Innovation and the Digital Enterprise

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.

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.

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.

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. (01:08) - i.c.stars mission(07:00) - Resiliency in candidates(09:19) - Untapped talent(14:19) - Chicago tech culture(20:42) - High Tea(26:56) - Program breakdownSandee Kastrul is president and co-founder of i.c.stars, an innovative nonprofit leadership and technology training program founded in 1999 to prepare inner-city adults for technology careers and community leadership.Prior to i.c.stars, Sandee’s experience as an educator, diversity trainer, educational consultant and a performing artist drew her creative talents to the forefront. Her accomplishments include designing a comprehensive science and civics interactive program for GED students at Jobs for Youth, implementing a professional development program with Harold Washington College Career Center, developing experiential learning modules for over 70 schools and creating artist in residency programs as well as training artists to work in classrooms for arts organizations.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.

Rand McNally’s Chief Technology Officer, Steve Caudill joins Pat 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. (01:13) - Technical product development(03:17) - Recruiting product makers(05:46) - Seek out diverse perspectives (08:35) - Pair programming during interviews(10:19) - Addressing salary expectations(12:38) - Making products that have impact(17:18) - Challenging remote work trends(19:15) - Taking ownership of what you make(22:03) - Buy-in from the business side(28:16) - Find the shortest path to money(30:16) - Leveraging brand trust(32:57) - Benefits of mentorshipTrucks, tractors, maps, connected devices, oil and gas, potato chips, silicon chips, educational devices and more have been part of a nearly 40-year career for Steve Caudill, the Chief Technology Officer at Rand McNally. Before joining Rand McNally, Steve was a director at CNH industrial, where he was responsible for delivering the farm operations and fleet management components of CNH Industrial’s connected offerings. Steve is the author of A Hero Behind Every Tree: The Non-Technical Reasons Your IT Investments Fail. He received a BA in Computer Science from the University of Maryland and an MBA from the Naveen Jindal School of Management at University of Texas 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.

What does change management look like in a world of constant, rapid change? Allen Smith, CIO at Baker Tilly, believes keeping up with the pace of change today requires rethinking change management as a discipline, including the rigid processes and communication protocols from traditional waterfall development.Allen joins Patrick and Shelli to talk about the increasing overlap between our personal and professional lives. People bring the expectations they have for consumer software into their view of workplace software and tools. Whether they like it or not, businesses have to contend with any negative aspects of that trend. Why not lean into the change and capitalize on the advantages?(01:19) - What makes Baker Tilly different?(02:45) - Ability to change(04:59) - Agile development(07:44) - Part of a progression(11:41) - Adoption rate(16:09) - Building a long-term strategy(22:17) - Digital nomads(23:44) - Candor in mentorshipAllen Smith is the Chief Information Officer of Baker Tilly US, the 9th largest accounting firm with $1b in revenue. Allen has served as the firm’s CIO for nearly 20 years and leads all technology strategy and execution across the firm. Under his technology leadership, Baker Tilly has grown its revenue more than 1000 percent. During this growth, Allen has established a strong track record of results by creating and fostering a culture driven by collaboration and camaraderie among his team. This open atmosphere has created team cohesion, produced above average retention and driven results that are well known within the industry. In addition to his executive leadership role with Baker Tilly, Allen serves in senior leadership roles for Baker Tilly International. These roles include Chair of the North America IT Committee and Co- Chair of the Global IT Committee. Allen also served for four years as a Board Member of the Information Technology Alliance (ITA), including holding the roles of Vice-Chair and Chair of the Board during his tenure. He works directly with the AICPA in a volunteer role and has spoken at numerous domestic and international industry, technology and human resources conferences. Prior to joining Baker Tilly, Allen served in senior leadership and technology roles in a variety of organizations, including technology start-ups, hyper-growth enterprises and outsource service providers. His industry experience includes accounting, legal, financial services and real estate. Allen understands the importance of unwinding. He enjoys golf, traveling and curling. A small claim to fame is that Allen was an on-ice official for the 2006 Olympic Team Trials for Curling. While he is passionate about curling, he is the first to state his officiating skills are better than his curling skills.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.

At TransUnion, creating innovative products, building talent, and delivering excellent customer experiences start with an environment where trust is possible. Swati Shah, U.S. Markets CIO, talks with Patrick and Shelli this week about what cultivating that trust looks like for the organization. She also describes the various programs in place to support continuous learning for cross-functional teams and the importance of helping engineers understand the ‘why’ in addition to the ‘what’ for the solutions they are building. (01:24) - Swati’s role at Transunion(02:57) - Delivering Value to customers(04:40) - B2B2C(06:47) - Understanding your customer's customer(09:14) - It’s about the people(12:38) - Building talent(17:23) - Trust within the organization(20:05) - A philosophy of life-long learning(22:33) - Resiliency & grit(25:33) - Seeking mentorshipSwati Shah is Senior Vice President and Chief Information Officer at TransUnion for US Markets where she is responsible for all technology and delivery within the US Market. Prior to TransUnion, Swati served as Senior Vice President of Emerging Technologies at US Bank. There she was responsible for leading the enterprise API and microservices strategy, bringing business and technology together to produce API-as-a-Product. She also led the DevOps strategy to drive business agility, cloud adoption and modernization. Swati has also held leadership positions at CapitalOne, Thomson Reuters, and Motorola. Swati holds a Bachelor of Science degree in Mathematics, a Master's of Science degree in Computer Science, and an MBA from Lake Forest School of Management in 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.

Experiencing a sudden 90% revenue drop is a formidable challenge for any business. When SpotHero found themselves there at the start of the pandemic, the team took it as an opportunity to pause and rethink their business. In this episode Matt DiBari, Chief Product Officer at SpotHero, talks with Patrick and Shelli about how creative thinking and a strong team foundation allowed SpotHero to weather the sudden downturn. He also discusses how a culture of looking around corners and reacting with wonder fuels innovation both today and for the company’s ‘horizon 3’ plans. (04:19) - COVID’s influence on parking trends(08:06) - Weathering a 90% revenue downturn(13:09) - Transparency to countering uncertainty(16:17) - Looking around corners to maintain an edge(23:17) - Remember to react with wonder(25:21) - Fostering cross-team learning(28:38) - Curiosity and humility as keys to leadershipMatt DiBari (he/him/his) is Chief Product Officer at SpotHero. He joined SpotHero in 2019 as VP of Product, bringing more than 15 years of experience to the role. At SpotHero, Matt is primarily responsible for product vision and strategy, bringing together his love of product innovation and more than a decade of automotive experience. Prior to SpotHero, Matt was the Senior Director of Product Management at Cars.com, after having honed his automotive expertise at CDK Global. Matt has a BA in computer science, math, and philosophy from Augustana College and an MS-MIS and MBA from the University of Illinois at 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.

While eye-popping capital rounds make headlines, sometimes smaller is better when it comes to venture fundraising. Will McGivern-Smith, Chief Strategy Officer of TrueData joined Patrick and Shelli to discuss what questions to answer for your business when considering venture capital. Understanding the type of company you’re building, the problem you’re solving and the total addressable market is a good place to start. Listen in to get Will’s take on what factors to weigh when looking for the best fundraising partner, how to nail your pitch by keeping it simple, and what motivates different types of investors(01:13) - Will’s origins(08:02) - TrueData’s start(11:18) - The pros and cons of venture capital(14:39) - Smaller versus larger funds(19:59) - Series A, B, and C funding(28:08) - Investor focal points(30:14) - K.I.S.S.(33:29) - Finding the right network of people(36:21) - Being vulnerable with mentorsWill McGivern-Smith is the Chief Strategy Officer of TrueData and brings an emphasis on desktop and mobile activation, optimization, and analytics. Prior to joining TrueData, Will worked at Nielsen Catalina Solutions for five years, shaping and growing a diverse set of functions including Data Science, Product, Business Development and Sales. Will holds a BA in Economics from Carleton College, and an MS in Predictive Analytics/Data Science from Northwestern 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.

Timothy Alvis is the Chief Product Officer at SPINS and has over 20 years of experience marrying product, consumer needs, and business outcomes. He joined the podcast today to offer his tips for product teams and why they should focus on understanding problems rather than coming up with solutions. Having started his career as the founder of multiple gaming companies, Tim also discusses the creativity involved with popular video games like Minecraft and Roblox. Tune in for his insights.(01:18) - Providing shaped retail insights(03:51) - The eras of the gaming industry(10:07) - Practicing team dynamics(16:47) - Bad/lucky vs. good/unlucky(20:42) - How to get truthful feedback(25:15) - Finding the “why” in product leadership(30:35) - Being problem-focused(37:00) - Driving toward your destination(38:23) - Shifting mentorsTimothy Alvis is the EVP of Product Innovation at SPINS, a leading provider of retail, consumer insights, and analytics for the natural, organic and specialty products industry. As EVP of Product Innovation. He is responsible for the technology and product strategy and leads the data governance, engineering, product management, product design, and development operations team.Before becoming the EVP of Product Innovation. Tim held numerous other positions at SPINS, including president of retail operations and vice-president of product. Prior to SPINS, Timothy held positions at Microsoft, Right Point, and Amazon. He launched his first software startup at the age of 20 and has co-founded another five companies.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.