
Innovation and the Digital Enterprise
What does it take to keep your organization growing? Innovation and the Digital Enterprise is a podcast dedicated to providing insights and resources to executives and entrepreneurs focused on 10x growth for themselves and the organizations they lead. We interview leaders from early-stage start-ups to billion-dollar enterprises who have boots on the ground experience to distill their lessons from their victories and their failures.
Learn how these leaders are organizing their teams, establishing a growth-minded culture, and leveraging new technologies such as DevOps and Cloud. Co-hosts Patrick Emmons of DragonSpears, and Shelli Nelson of Madison Industries, chat with guests such as Gene Kim of the DevOps Enterprise Summit, Mik Kersten of TaskTop, and Thomas South of Northern Trust, to uncover tips, tools, and insights gleaned from spearheading innovation initiatives.
Listen Notes
Latest episodes

Sep 8, 2022 • 39min
Highlights from the Innovative Executives League Summit
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. First up, Gale Wilkinson, Founder and Managing Partner of VITALIZE Venture Capital, shares insights on today's trends in angel investing and venture capital. Next, Steve Rubinow, Director of the Institute for Professional Development at DePaul University’s Jarvis College of Computing and Digital Media, speaks to the increasing criticality of continuous learning. Finally, Ateet Adhikari, Chief Operating Officer of ShopRunner, talks about how teams innovate without losing focus.We hope you enjoy these highlights. Be sure to check out the next Summit coming up on November 3rd at the OLC Education & Conference Center in Rosemont IL. You won’t want to miss it, so get your tickets early!If you want to learn more about the Innovative Executives League, the events we host, or any of these innovative leaders, check out our LinkedIn page or visit our website for more information! (01:25) - Angel Investing & Venture Capital Overview with Gale Wilkinson, Founder and Managing Partner of VITALIZE Venture Capital(17:05) - Pre-K to Gray: the Increasing Criticality of Continuous Learning with Steve Rubinow, Director of the Institute for Professional Development at DePaul University’s Jarvis College of Computing and Digital Media(25:34) - Disruption Without Distraction: How to Innovate Without Losing Focus with Ateet Adhikari, Chief Operating Officer of ShopRunnerIf 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 on Apple Podcasts. It really helps others find the show.Podcast episode production by Dante32.

Aug 25, 2022 • 34min
Driving Strategic Change with Patrick Dineen
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. (1:30) – CIO at Nielsen(5:30) – Building relationships across an organization(9:00) – Obsoleting your own role(13:50) – The tyranny of growth(15:15) – Solve bigger problems(19:22) – Thinking weekly(23:40) – Influence, not authority(28:03) – Taking the blame(33:09) – Avoiding “watermelon status”(33:57) – Change managementPatrick Dineen is the Chief Information Officer at Nielsen. Previously, he served in leadership positions at CSG Systems, Harte Hanks, USADATA, Claritas, and Equifax. Patrick earned an MBA from NYU Stern School of Business and a B.S. in Industrial Engineering at Columbia University. 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.

Jul 28, 2022 • 32min
Championing Transparency and Collaboration with Sara Rossio
Not many people are willing to call up their competitors and dive into discussions on bettering the industry at large—choosing to see their competitors as partners. Sara Rossio, Chief Product Officer at G2, is curious about the ways transparency can build trust internally and how to embrace transparency and collaboration with customers, vendors, and across an industry.In this episode, Sara talks about how she approaches product management at G2, including utilizing artificial intelligence and people to moderate and validate reviews and personalizing data to meet a customer’s needs. She discusses her leadership style of providing frequent, direct, and actionable feedback, as well as the importance of supplying context. Sara illuminates the key to her success in product management and how companies can remain competitive: stay curious.(1:05) – Chief Product Officer at G2(4:04) – Transparency(8:19) – Inviting criticism(11:49) – Working with competitors(13:24) – Nokia(16:12) – The customer of tomorrow(17:21) – Biggest challenge: talent(22:27) – Frequent, direct, actionable feedback(25:33) – Tough conversations and a culture of kindness(27:59) – Staying curiousSara Rossio is the Chief Product Officer at G2, a digital marketplace for business software and services that boasts 1.7 million validated product reviews. Sara has worked in project management at PowerReviews, Gogo, Here (a Nokia company), NAVTEQ, and Eaton. She earned a BSBA in Marketing and International Business at Fisher College of Business at the Ohio 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, 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.

Jun 23, 2022 • 32min
Vision and Transformational Change with Mike Kennedy
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.(2:00) – People, process, and technology(4:13) – Recruiting and retaining(6:19) – VSOM(8:50) – The nature of collaboration(9:36) – SaaS solutions(10:48) – “little i” innovation(14:27) – Agile practices(18:08) – Pushing down decision-making(20:46) – Investing in early careers(20:59) – Offering the right incentives(26:34) – Working with veteransMike Kennedy is the Vice President of Technology, Enablement, and Strategy at CDW. He holds an MBA from Gies College of Business at the University of Illinois Urbana-Champaign and has led strategic and business planning at HERE Technologies and The Marketing Store. Mike served in the U.S. Army from 2000 to 2005 after receiving a bachelors degree from the United States Military Academy at West Point. 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.

May 26, 2022 • 32min
Learning to be a Technologist and Executive with Fred Lee
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 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. (1:05) – Amount(5:00) – Adapting to fit the customer(6:52) – Experience across industries(8:55) – Learning through customer proximity(11:01) – Identifying the problems(13:47) – Bringing in talent(17:03) – More process vs. less process(18:52) – Buy now, pay later (BNPL)(20:10) – Building a world-class team(25:51) – Managing a hybrid and remote workforceFred Lee is an experienced engineer and technology executive, currently serving as Chief Technology Officer at Amount. Previously, he served as CTO at Cars.com, Gamut, and Belly , as well as VP of Digital Architecture at Grainger. Fred received a bachelor's degree from Purdue University and a law degree from Loyola University Chicago.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.

May 12, 2022 • 41min
Vulnerability in Leadership with Edward Wagoner
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. (1:25) – Looking ahead at JLL(7:46) – Examining and improving carbon impact(11:19) – Bringing in the best of the best(14:58) – CIO community in Chicago(16:29) – Acceleration from COVID-19(18:16) – Examining the hybrid approach(24:22) – Soliciting feedback(29:48) – Ed’s journey(33:52) – “Do glass-breaking change on yourself”(37:30) – Working with difficult people(39:13) – The power of authenticityEdward Wagoner is the Chief Information Officer at JLL focusing on the intersection of the digital and physical workplace. He has worked in various capacities at JLL over his 26-year career in the company, and he holds a bachelor’s degree from Bob Jones University. In his personal and professional life, Edward operates under the principals of authenticity, vulnerability, and transparency.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.

Apr 7, 2022 • 29min
Rethinking Payment Processing and Fostering Community with Dan Muller
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.(00:31) – The mission of AeroPay(4:02) – Branding with authenticity(5:15) – Chicago’s entrepreneurial ecosystem(7:59) – Recruitment and hiring(10:21) – Specialization(13:28) – Employee endorsements for new hires(15:12) – Growing the business is everyone’s responsibility(16:50) – Money-movement innovation(19:52) – The influence of athletics on leadership(22:13) – Connecting with other founders(24:13) – Tools for getting started(26:00) - 1871 and support communitiesDan Muller is the founder of AeroPay, a patented payments process that enables “smart bank transfers” between business and their customers or other businesses. Prior to AeroPay, Dan held numerous positions at GPShopper, including Vice President of Product and Vice President of Software Engineering. He earned his bachelor’s degree in political science from Franklin & Marshall College.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.

Mar 24, 2022 • 35min
Embracing Failure and Authenticity with Kayne Grau
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.(1:17) Providing critical data with Uptake(4:27) “Crash-course MBA”(6:30) Advice to your early-career self(8:34) Learning through failure(11:20) Accelerated learning(13:29) Being an authentic leader(18:42) Leadership in remote environments(20:30) Keeping employees engaged(22:26) What makes a great visionary?(28:09) No right or wrong path(30:30) Staying open-minded(31:34) Appreciating other rolesKayne Grau is the Chief Executive Officer and Board Director at Uptake, the leader in industrial intelligence software-as-a-service. Before Uptake, Kayne held various senior executive positions at KAR Global, DRIVIN (co-founder and CEO, acquired by KAR Global in 2017), Music Dealers, Apartments.com, Cars.com, and Allstate. Kayne also sits on various advisory boards, mentors local startups, and invests in technology-based companies in Chicago and Dallas.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.

Mar 10, 2022 • 36min
The Entrepreneurial Journey with Jay Rudman
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.(01:17) - What does it look like to trade with Topstep(06:17) - From pro-bono coaching to CEO(09:16) - Business ownership runs in the family(13:40) - Thinking beyond the topline price when selling a business(16:38) - Always ask “How am I going to sell this business?”(21:41) - Self-awareness in leadership(25:22) - Value of humility(29:01) - Two mistakes to avoid when it comes to feedback(31:59) - Seek out mentors early in your careerAs a serial entrepreneur, Jay Rudman has founded/co-founded three companies, each with a successful exit: two sold to publicly traded businesses and one IPO. After his last exit, he joined Topstep - first as a pro bono mentor, then CGO, and ultimately CEO, growing Topstep’s topline revenue ~5x in 5 years, creating double-digit EBITDA, all the while bootstrapping the business (zero investors). Jay has been a finalist for 1871’s “Outstanding Tech CEO Award”, an EIR at Catapult Chicago, a CEO mentor for The Junto Institute, a fractional Biz Dev executive for Jump Capital, and a mentor at Polsky. He earned a bachelor's degree in finance University of Pennsylvania’s Wharton School and an MBA from The University of Chicago Booth School of Business.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.

Feb 24, 2022 • 30min
Building Platforms that Deliver Real Value with Mohan Putcha
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.[01:25] Mohan’s role at AON[02:23] Aon’s five technology markers[05:48] From request to product delivery in 3 months [14:37] Quality database solutions that depend on machine learning [16:39] Digital experience of the workplace[20:52] Biggest challenges in 2022[23:27] Ensuring the right people are at the table[25:38] Value of curiosity and asking questions Mohan Putcha is Vice President, Enterprise Architecture & Technology Strategy at Aon. In this role he leads efforts in enabling sustainable solutions for Aon’s clients and colleagues with a focus on Cloud, DevSecOps, Big Data Analytics, Intelligent Automation (AI/ML/RPA), Digital Workplace and Technology Strategy. Mohan comes to Aon with global experience delivering groundbreaking business results that leverage analytics, cloud, through transformational, enterprise-wide projects in the pharma, medical and risk industries to deliver cloud-based, mobile and highly scalable solutions. 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.