In this special compilation episode of Innovation and the Digital Enterprise, Patrick Emmons highlights key insights on digital transformation from top tech leaders. Featuring perspectives from Andrei Girenkov, Christopher Paquette, Ann Yeung, Sandee Kastrul, Deepak Kaimal, Jeff Miller, Christina Garcia, Tanya Hannah, Dan Kirsche, Dom Scandinaro, Subramanian Kunchithapatham, and Gene Kim. The episode delves into leading transformative tech teams, balancing disruption and protection, the role of AI, the need to stay nimble, and the foundational significance of human connection and communication in achieving successful digital transformation.

• (00:00) Welcome to Innovation and the Digital Enterprise
• (02:17) Andrei Girenkov Understanding the Scope of Digital Transformation
• (03:17) Christopher Paquette on Balancing Protection and Disruption
• (04:00) Ann Yeung on The Role of Corporate Functions
• (04:52) Sandee Kastrul on Diversity and Innovation
• (05:22) Deepak Kaimal Leveraging Gen AI for Business Solutions
• (07:01) Jeff Miller on  Navigating Technological Change
• (07:21) Christina Garcia on Empowering Teams
• (07:59) Tanya Hannah on Keeping Nimble
• (08:28) Dan Kirsche on Org Structure and Accountability
• (09:17) Dom Scandinaro on Growth, and Agility
• (10:10) Subramanian Kunchithapatham on the Challenges of Digitization
• (10:53) Gene Kim on Connecting People Through Norms, Rituals, and Processes

Andrei Girenkov is Chief Technology Officer at CSC Service Works. Christopher Paquette is Chief Transformation Officer at Personify Health. Ann Yeung is VP of Engineering at GEICO. Sandee Kastrul is President and co-founder of i.c.stars. Deepak Kaimal is Chief Technology Officer at COMPLY. Jeff Miller is Chief Product Officer at Coates Group. Christina Garcia is SVP of Engineering at Echo Global Logistics. Tanya Hannah is Chief Information Officer at OneTen. Dan Kirsche is Chief Technology Officer at Chamberlain Group. Dom Scandinaro is Chief Technology Officer at Cameo. Subramanian Kunchithapatham is Vice President - BI Solutions at Morgan Stanley. Gene Kim is an author, researcher, and founder of Tripwire, Inc.

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In this episode of Innovation and Digital Enterprise, Patrick and Shelli interview Adan Pope, Senior Vice President of Engineering, Applications, and AI at The Aspen Group. Adan shares insights from his career in engineering and technology leadership, from his roles in public safety, telecommunications, and healthcare. He also discusses his books, “Respect the Weeds” and “Intentional Tensions”, which reflect on principled leadership and effective digital transformation strategies. He emphasizes the importance of humility, continuous learning, and building teams that thrive on productive tension. Adan unpacks the ways he drives innovation, and how engineering teams can balance velocity with stability, while maintaining high standards of quality.

• (00:00) Welcome Adan Pope
• (02:21) Early Career and Influences
• (04:37) Leadership and Innovation
• (07:35) Writing 'Respect the Weeds'
• (11:30) Intentional Tensions in Leadership
• (19:42) Building Effective Teams
• (21:46) Navigating Human Dynamics in Teams
• (22:22) The Importance of Positive Tension
• (22:56) Lessons from Bell Labs
• (24:47) Balancing Sales and Engineering Goals
• (29:00) Fostering Ownership and Pride in Work
• (33:18) The Power of Visual Communication

Adan Pope is a technology executive, professor, and published author and speaker, currently the Senior Vice President of Engineering Applications and AI at The Aspen Group. He also is an Adjunct Professor at the Illinois Institute of Technology teaching in the graduate Information Technology Management Department. He is the cofounder of Taraxa Labs LLC, providing workshops, consultancy practical tools, and guidebooks to help leaders navigate digital transformation. Previously he has held roles at Intrado Life & Safety, InnerWorkings, Ciena, ShopperTrak, Ericsson, Telcordia Technologies, and Bell Labs. He earned a BSEET at DeVry University and a MCS and MBA from North Central College.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

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In this episode of Innovation and the Digital Enterprise, Patrick Emmons and Shelli Nelson welcome Sean McCormack, Chief Innovation Officer at First Student. They discuss his career that spans military intelligence, startups, global enterprises, and now tech-focused leadership in student transportation. Sean shares his unexpected entry into technology through the development of early online language learning systems in the military which later led to diverse experiences across industries.

Today, at First Student, Sean has spearheaded digital transformation initiatives to modernize student transportation. He discusses the complexities of managing a large fleet, the challenges of tech integration, and highlights the use of AI in supporting recruiting and enhancing safety.

Sean unpacks his leadership philosophy, emphasizing the need to understand the day-to-day, improve communication, and build strong, delivery-focused teams. He shares valuable lessons on driving innovation, managing change, and leading with empathy and effectiveness.

• (00:00) Introduction
• (01:46) Sean McCormack’s Career Journey
• (03:49) Impactful Experiences and Lessons Learned
• (05:58) Innovating at Harley Davidson
• (09:26) Transforming First Student with Technology
• (16:11) Implementing AI at First Student
• (22:40) Leadership and Communication Insights
• (28:43) Advice for Future Technologists and Leaders
• (32:45) Conclusion and Final Thoughts

Sean McCormack is the Chief Innovation Officer at First Student, the largest provider of student transportation services in North America. Previously, he’s held leadership positions at Grainger, Harley-Davidson and ManpowerGroup. He earned his BA at the University of Texas at Austin, and his Executive MBA at the University of Wisconsin-Milwaukee.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

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 centering the user, providing a safe, stable, trustworthy experience even in the midst of a shifting fintech landscape, and while his company was quickly scaling. He shares the challenges, the opportunities, and the strategies involved in growing the M1, stressing the importance of resilience, empathy, and adaptability in leadership. The conversation closes with a chat about Steve’s passion for pinball and a great list of his recommended reads for CTOs.

• (00:00) Welcome Steve Gall, CTO of M1 Finance
• (01:32) Steve’s Background and Role at M1 Finance
• (04:26) Childhood Investment Interests
• (07:23) The Concept Behind M1 Finance
• (13:16) Regulatory Challenges and Growth
• (16:33) Transition to Self-Clearing Broker Dealer
• (20:33) Achieving Hockey Stick Growth
• (23:09) Navigating Organizational Challenges
• (25:24) Scaling and Downsizing
• (28:03) Handling Workforce Reductions with Empathy
• (31:53) Pinball, Personal Insights and Recommended Reads
• (38:08) Closing Thoughts

Steve Gall is the Chief Technology Officer at M1 Finance. He serves on the board at B2 Bank and is involved with P33 Chicago. Past roles include Technical Architect at Avionos LLC, and Senior Associate at Acquity Group (part of Accenture Interactive). He started his career at Alcon Labs after earning a Bachelors in Computer Science at Purdue University.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

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 his clients, even when they are ready to accept current offers. He highlights the importance of honest relationships, exceeding client expectations, and treating other people’s money with the same respect as one's own. 

Bill shares his advice for entrepreneurs, stressing the importance of valuing one’s time and building genuine, mutually beneficial relationships. Throughout the discussion, Bill demonstrates an authentic passion for helping others, and shares ways to leverage relationships to maintain a client-first approach in business.

• (00:25) Introducing Bill Himmelstein
• (01:57) Bill's Early Influences and Real Estate Journey
• (07:17) The Importance of Sales Skills in Entrepreneurship
• (11:18) Building Trust and Relationships
• (16:31) Tenant-First Philosophy and Client Success Stories
• (19:13) Building Long-Term Client Relationships
• 22:54 Current Trends in Chicago's Office and Industrial Markets
• (30:24) Entrepreneurial Lessons Learned
• (33:57) The Value of Making Connections

Bill Himmelstein is founder and CEO of the Tenant Advisory Group, a tenant-focused commercial real estate brokerage focused on helping tenants, buyers, and sellers get the most out of their business’ space. In the past, he’s held roles like Managing Director at Advocate Commercial Real Estate Advisors; Broker at the John Buck Company; and Senior Associate at Cushman & Wakefield. He earned a BSBA from Washington University in St. Louis.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

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 empathy and collaboration. We chat about the evolving landscape of technology infrastructure, data volume, AI automation, and the dynamics of remote teams. Michael advocates for recognizing and nurturing talent within an organization, fostering an environment where employees can thrive and grow in alignment with their org’s mission.

• (00:00) Welcome Michael Pozzi
• (00:25) Michael’s Career Journey
• (02:26) Role at Ryan Specialty
• (03:07) Early Career and Pivot to Consulting
• (05:01) Joining the Chicago Mercantile Exchange
• (08:50) Transition to Infrastructure and Operations
• (12:51) Leadership and Team Dynamics
• (21:47) Recognizing the Need for Fresh Perspectives
• (24:05) The Importance of Empathy in Team Dynamics
• (29:06) Career Growth and Organizational Support
• (34:48) Encouraging Internal Mobility and Learning
• (40:10) Final Thoughts

Michael Pozzi is Senior Vice President of Technology Infrastructure at Ryan Specialty. Previously, over nearly 20 years, he held a series of director level positions at the CME Group, like Managing Director of Infrastructure & Operations, Executive Director of Systems Engineering, and Executive Director of Software Engineering. Before that he worked at Hewitt Associates and Accenture. He earned a Bachelors degree in Mechanical Engineering from Duke and Masters in Computer Science from DePaul.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

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 a kid. Then Jeff shares insights into this hands-on approach, the challenges of transforming legacy systems, and the importance of iterative development. He discusses his leadership philosophy of roadmapping transformation with the customer in mind, and building trust through execution.

• (00:00) Introducing Jeff Miller, VP of Engineering at LinenMaster
• (01:14) Jeff Miller's Career Journey
• (04:38) Roadmapping Strategy at LinenMaster
• (06:24) Technological Transitions and Innovations
• (09:36) Leadership and Decision-Making
• (09:37) Jeff's Early Interest in Technology
• (12:58) Rebuilding Trust and Modernizing Software
• (25:02) Advice for Tech Professionals and Founders
• (28:47) Conclusion and Farewell

Jeff Miller is Vice President of Engineering at LinenMaster. Previously he moved up through a variety of roles at Yello.co culminating in a position as Chief Technology Officer. Before that he was Vice President Of Engineering at Fooda and he launched his career at Enova International. He earned a Bachelors degree in Computer Science and Mathematics from the University of Wisconsin-Madison, where he was also President of the Madcity Skydiving Club.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

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 delves into Firasat’s leadership philosophies, the importance of trust and influence over demands, and his commitment to growth and learning, both personally and professionally.

• (00:00) Welcome to Firasat Hussain, CPTO at SnapCare
• (01:23) From Accounting to Technology: Firasat's Early Career
• (04:32) Transition to Healthcare Tech: Joining SnapCare
• (05:26) The Role of Technology in Healthcare Staffing
• (07:11) Personal Insights: Leadership and Growth
• (12:03) The Importance of Travel and Broader Perspectives
• (14:41) SnapCare's Mission and Operations
• (20:13) Balancing Leadership in Work and Family Life
• (24:18) The Power of Trust and Kindness Over Demands
• (27:07) Building Trust Through Honest Conversations
• (30:05) The Importance of Active Listening
• (32:23) Establishing Priorities and Reducing Cognitive Overload
• (37:59) Reflecting on Personal and Professional Growth
• (41:50) Final Thoughts

Firasat Hussain is the Chief Product and Technology Officer at SnapCare, a technology-driven healthcare staffing firm. His 25+ year career has spanned varied industries and organizations at a range of stages, from established global tech firms to promising startups. He was Chief Technology Officer at arrivia, VP of Software Engineering at Ticketmaster, and VP of Enterprise Architecture at RR Donnelley. He spent 10 years growing and leading at Orbitz Worldwide, with six years as Director of Hotel Product Development. He launched his early career at Cysive and Oracle.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

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 the significance of nurturing talent and fostering diversity to build world-class teams capable of overcoming challenges and driving innovation.

• (00:00) Introduction to Building Teams
• (01:39) Fred Lee knows that great teams will naturally build great products
• (02:42) Dan Kirsche on building teams with complementary skills
• (03:07) Jorie Sax recommendations team-driven ideation
• (03:42) Steve Caudill champions diverse teams
• (04:17) Christina Garcia on owning and communicating mistakes
• (05:32) Jorie Sax discusses the balance of structure and freedom
• (06:57) Dom Scandinaro on scaling teams and workflows
• (07:59) Dan Kirsche on coaching to a teammate’s skillset
• (08:42) Jorie Sax unpacks interdepartmental communication
• (10:34) Christina Garcia on having a great culture
• (12:39) Fred Lee on cross-department connections
• (14:04) Dan Kirsche explains how he both challenges and supports his team
• (16:03) Christina Garcia reminds us to be in service of your team

Fred Lee is CTO at PartsSource. Dan Kirsche is the newly promoted CTO at Chamberlain. Jorie Sax is head of United Airlines Innovation Lab. Steve Caudill is former CTO at Rand McNally. Christina Garcia is SVP of Engineering at Echo Logistics. Dom Scandinaro is CTO at Cameo.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.

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 familiar territory in his career, which included ten years at Orbitz Worldwide. From the perspective of CPO, Chris offers unique insights into the transition period from on-prem to SaaS, addressing legacy technology, embracing the customer as a co-innovator by building plentiful touchpoints, and the intricate SaaS sales process. Speaking on what SaaS can inimitably provide, Chris muses on “a continuous stream of innovation at high availability” and customer success.

In this episode, Chris looks ahead to the future to discuss how AI and LLMs will impact the law industry and finding effective uses for the technology. He shares how one of the oldest industries in the world can embrace the best of AI’s capabilities while mitigating the risks by including the law's critical element: human decision-making and validation.

With experience as a CEO and CPO, Chris shares the distinctions between the roles that stem from the needs of a particular company and offers how his arrival at Relativity reflected intentional scaling that led to further success. In discussing the Chicago startup environment and continued growth at Relativity, Chris talks about acquiring the contract review company Heretik and considering an acquisitive approach as one path of innovation and building a strong product portfolio. 

• (02:24) – Introducing Chris Brown
• (04:56) – CPO vs. CEO
• (06:30) – Sales in the SaaS world
• (08:59) – Relativity
• (10:58) – Building an effective SaaS company
• (15:43) – Co-innovating with customers
• (17:59) – AI and the law industry
• (22:18) – Looking ahead
• (23:59) – An acquisitive approach

Chris Brown is the Chief Product Officer at Relativity, a cloud review software that helps users “organize data, discover truth, and act on it.” Previously, he served as Senior Vice President and Chief Product Officer at Orbitz Worldwide and CEO and Board Member of Kapow! Chris earned a bachelor's degree in computer engineering from the University of Illinois Urbana-Champagne.

If you'd like to receive new episodes as they're published, please subscribe to Innovation and the Digital Enterprise in Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.

Podcast episode production by Dante32.