customer Officer at Fabric, to discuss his extensive career, leadership practices, and retail trends in 2025. In our wide-ranging discussion, Jay emphasizes the importance of curiosity, self-awareness, and a 'hero culture' within organizations to foster quick and effective change. As an advocate for rapid execution and overcoming complacency, he offers practical advice for leaders to push their teams, but not push them away. Jay unp...
Mar 13, 2025•51 min•Ep. 122
In this episode of Innovation and the Digital Enterprise, Patrick Emmons and Shelli Nelson chat with Ben Rogers, the President of TydenBrooks, a global leader in the manufacture of tamper evident safety and security seals. Ben has had a notable career at Madison Industries, primarily focusing on growth and strategic acquisitions. Ben unpacks his roles, specifically discussing his customer focused approach to innovating tamper evident products. He explains the importance of providing tamper evide...
Jan 09, 2025•22 min•Ep. 121
In this episode of Innovation and Digital Enterprise, we sit down with Michael Lambert, Chief Innovation Officer at Wintrust Financial. Michael discusses his role in driving innovation and technological advancements within Wintrust, focusing on the significant growth and transformation he has witnessed during his tenure. We chat about strategies for leveraging data to make informed decisions, and about the fundamental importance of building strong relationships to fostering a supportive workplac...
Dec 19, 2024•29 min•Ep. 120
In this episode of the Innovation and the Digital Enterprise, Shelli and Patrick chat about industry advancements and leadership with Deepak Kaimal, Chief Technology Officer at COMPLY. He was previously CTO at Exostar, and held that role when this episode was recorded. Exostar, founded in 2000 by industry leaders like Boeing, Raytheon, and Lockheed Martin, provides secure collaboration and risk management solutions to the defense and life sciences sectors. Deepak shares his journey from an engin...
Dec 05, 2024•31 min•Ep. 119
Today we talk with Jeff Miller, Chief Product Officer at Coates Group, about his extensive experience in retail and restaurant technology, emphasizing the role of digital transformation in enhancing customer and employee experiences across Quick Service Restaurants (QSRs). We explore the integration of digital and in-store experiences, the significance of mobile ordering and loyalty programs, along with the challenges of managing a complex partner ecosystem. Looking forward, Patrick, Shelli, and...
Oct 31, 2024•29 min•Ep. 118
On today’s show, we chat with Kal Walkden, the Vice President of Product Engineering at Double Good . Double Good’s virtual fundraising app connects teams with their supporters to help athletes, coaches, and students raise funds through popcorn sales. Focusing on seamless ease-of-use for both the fundraisers and their supporters, Double Good turns online snack sales into “uniforms, safety pads, cleats, calculators, test tubes, travel opportunities, and brand new experiences.” Kal's extensive exp...
Oct 17, 2024•27 min•Ep. 117
“It’s marketing through people instead of at them,” says Emily Steele, CEO and Co-founder of Hummingbirds. In this episode of Innovation and the Digital Enterprise we talk with Emily about how Hummingbirds is leveraging hyperlocal content creators to drive brand awareness and sales. Emily shares her journey from running a local marketing agency to founding Hummingbirds, emphasizing the power of word-of-mouth marketing and community-driven content. She explains Hummingbirds’ unique approach of fo...
Oct 03, 2024•33 min•Ep. 116
Wouldn’t it be great if your boss had a user guide for achieving success under their leadership? Ann Yeung’s team at GEICO , where she serves as the Vice President of Engineering, Head of Enterprise Engineering, received one. In her “user guide,” Ann shares her expectations, values, and tools for successful collaboration that go well beyond pet peeves to establish communicative, empowered teams. In this episode, Ann discusses her transition to GEICO and the critical role of managing corporate fu...
Sep 19, 2024•38 min•Ep. 115
Does the “I don’t know how we’re gonna do this?” feeling ever fade? In large-scale transformation, Megan Williams, VP of Global Technology Strategy and Transformation at TransUnion , doesn’t think so. Leading global, multi-year transformation programs continues to prompt the major questions: What is our vision? What is the approach? With over 20 years of experience, the initial intimidation remains, but Megan and her teams persist. In this episode, Megan shares how guiding TransUnion’s transform...
Sep 05, 2024•31 min•Ep. 114
Out of approximately 5,000 lending institutions nationwide, Srikanth Geedipalli and the team at Experian have developed relationships with 3,000 of them, and the list continues to grow. As Senior Vice President of AI Product Management and Commercialization, Srikanth is spearheading the productization and democratization of data. In this episode, Srikanth explains how he promotes innovation at Experian, accounting for its size, role as a trusted brand, and regulated and compliance-oriented proce...
Aug 22, 2024•38 min•Ep. 113
Sticky notes might be the key to successful leadership. Christina Garcia, Senior Vice President of Engineering at Echo Global Logistics , keeps a few posted nearby with essential reminders to guide her in difficult moments. When leading teams of engineers attempting to disrupt the logistics space grows challenging, having a reminder of foundational leadership tools can be the key to accurately identifying an issue and swift resolution. In this episode, Christina discusses determining what to bui...
Aug 08, 2024•37 min•Ep. 112
Joining a new company and being tasked with adding value and building high-performing teams starts with one key question: what is the organizational structure? Experienced technology leader Dan Kirsche has recently joined Chamberlain Group as the Senior Vice President of Software Engineering after a robust career of leading software engineers. With innovation and team building on his mind, Dan shares key lessons in culture-creating behaviors, embracing disagreement, and successful leadership. In...
Jul 25, 2024•38 min•Ep. 111
At the start of summer last year, we had a really inspiring conversation with Christopher Paquette and are excited to reshare it this year, in our “Best Of” series. Originally published 06/29/23. Tasked with accelerating digital transformation at Allstate , Christopher Paquette recognizes the digital potential embedded everywhere. Reflecting on his first year as Chief Digital Transformation Officer at Allstate, Christopher shares essential lessons in collaboration, creating value for the custome...
Jul 11, 2024•31 min•Ep. 110
We had a fascinating conversation with Deborah Spence-Cummings in late 2022 and are excited to reshare it in our “Best Of” series. Originally published 12/01/22. Only an exceptional innovator would look at a burgeoning career in operations and pause to examine their reputation and evaluate their goals. With the help of an executive coach, Deborah Spence-Cummings did just that and now serves as the Director of AI/ML Operations at Apple . Deborah shares how she used an engineering mindset develope...
Jun 27, 2024•40 min•Ep. 109
OKRs are easy to set up badly. Christine Sandman Stone, CEO and founder of Deliver at Scale , focuses on this key element for success based on her years leading agile transformations. Beginning with her journey, Christine shares her path to leadership and the critical lessons she’s learned—and shared—along the way. In this episode, Christine provides a glimpse into her world guiding teams to hone in on their goals. First, she offers her perspective on setting the objective and determining the qu...
Jun 13, 2024•38 min•Ep. 108
Should we look beyond technology organizations to learn essential lessons on how to innovate and run successful, complex technology organizations? Gene Kim believes so and contains unbridled curiosity for transformation across industries, as seen in his most recent book Wiring the Winning Organization . Gene Kim returns to share new lessons in change-making for leaders and companies tackling an array of challenges. Gene Kim is a bestselling author of several books on technology innovation, DevOp...
May 30, 2024•39 min•Ep. 107
We had a great conversation with David Heinemeier Hansson in 2023 and are excited to reshare it in our “Best Of” series. Originally published 11/2/23. Profound innovation has occurred across web-based communication technologies in the last decade, and truly accelerated in the years since the start of the pandemic. But David Heinemeier Hansson recognized a massively neglected arena, one we all use, every day: email. Bringing his experience as co-owner and Chief Technology Officer at 37signals ( B...
May 09, 2024•53 min•Ep. 106
Today we're sharing another insightful presentation from our most recent Innovative Executives League Summit , where Leon Chism, the Vice President of Engineering at Evolve , delivered a powerful lesson on collecting critical metrics for organization-wide success. As an experienced technologist and executive, Leon leads teams in unparalleled growth and innovation. In this presentation, Leon dives into how the collection of metrics examining speed and quality paired with human-driven evaluation a...
Apr 18, 2024•31 min•Ep. 105
Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit , where Tanya Hannah discusses the roadmap to navigate the ever-evolving tech landscape. As a seasoned transformational business executive, Tanya offers the pillars needed to survive major shifts and thrive in the opportunities presented by them. In this episode, Tanya shares how critical a shared vision and strategy is in preparation. Teams cannot operate only with yesterday’s logic; the...
Apr 04, 2024•28 min•Ep. 104
Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit , where Desiree Vargas Wrigley, Chief Innovation Officer of P33 Chicago and Executive Director of TechRise by P33 , delivered a lesson in stakeholder-centric design. Desiree overviews the challenges Chicago’s underrepresented tech founders face and the process of developing TechRise’s initiatives. Highlighting the impact of TechRise and P33, Desiree presents a galvanizing picture of Chica...
Mar 21, 2024•27 min•Ep. 103
Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit , where Maya Mikhailov, Chief Executive Officer and founder of SAVVI AI , discusses machine learning as a powerful toolkit of solutions. Comparing efficiency with and without AI, she highlights how the proper tool makes the difference and cuts through assumptions. Is Chat GPT the AI tool that makes Amazon such a success? No. It is Amazon's recommendation engine built on billions of data p...
Mar 07, 2024•24 min•Ep. 102
