Innovation and the Digital Enterprise DragonSpears

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 home
David 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.
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Podcast episode production by Dante32.

Today we're sharing another insightful presentation from our most recent Innovative Executives League Summit, where Leon Chism, the Vice President of Engineering at Evolve, delivered a powerful lesson on collecting critical metrics for organization-wide success. As an experienced technologist and executive, Leon leads teams in unparalleled growth and innovation. In this presentation, Leon dives into how the collection of metrics examining speed and quality paired with human-driven evaluation and consistent reporting are the keys to success. 
In this episode, Leon first dives into DORA metrics and the significance of collecting and reporting those figures of speed and quality. He overviews the additional customization of the data he collects; in one example, he looks closely at aging reports to determine where processes are sticking and gains a live perspective on getting those tasks unstuck by allocating more resources. As the last place to observe metrics, Leon offers a compelling outlook on examining team balance and individual metrics. ("You want to measure the process and not the people.") In further support of optimizing processes and not people, Leon shares his perspective on leaderboards, comparison, and other human-oriented metric frameworks of note. 
In the final segment, Leon answers audience questions ranging from setting WIP limits (never too low), developer satisfaction, and key aspects of the communication around metrics to create a shared understanding and identify the value beyond the data. 
(02:16) – DORA metrics(07:39) – Aging Report(10:15) – Balance and individual metrics(12:22) – Metrics in the boardroom(13:35) – SPACE Framework(15:45) – Manual metric collection(17:19) – Developer satisfaction(18:48) – Gaming the metrics(20:26) – WIP limits(21:45) – Shared metrics and collaboration(26:00) – Hardware, software, firmware(27:05) – Communicating the metrics(28:26) – Value beyond the data
Leon Chism is the Vice President of Engineering at Evolve. As an experienced technologist and executive, he has led innovation and technology at Jellyvision, DialogTech, Rewards Network, Analyte Health, PowerReviews, and ORBITZ. He earned a bachelor’s degree from the Gies College of Business at the University of Illinois Urbana-Campaign.
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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 a...

Today we’re sharing another insightful presentation from our most recent Innovative Executives League Summit, where Maya Mikhailov, Chief Executive Officer and founder of SAVVI AI, discusses machine learning as a powerful toolkit of solutions. Comparing efficiency with and without AI, she highlights how the proper tool makes the difference and cuts through assumptions. Is Chat GPT the AI tool that makes Amazon such a success? No. It is Amazon's recommendation engine built on billions of data points. Looking beyond the hype of select functionalities of machine learning, AI applications abound.
In this episode, Maya introduces AI’s key practical uses, as she currently views the technology: decision automation, classification and prediction, large language models, and writing documentation and code. She emphasizes how natural language makes a query more accessible than programmatic language and shares example after example of increasing efficiency. Maya’s presentation sheds insight into where AI technologies are gaining traction (delinquencies) and continuing to grow in popularity (writing content). 
Maya dives into the importance of guardrails, building trust, and maintaining transparency when utilizing machine learning. She shares where AI is having massive success (summarizing data) and the problems that might emerge from AI reliance (“code bloat”). Maya discusses how when AI is wrong, it is still learning. Employing the right AI tool is essential for strategy and meeting goals.
(1:40) – Machine learning(4:45) – Examining data without AI(5:41) – AI-executed tactics(7:16) – Generative AI(9:14) – Hallucinating (10:57) – The practical realities(12:41) – Decision automation(15:28) – Classifications(17:10) – Predictions(18:15) – Large language models(22:03) – Writing documentation and code
Maya Mikhailov is the Chief Executive Officer and founder of SAVVI AI. She co-founded GPShopper, which Synchrony acquired in 2017. At Synchrony, Maya served as SVP and General Manager of the Direct-to-Consumer group (FinTech AI). She has been a speaker at CES Money 2020 and CTIA and featured in Bloomberg, CNBC, Forbes, Business Insider, and other outlets. Maya served as an adjunct professor at New York University, lecturing on digital and mobile technology. She earned a bachelor's degree in international management at American 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.

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 collaboration
Brad 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.
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