Innovation and the Digital Enterprise

When Tommy Richardson enlisted in the United States Army at 18, he narrowed his options to operating a tank or going into computer operations and programming. In selecting the latter, he launched a lasting career in the field, has led several major companies in C-suite positions, and recently arrived as Chief Product and Technology Officer for Litmos, leading product innovation. In this episode, Tommy discusses balancing technology evolution to remain competitive, feature development to meet customer demand, and product innovation to keep ahead of the curve. He shares insight into establishing the right resource allocation for the various product development workstreams, including security, tech debt, enhancements, defects, and support. Tommy also dives into lessons learned from his time at startups and in private equity, as well as what’s ahead for Litmos this year. (01:01) – Product at Litmos(04:21) – Training in a rapidly changing world(06:29) – Feature-richness as a differentiator(08:23) – Individualized content(10:10) – Technology innovation and prioritization(18:57) – The journey and the destination(21:13) – Learning from startups(23:35) – The world of private equity(24:57) – Major influencesTommy Richardson is the Chief Product and Technology Officer at Litmos with over twenty-two years of experience across industries. He’s held executive leadership roles at FinThrive, BARBRI Global, Vector Solutions, Nextech Systems, Teradata, Siemens Healthineers, ADP, and more. Introduced to computer programming in the United States Army, Tommy studied at Auburn University in Montgomery and earned an MBA from The University of Georgia.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.

Between confidentiality agreements, polite manners, and ego, it can be difficult to get a real story of what selling a company is like. Breaking that taboo was the inspiration for Exit Right, a book co-authored by today’s guest Mark Achler, Managing Director at MATH Venture Partners.  In this episode, Mark shares the hard-earned lessons captured in Exit Right about key actions that lead to successful exits. He makes the case for viewing these transactions not as a moment in time but as an opportunity to build relationships and value over a long time horizon. Mark emphasizes the need to deeply understand the rationale for the transaction, the value of maintaining empathy for all stakeholders, and why trust is everything.(01:36) – MATH Venture Partners(04:23) – Exit Right: how to sell your startup(10:29) – FAIR framework for successful acquisitions(18:53) – Start early & build relationships(21:03) – Mark’s empathy rules(25:40) – Upcoming debt apocalypse(28:52) – Are economic interests aligned?(31:25) – The inevitable economics of trust(39:00) – Widening your lens beyond a single dealMark Achler is the Managing Director at MATH Venture Partners, an early to growth-stage venture capital fund focusing on technical and digital companies. Mark is a faculty member at Northwestern University Kellogg School of Management in entrepreneurship and innovation and co-authored Exit Right with Mert Iseri. He earned a bachelor’s degree in history and economics from 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, 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.

One consequence of success for a startup is outgrowing the very strategies that made you successful. As an experienced founder, it’s a challenge Justin McNally was prepared to tackle as Chowly grew from a seedling idea to a market leader in point-of-sale integration. At each stage of growth, Justin’s role, and sometimes title, evolved to meet the changing needs of the organization. Through the lens of his current role as Chief Innovation Officer, Justin discusses traversing the gap from startup to established company, shifting hiring emphasis from generalists to specialists, and adapting competitive strategies as a market matures. He also offers perspective on avoiding stagnation and continuing to innovate even as the risk calculations change with scale.  (01:07) - Starting Chowly (05:16) - Growing up with entrepreneurship(12:33) - Defining your moat(16:55) - How risk tolerance changes with growth (19:06) - Checking your ego at the door as a founder(21:52) - Role of the Chief Innovation Officer(24:35) - What’s ahead for Chowly and the industry Currently, Justin McNally is the Chief Innovation Officer at Chowly, a direct POS integration for third-party delivery platforms. Justin is an experienced founder with a demonstrated history of working in the marketing and advertising industry. He graduated with a BLA focused on Interactive Arts & Media from Columbia College Chicago. Some of his skills include Digital Strategy, PHP, WordPress, Ruby on Rails, and Content Management Systems.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.

The Innovative Executives League recently held its second in-person summit with an amazing slate of thought leaders sharing their experiences and perspective on innovation and leadership. In this episode, Patrick and Shelli highlight a variety of insightful presentations from the event. If you're unfamiliar with the Innovative Executives Leagues, it's an invite-only community of innovators, entrepreneurs, and intrapreneurs with a growth mindset and a passion for innovation. It was founded to increase the network of innovation in the Chicagoland area and also on a national scale. If you're interested in becoming a member, send us a message at LinkedIn or visit our website at www.dragonspears.com/innovative-executives-league.(01:11) - Developer Experience: Improving Business Performance by Focusing on Your People with Deepika Duggirala, SVP, Global Technology Platforms at TransUnion(07:38) - Creating an Effective Innovation Culture with Jack T. King, CIO at AAOS(13:56) - Bridging the Employee Experience Gap in a Digital World with Kuldip Mohanty, CIO HUB International(19:45) -  Finding Value in Machine Learning, a 5-Step Framework with Maya Mikhailov, Founder of SAVVI AI(28:49) - Corporate Social Innovation with Adam J. Hecktman, Founder of For Good Advisory and Former Dir. of Global Workforce Ecosystems, Microsoft Philanthropy(34:12) - The Ambidextrous Organization with Mike Kennedy, VP Technology Enablement and Strategy at CDWIf 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.

A great teacher can be the key to welcoming challenges, self-confidence, and a curious spirit. In the case of Larry Berlin, Chief Financial Officer at Freedom Fries, great teachers also inspired a lifelong commitment to mentorship, including his critical mentor role for the New Venture Challenge, an accelerator program that has launched Grubhub, Braintree/Venmo, and many more successful companies.In this episode, Larry shares details of the development process and aims of his recent venture: search engine and news aggregator Freespoke.com. He outlines how to approach analyzing product-market fit and your company’s competitive grid. Bringing lessons from his experiences mentoring an array of startups, Larry discusses how to deal with surprises and highlights the “need-to-know” aspects of a pitch.   (01:13) – Freespoke.com(05:21) – The challenges of managing a startup(11:24) – Flexibility as an entrepreneur(14:21) – Product-market fit and building your competitive grid(21:31) – Encountering surprises(24:12) – Testing your assumptions(29:52) – New Venture Challenge(34:24) - MentorshipLarry Berlin is the CFO of Freedom Fries (Freespoke.com), a mentor at the University of Chicago Booth School of Business, and leads Blue Point Advisory Services. Previously, he worked at First Analysis for nineteen years and earned 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.

Specific, problem-solving artificial intelligence is here, but when will the general, exponentially learning AI arrive in full force? Technologist Michael Housman, CTO of a stealth project at Doma, shares the anticipated arrival of AGI and his career contributing to machine learning and artificial intelligence. In this episode, Michael debunks misconceptions about AI and illuminates how malicious actors have benefitted from developments in data science (and how we can use data to catch them). Beginning his impressive career with a Ph.D. in economics, Michael shares insight into matching your strengths to the right company culture and how to know when you've achieved product-market fit.(1:08) – Economist to engineering team lead(3:02) – Singularity University(4:29) – Misconceptions about artificial intelligence(12:19) – Technology to enable general AI(14:19) – Catching bad guys with data(21:31) – Innovation and globalization(25:46) – Big companies acting like a VC fund(29:34) – Product-market fit(34:40) – Company-employee matchMichael Housman is a technologist with over ten years of experience leading engineering and data science teams and architecting artificial intelligence platforms. Michael is the CTO of a stealth project at Doma, a faculty member at Singularity University, and has held several executive roles, including at Evolv and RapportBoost.AI. He earned a Ph.D. in Applied Economics & Managerial Science at The Wharton School and a bachelor’s degree in health care policy at Harvard 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.

Adaptability is an essential skill for anyone navigating their career in a company experiencing growth. Chief Information Officer James Gray curates his teams with this priority due to REEF’s exponential growth in recent years, especially as the neighborhood-focused company saw the desire for the proximity of goods and services increase during the COVID-19 pandemic.In this episode, James Gray shares insight into the importance of articulating your needs as an employee, addressing company-employee value mismatch, and managing vertical and horizontal growth. James discusses REEF innovations, like “ghost kitchens,” and the opportunities for those interested in working with the mobile, modular, and smart company. (1:31) – What is REEF?(3:22) – Ghost kitchens(6:20) – Growing REEF(11:26) – An entrepreneurial company(15:40) – Acceleration from the COVID-19 pandemic(17:12) – Curating a team in a growth company(20:40) – Addressing company-employee mismatch(25:25) – The biggest surprise of the past year(26:48) – Mitigating inflation and product capabilityJames Gray is the Chief Information Officer of REEF. His expertise in data, product management, artificial intelligence, IT operations, software engineering, and sales has led to high-level roles at Microsoft, Aspen Technology, and Chevron. He hosts the podcast Career Strategy Coach. James earned an MBA from the Haas School of Business at the University of California Berkeley, a master's degree in information and data science from the School of Information at UC Berkeley, and a bachelor's degree in electrical engineering from Union 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.

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 developed at MIT and Northwestern to drive her career progression through positions in operations, planning, project management, sales, and now, artificial intelligence and machine learning. In this conversation with Pat and Shelli, Deborah also discusses her contributions to the innovative processes at Apple and NAVTEQ and how she navigated her career when opportunities did not automatically appear. (1:27) – Machine learning and AI(8:09) – Studying material science(11:38) – Journey to NAVTEQ(18:14) – Taking on different roles(21:45) – Working with an executive coach(26:51) – The engineering of sales(28:33) – Approach to leadership(30:27) – Advocates in your networkDeborah Spence-Cummings is the Director of AI/ML Operations at Apple. She has previously held executive and senior roles at HERE Technologies and NAVTEQ across operations, planning, program management, and sales. Deborah earned a bachelor's and master's degree in materials science and engineering at the Massachusetts Institute of Technology and an MBA at the Kellogg Graduate School of Management at 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.

With a decorated thirty-year career in the U.S. Army behind him, General James Mukoyama’s retirement is one of passionate advocacy and aid for veterans. In the organizations he leads, Military Outreach USA and Enabled Enterprises, as well as other faith-based acts of service, General Mukoyama believes in leading by example and with care while maintaining balance in your life. In this episode, General Mukoyama highlights two critical efforts of Military Outreach USA: reducing veteran suicide rates and equipping veterans exiting homelessness with much-needed supplies. He outlines how the organization approaches its work and provides a crucial explanation of "moral injury." General Mukoyama shares advice on leadership across industries, including four essential pillars of fitness and the importance of communicating expectations.(01:46) – Military Outreach USA(18:14) – Growing up Japanese-American in Chicago(25:38) – Journey to Major General(28:00) – Surviving Agent Orange(33:03) – Methods in leadership(39:10) – Testifying before Congress(43:14) – Caring for your subordinates(44:44) – Maintaining a healthy balance(48:29) – “Coming Home” Veterans Retreats(50:03) – Get involvedMajor General James H. Mukoyama, Jr. is the President and Executive Director of Military Outreach USA, Partner and Director at Enabled Enterprises, and served in the U.S. Army from 1964-1995. In 1989, he became the first Asian-American in the history of the United States to command an army. He earned a bachelor’s degree in English Literature and a master’s degree in the teaching of social studies at the University of Illinois.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.

Imagine a career sparked from the desire to play a video game that’s out of your budget. Marc Saltzman began his career as a journalist and technologist with a promise of publishing a review. With twenty-five years in the industry, Marc shares insight into automation and electrification alongside the questions these current innovations prompt in consumers and businesses alike.In this episode, Marc highlights several moments for the industry: the misdirection of Blackberry and Motorola, Queen Elizabeth’s pioneering use of technology, and the current advances toward autonomous and electric vehicles. He provides insight into the integral role of human touch in the ever-evolving supply chain and how this growth may impact employment. (1:17) – “Geek speak to street speak”(4:52) – The fall of Blackberry and Motorola(8:16) – Queen Elizabeth’s embrace of technology(13:51) – EVs(21:11) – Automation(29:39) – Humans in the supply chain(37:57) – Becoming a technologistMarc Saltzman is a technology evangelist, journalist, television, radio, and podcast host, producer, and author with twenty-five years of industry experience. Marc is a contributor to more than twenty prominent publications, including USA Today/Gannett, AARP, MSN, and more. He has authored over a dozen books and has appeared as a technology expert and commentator on television stations around the world. Marc hosts Tech Impact on Bloomberg Television and Tech It Out via Radio America.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.