Innovation and the Digital Enterprise

Should we look beyond technology organizations to learn essential lessons on how to innovate and run successful, complex technology organizations? Gene Kim believes so and contains unbridled curiosity for transformation across industries, as seen in his most recent book Wiring the Winning Organization. Gene Kim returns to share new lessons in change-making for leaders and companies tackling an array of challenges. Gene Kim is a bestselling author of several books on technology innovation, DevOps, and organizational strategy. He founded and served as CTO of Tripwire for thirteen years, an enterprise security software company, and is the founder of IT Revolution. Gene offers an engineering perspective with an executive-eye view. In this episode, Gene discusses being inspired by Toyota and his goal to lead great organizations toward the most effective, liberated problem-solving capabilities. He shares how coordination is the layer that is the difference-maker in a successful company and offers several case studies across industries. Gene highlights three key factors in a cohesive organization: 1) independence of action, 2) time (for practice and planning, and experimentation and implementation), and 3) actionable feedback that reaches the right people at the right time. Gene offers a metaphor from his book—moving a couch—that exemplifies his experience in communication and coordination. With this simple metaphor, Gene shares how small, cross-functional teams with the right number of collaborators are a great tool for success.  Join Gene in Las Vegas from August 20 to 22, 2024, at the Enterprise Technology Leadership Summit (formerly DevOps Enterprise Summit). (01:40) – Gene Kim returns(04:22) – Layer three as difference-maker(09:22) – Healthcare case studies(11:55) – Three mechanisms for a cohesion(15:04) – The CheckBox Project(20:29) – “Slowification”(26:55) – “Great in the large, great in the small”(29:03) – Specialization of roles and coordination(34:34) – The technology leader’s bossGene Kim is an author, researcher, and technology leader studying high-performing technology organizations since 1999. Gene founded and served as Chief Technology Officer of Tripwire, Inc. for thirteen years, an enterprise security software company. He is the WSJ bestselling author of Wiring the Winning Organization, The Unicorn Project, and co-author of The Phoenix Project, The DevOps Handbook, and the Shingo Publication Award-winning Accelerate. Since 2014, he has organized the Enterprise Technology Leadership Summit (formerly DevOps Enterprise Summit), studying the technology transformations of large, complex 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.

We had a great conversation with David Heinemeier Hansson in 2023 and are excited to reshare it in our “Best Of” series.Originally published 11/2/23.Profound innovation has occurred across web-based communication technologies in the last decade, and truly accelerated in the years since the start of the pandemic. But David Heinemeier Hansson recognized a massively neglected arena, one we all use, every day: email. Bringing his experience as co-owner and Chief Technology Officer at 37signals (Basecamp, Ruby on Rails, and more), David launched HEY, an innovative approach to email that provides a modernized, user-first service. In this episode of Innovation and the Digital Enterprise, David articulates a dedication to forging new paths in software and entrepreneurship.He shares important lessons in approaching remote work, including the essential pillar of embracing asynchronicity. He dives into how he structures his day for success and offers a counterpoint to the American workplace culture of bragging about busyness and 80+ hour weeks. Finally, David provides insight into the current state of cloud technology and his company’s recent—successful and swift—migration off the cloud. (01:48) – 37signals(03:27) – HEY(09:54) – Advantages(17:32) – Detecting spy pixels(19:45) – The pandemic’s impact(23:42) – Embracing asynchronicity for success(29:07) – An American culture of busyness(34:31) – Importance of sleep(38:52) – Cloud technology(46:55) – Bringing applications homeDavid Heinemeier Hansson is co-owner and Chief Technology Officer of 37signals (Basecamp & HEY), creator of Ruby on Rails, and best-selling author, including REWORK, It Doesn’t Have to be Crazy at Work, and Remote: Office Not Required. David is a Le Mans class-winning racing driver, photographer, antitrust advocate, and investor.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.

Experienced technologist Leon Chism discusses the importance of collecting metrics for organization-wide success, focusing on DORA metrics, process optimization, and team balance. He emphasizes measuring processes, not people, and sharing a holistic interpretation of data with leaders for effective decision-making.

Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit, where Tanya Hannah discusses the roadmap to navigate the ever-evolving tech landscape. As a seasoned transformational business executive, Tanya offers the pillars needed to survive major shifts and thrive in the opportunities presented by them. In this episode, Tanya shares how critical a shared vision and strategy is in preparation. Teams cannot operate only with yesterday’s logic; they must look forward in anticipation of a pivot. Tanya offers how technologists can operate at the key intersection of short-term performance and long-term planning. She stresses the importance of a business perspective having a place in tech conversations and leaning into a skillset that embraces both.As an award-winning technology leader, Tanya sees a path forward that focuses on data, talent, and vision. Tanya describes how data provides the competitive advantage businesses are looking for and how the ability to manipulate and understand the data is essential for the entire team. In focusing on the team itself, Tanya addresses how people are the key factor in remaining nimble (embracing in-house talent) and how the current shift in the labor environment points to the direction companies must anticipate. As remote and hybrid work continue, Tanya dives further into how focusing on talent is not only essential but teams and individuals must have a common understanding of the shared vision and strategy for success. While acknowledging the evolving technology and the often disruptive forces that shape the world today, Tanya Hannah offers a foundation to prepare for the future with tech and talent. (01:17) – A room of disruptors(02:36) – Adaptation(04:33) – Acting with yesterday’s logic(08:40) – Preparing to pivot(10:35) – Driving business with tech(13:02) – The win-win(14:26) – Understanding data is a must(16:10) – Focusing on people(21:55) – How are we planning?Tanya Hannah has held executive and senior roles at Aon, Amazon, CSC, and King County, Washington. Tanya is a three-time CIO 100 Award winner and a 2021 National CIO of the Year. She’s a graduate of the University of Maryland.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.

Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit, where Desiree Vargas Wrigley, Chief Innovation Officer of P33 Chicago and Executive Director of TechRise by P33, delivered a lesson in stakeholder-centric design. Desiree overviews the challenges Chicago’s underrepresented tech founders face and the process of developing TechRise’s initiatives. Highlighting the impact of TechRise and P33, Desiree presents a galvanizing picture of Chicago-based innovation that utilizes local money to generate a cycle of loyalty, growth, and investment that leans into Chicago’s advantages. In this episode, Desiree asks: “Who succeeds when you succeed?” As an enthusiastic believer in Chicago’s potential as an innovation hub, Desiree is also unafraid to point out its shortcomings, such as the lack of popularity in social ventures and lack of recycled capital. Demonstrating a stakeholder-centric design process with the case study of TechRise, Desiree shows how focusing on the key question of identifying all the stakeholders and all the solutions that benefit them drives success. She discusses sifting through bias for actual data and the extensive discovery process that went into developing the initiatives of TechRise. Desiree articulates how re-imagining pitch competitions (frequency, environment, etc.) has opened doors for founders by acknowledging the obstacles that women founders and founders of color often face. Desiree shares her interest in conscious capitalism and asks, “What else is possible?”(1:15) – P33 Chicago(3:42) – Thinking about success(4:53) – A foundation for providing support and resources(6:57) – Stakeholder-centric design in four steps(9:36) – Funding women and founders of color(12:49) – TechRise(15:20) – Identifying solutions(16:35) – Weekly pitching(19:12) – Looking at impact(21:16) – What else is possible?Desiree Vargas Wrigley is a serial entrepreneur with a track record of empowering women and people of color in the world of investing. Desiree is the Chief Innovation Officer of P33 Chicago and Executive Director of TechRise. She is a founding partner of The Josephine Collective and previously co-founded GiveForward. Desiree earned a bachelor’s degree in Latin American Studies from Yale 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.

Maya Mikhailov, CEO of SAVVI AI, delves into practical AI applications beyond the hype, emphasizing decision automation, classification, and prediction. She discusses the importance of natural language in querying data and the need for guardrails and transparency. Maya highlights AI successes in summarizing data and warns of potential issues like 'code bloat'.

Coupling a charitable mindset and a drive to solve some of the toughest intellectual and scientific problems has led to success for P33 Chicago and founding Chief Executive Officer Brad Henderson. Serving Chicago and embracing the city’s challenges and strengths, Brad envisions the city as a hub for new technologies built on collaborative and dynamic innovation, all while embracing inclusive growth.In this episode, Brad shares the successes of P33 Chicago and TechRise’s efforts, including outlining how two million dollars invested into Black, Hispanic, and women founders led to ninety-three million in additional private financing. He discusses the lasting effects of starting a business under-capitalized and the realities of how most founders raise capital. Brad offers insight into connecting investors with opportunities where they might lack first-hand expertise or experience and the benefits of encountering and working with new people and ideas.Brad dives into ongoing success stories in Chicago (EventNoire and more), the ripe environment for a Chicago-based battery boom, the new CZ Biohub, and the aims and recent triumphs of Innovate Illinois. He shares a key component to the city's success: the collaborative spirit of the top-caliber universities. Brad paints a picture of an innovative Chicago that utilizes the abundance of college graduates and embraces scientists and thinkers across institutions working together to create new technologies funded by bold Chicago investors and building on the city’s history of innovation.(04:26) – Introducing Brad Henderson and P33 Chicago(05:52) – TechRise(07:27) – The impact of an under-capitalized start(09:45) – Proof points and coaching founders(12:05) – Success story: EventNoire(14:21) – A battery boom(18:41) – Chicago-based investors(20:34) – The impact of exceptional, collaborative universities (25:25) – Where is Chicago headed?(26:17) – Leveraging a small staff(29:38) – Chicago-based innovation and collaborationBrad Henderson is the Founding Chief Executive Officer at P33 Chicago, the forward-thinking nonprofit organization dedicated to elevating Chicago's status as a world premier hub of technological discovery and development. Brad's leadership extends to various roles on boards and advisory committees of Interfaith Youth Core (Board Chair), the College Visiting Committee at the University of Chicago, the President’s Advisory Council at the University of Illinois, the College of Computing Advisory Board at Illinois Tech, Rush University Medical Center, Rush University (Board of Governors), Chicago Council on Global Affairs, and the Chicago History Museum. Brad earned a bachelor’s degree in economics with honors and a master's in social science from the University of Chicago. A Rhodes Scholar, Brad also earned a master’s of science in economics and social history from the University of Oxford and an MBA from Saiid Business School at the University of Oxford.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.

Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit, where Michelangelo D’Agostino, VP of Machine Learning at Tegus, delivered a foundational lesson about large language models. Imagine you are Rip Van Winkle, as Michelangelo puts it, and you have woken up after a long sleep and encountered the current AI landscape. What have you missed? What do you need to know to move forward? Calling upon his data analysis and machine learning expertise, Michelangelo offers clear, concise insights to introduce audiences to the capabilities and shortcomings of large language models today.  In this presentation, Michelangelo integrates large language models to demonstrate their abilities. Defining the term and other critical ones (What does GPT mean?), he dives into the factors that have led to the exponential growth in these models since 2020 and details the training methodologies that led to major advances. Michelangelo covers how instruction tuning brought an exercise in probability to usefulness that will change industries.Offering insight into the challenges large language models are encountering, Michelangelo walks audiences through a “hallucination,” where the LLM offers a confident answer that is incorrect—a concerning flaw--and displays how prompt engineering generates the correct result with a minor tweak. With the input and output being natural language, Michelangelo encourages people to embrace the low barrier of entry to try out the models directly (OpenAI’s ChatGPT, Anthropic’s Claude, and Google’s Bard) by writing prompts and learning its capabilities firsthand. Michelangelo shares the areas where he’s excited about the potential of large language models and their transformative power for text-heavy industries. (00:58) – Demystifying AI(03:37) – Large language models(05:13) – Unpacking training(08:43) – Why now?(12:05) – Increased potential(14:50) – Hallucinations(16:26) – Prompt engineering(18:25) – Applications of language models(22:48) – Play around with it!Michelangelo D’Agostino is the Vice President of Machine Learning at Tegus. Previously, he held leadership roles in data and machine learning at Cameo and ShopRunner. Michelangelo’s career as a technologist career is marked by his exploration of large language models and their applications in financial text data. He studied physics, earning a bachelor’s degree from Harvard University and a Ph.D. from the University of California, Berkeley.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.

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. (02:12) – Introducing Chris Brown(04:44) – CPO vs. CEO(06:18) – Sales in the SaaS world(08:51) – Relativity(10:46) – Building an effective SaaS company(15:29) – Co-innovating with customers(17:51) – AI and the law industry(22:09) – Looking ahead(23:48) – An acquisitive approachChris 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.

Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit, where Mark Achler, Managing Director of MATH Venture Partners, spoke about the central role of trust in a successful company—with customers, employees, and partners. In this presentation, Mark details three experiences involving broken trust. He shares his journey remaining optimistic in the face of negativity and an array of reasons to embrace cynicism. Mark touches on several occurrences in which trust, ethics, and standards have been at the center of faltering companies and outlines why trusted companies perform better. (01:11) – Three stories and a question(20:34) – Optimism and cynicism(25:22) – Economics of trust(30:50) – Loss of trust and manipulation(37:37) – Trust as offense and defense(39:25) – Breaking promisesMark Achler is the Managing Director at MATH Venture Partners, a VC fund focused 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.