Innovation and the Digital Enterprise

In this episode of Innovation and the Digital Enterprise, Patrick and Shelli welcome Jolie Fleming, Chief Product and Technology Officer at IHG Hotels & Resorts, to discuss leading tech teams across a global, franchised hospitality ecosystem spanning 21 brands and nearly 7,000 hotels in 100+ countries. Jolie discusses her career journey, specifically what tools she brought and what challenges she met when moving from financial services to hospitality. She explains IHG’s combined tech team, which unifies product and dev to increase speed, predictability, and gives business context increased visibility. They discuss the ever-shifting role of AI in future planning. And Jolie shares three key strategic themes: helping hotels keep “heads in beds”, improving operational efficiency with new property management systems, and deepening guest engagement via a new CRM tied to IHG One Rewards.

• (00:00) Welcome Jolie Fleming, Chief Product and Technology Officer at IHG Hotels & Resorts
• (01:10) Jolie’s Career Journey from Finance to Hospitality
• (02:39) Understanding IHG’s Global Scale and Franchising
• (09:39) Jolie’s One Team Culture
• (16:58) Discussing Strategic Themes and AI
• (23:45) IHG’s Loyalty Rewards and CRM Personalization
• (27:17) How to Future Proofing for Change

Jolie Fleming’s career spans more than 25 years of leading transformative growth through product management and technology initiatives across fintech, hospitality, and consulting sectors. Currently, she is the Chief Product & Technology Officer at IHG Hotels & Resorts. Previously she spent nearly nine years at E*TRADE, as Managing Director of Investing, Digital Channels, and Banking and then Head of Digital and Client Experience. She earned her bachelor's degree from Northwestern University.

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Podcast episode production by Dante32.

In this episode of Innovation and the Digital Enterprise, Patrick Emmons and Shelli Nelson are joined by Mike Maresca, Chief Technology and Transformation Officer at Ulta Beauty. Mike delves into his career journey, highlighting his progression from consulting to leading a major technological transformation at Ulta. He discusses the critical components of Project SOAR, a multi-year effort that aligned teams, data, and platforms to enhance customer experiences both in-store and digitally. Mike emphasizes the importance of a strong guest-focused business-driven IT strategy, born of continuous learning and an innovation culture. He shares insights on Ulta's approach to AI, data centralization, and maintaining a customer-centric philosophy. With a focus on future growth and sustainability, Mike outlines Ulta's bold vision, which includes expanding into wellness and international markets, as well as scaling personalization and marketplace capabilities. Mike shares his advice for aspiring leaders: be bold, listen, harness the power of team, and approach challenges with passion.

• (00:00) Introducing Mike Maresca, Chief Technology and Transformation Officer at Ulta Beauty
• (01:22) Mike's Career Journey
• (03:08) Modernizing Ulta Beauty's Platform
• (04:47) Ulta Beauty's Customer-Centric Philosophy
• (05:58) Project SOAR and Digital Transformation
• (08:21) AI and Innovation at Ulta Beauty
• (19:07) Sustaining Innovation and Future Plans
• (22:16) Final Thoughts and Advice

Mike Maresca’s career spans technology and digital transformation initiatives, in the retail and consulting sectors. Currently, he is the Chief Technology and Transformation Officer at Ulta Beauty. Previously, he held roles at Walgreens Boots Alliance, serving as Global Chief Technology Officer, and Accenture, where he spent nearly 25 years in various tech leadership positions. He earned a Bachelor of Science and a Master of Science in Aerospace Engineering from Iowa State 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 of Innovation and Digital Enterprise, Patrick and Shelli talk with Michael Ehlers, the new Chief Technology Officer at PlanSource. Mike outlines his leadership philosophy and career evolution, emphasizing that professional growth is rarely linear. He shares formative experiences at Hewitt and Xerox that taught him the importance of transparency during project setbacks, the value of blameless postmortems, and how to treat failure as a chance to grow.

Those experiences inform his current leadership and hiring strategy, which prioritizes candidates with grit, curiosity, and collaborative spirit, over those with rigid technical expertise. He explains that technical skills can be acquired, but behavioral attributes are foundational to a successful dev culture.

Mike shares insights earned through his range of experience, from startups to large multinationals, stressing that at any scale, leaders need empathy to understand customer needs, agility to make change, and transparency to build trust.

• (00:12) Welcome to Michael Ehlers, CTO at PlanSource
• (03:35) Navigating Leadership Challenges
• (10:40) The Importance of Career Growth and Culture
• (23:34) Leveraging Postmortems in Software Engineering
• (28:31) Cultural Shifts in Organizations
• (37:32) Empathy in Innovation: Understanding Customer Needs

Michael Ehlers has had a full career leading software and engineering teams, often at SaaS companies in the HR space. Currently, he is the new Chief Technology Officer at PlanSource. Previously, he has held roles at Benefitfocus, Paylocity, Voya Financial, Aon Hewitt (Alight), and Xerox, where he served as Vice President of Front End Development for their HR Outsourcing business. He earned a Bachelor of Science in Computer Engineering from the Milwaukee School of Engineering.

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.

This is an ‘uncut’ version of the interview. No major edits or audio enhancements have been completed yet. We’re providing this raw version of the interview for review to identify any significant content concerns or edit requests we should take into account when editing and mastering the episode. Tightening up the content (removing silence, umms, and stutters) and cleaning up the overall audio quality will be completed as a standard part of editing and does not need to be specifically called out. 

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.

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 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.

Podcast episode production by Dante32.

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.