By Barry O'Reilly
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The podcast currently has 140 episodes available.
Driving innovation in technology and business transformation demands visionary leadership, seamless integration of business and tech strategies, and a willingness to take risks. Today's guest, David Gledhill, exemplifies these qualities as he shares his experience leading DBS Bank through a remarkable digital transformation and beyond.
David Gledhill is a seasoned technologist and business leader. As the former Group Chief Information Officer at DBS Bank for over 11 years, he spearheaded the bank’s technology and transformation efforts, building a high-performance culture and integrating technology into the core of the business strategy. Under his leadership, DBS achieved global recognition for its digital transformation, and David’s journey has been featured in Harvard Business Review as one of the top global transformations. After his time at DBS, David held a senior role at Lloyds Banking Group, further enhancing his expertise in large-scale transformation. He is now a non-executive director at companies like Singapore Airlines and serves as a senior advisor to McKinsey & Company.
In this episode, host Barry O'Reilly invites David to discuss his leadership journey, from reshaping the technology at DBS to embracing a digital-first strategy. David offers insights on making tough decisions, aligning business with technology, and leading organizations through massive change.
Key Takeaways:]
Barry introduces David Gledhill, highlighting his role as former Group CIO of DBS Bank and his contributions to the company’s digital transformation.
"I started off even when I was 11 or 12, building stuff with electronics and did computing electronics at university."
"When my career progressed, I became more of an exec... And then back in 2008, an opportunity came to join DBS Bank and become a CIO again, and get really back into tech."
"They’d spent like $300 million of a $200 million budget. And the estimate was this is going to take another five years and another billion dollars to complete."
"I had to basically scrap that whole program and restart... it was a total reset of strategy, roadmap, people, everything from scratch."
"We came up with this what we call the buy, sell, hold diagram... I love the system, and do more with it. Sell it to get rid of it. Hold is kind of meh but it'll keep going for now."
"We created a ‘two in a box’ leadership model, where a business leader and a tech leader had joint KPIs... business KPIs, customer service levels, tech modernization – everything."
"We looked at Google, Amazon, Netflix, Apple, LinkedIn, Facebook, and I came up with this idea of what if we were the D in Gandalf?"
"It’s hugely satisfying when you see that happen... they’re doing some super risky things, which may or may not play out, but that’s great fun to be part of."
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Leadership in technology and operations requires a strategic focus on scaling businesses, empowering teams, and driving innovation. Today's guest, Richard Lennox, exemplifies these qualities as he shares his journey from leading Skyscanner through rapid growth to scaling healthcare innovation at Current Health.
Richard Lennox is an experienced technologist and business leader. As Senior Director at Skyscanner, he led the company’s engineering and operations teams through a pivotal period of scaling, focusing on high-performance teams and continuous delivery. After Skyscanner’s successful exit, Richard transitioned to COO at Current Health, where he helped scale the business, focusing on home healthcare delivery through technology. His leadership experience spans multiple industries, making him a valuable mentor and guide for those navigating startup growth and innovation.
In this episode, host Barry O'Reilly invites Richard to discuss his journey, from his early days at Skyscanner to his role at Current Health. Richard provides insights into scaling startups, the importance of data-driven decision-making, and the operational challenges of growing high-performance teams.
Key Takeaways:
Additional Insights:
Episode Highlights:
"I got really lucky early on in my career, joining an early startup, which shaped my thinking about delivering value to customers."
"There has to be a better way to deliver value consistently without causing setbacks for the business."
" I think the tricks for scaling are rapid decision making and how you invert the decision when you make it wrong. The more you hang on to a wrong decision, the worse the impact is."
"Current Health provides a platform to enable care to be delivered at home."
"Our job was to operationalize care at home programs, and that required a whole new set of tools and thinking."
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Leadership in government and technology requires not only innovative thinking but also a deep commitment to public service. Today's guest, Paola Santana, exemplifies these qualities as she shares her journey from law and politics to becoming a trailblazer in government technology.
Paola Santana is a lawyer, public procurement expert, and serial tech entrepreneur who is revolutionizing government systems. As the founder and CEO of Glass, she is pioneering G-commerce, a new way for governments to procure goods and services. Her prior experience includes co-founding Matternet, a company leading the way in drone logistics networks. Under her leadership, Matternet worked with the White House, U.S. Congress, and NASA to establish the first U.S. drone regulations, leading to the first drone delivery platform authorized for permanent operations over a populated city.
In this episode, host Barry O'Reilly invites Paola to discuss her remarkable journey, from her early career in law and government to her groundbreaking work in technology. Paola offers insights into the challenges and opportunities of transforming public systems through entrepreneurship, emphasizing the importance of agility, data-driven decision-making, and the crucial role of small businesses in economic development.
Key Takeaways:
Additional Insights:
Episode Highlights:
The first thing is that for the level of clarity that someone like me has, where I've always known or carved moments to get very clear on where I wanted to go..."
"I love this saying attributed to Steve Jobs: You can only connect the dots looking backwards."
"Glass is literally the name that came very intuitively to me, and I've been unpacking what the name of Glass means."
"Entrepreneurship is grueling. Like, you know, you either have results or you don't."
"The future of procurement is not procurement. The future of procurement is e-commerce."
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Leadership in digital ecosystems requires a commitment to safety, trust, and ethical practices. Our guest today, Dave Byrne, founder of Trust Raise and a member of the Irish Digital Board, shares his journey from major tech giants to establishing a company dedicated to improving the integrity of digital platforms.
Dave Byrne has had an illustrious career, holding significant positions at Google, TikTok, and Spotify, where he spearheaded initiatives in brand safety and platform integrity. Now, as the founder of Trust Raise, he focuses on helping smaller companies navigate the complex landscape of digital safety. His work is driven by a deep commitment to creating ethical digital ecosystems that prioritize user needs and improve industry standards.
Host Barry O'Reilly invites Dave to discuss his career journey, the challenges of maintaining digital safety in a rapidly evolving industry, and the inspiration behind founding Trust raise. Dave shares valuable insights into the importance of adaptability, the evolving role of AI in digital safety, and how smaller companies can leverage his expertise to build safer digital platforms.
Key Takeaways:
Additional Insights:
Episode Highlights
“This career in Google, TikTok, Spotify was not at all planned whatsoever... I actually ended up in Google because I lost a student union election in Trinity College."
"The Adpocalypse... Brand safety became something that YouTube started caring about, Meta started caring about."
“ we're eroding brand perception of our customers. Again, scary things for any business to be facing, never mind the scale of the brands you're going to be working with within Google at the time.."
" I think when people think of the digital ecosystem, they think of the Googles, they think of the metas, they think of the TikToks of the world. And yes, they take up a huge amount of people's time and engagement but there are thousands of companies that make up this ecosystem, like just the ad ecosystem itself."
" AI and the tools that we're seeing are democratizing like these skills and like the ability for these folks to actually participate in, in areas where they couldn't have before."
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Cybersecurity is an ever-evolving field that requires continuous learning, adaptability, and a deep understanding of both the technological landscape and human behavior. Today’s guest, Dave Mahon, a seasoned cybersecurity expert with extensive experience in both the private and public sectors, shares his journey from the FBI to leading global cybersecurity efforts in the corporate world.
Dave Mahon served as a Senior Advisor for Deloitte, where he was instrumental in developing and executing strategies to safeguard information, technologies, and data. Prior to Deloitte, he was the Global Chief Security Officer for CenturyLink, now Lumen Technologies, and also served as a Special Agent for the FBI, focusing on federal crimes involving cyber threats, terrorism, and more. In this episode, Dave discusses the critical thinking skills he developed over his 20-year career in the FBI and how he applied them in the private sector to tackle emerging cybersecurity challenges.
Host Barry O'Reilly invites Dave to explore his career journey, the lessons he learned, and the importance of mentorship, team building, and strategic thinking in cybersecurity. The conversation delves into the nuances of transitioning from public service to corporate leadership, the evolving nature of cyber threats, and how businesses can better prepare for future challenges.
Key Takeaways:
Additional Insights:
Episode Highlights
"There's a couple of key parts of everybody's life... because it starts to set the foundation for how you think about your life going forward and how you're going to make the decisions."
"And all the standard corporations were there that you could imagine... and ultimately get hired by the FBI."
"So I literally went undercover for four years... and next thing I know, I was doing computer forensic work."
"A couple of things you start to realize around cyber that was so very different... there was a lot of learning."
"You have to understand people... and what motivated them at what stage they were in their career."
"Bad guys don't go away, they innovate... we need to be moving in cyber to stay ahead."
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Innovation and Inclusivity in Motorsports are about breaking barriers, fostering innovation, and making the sport accessible to all. Today's guest, Rob Smedley, founder and CEO of the Smedley Group, shares his journey from Formula One engineer to entrepreneur, revolutionizing the motorsport industry.
Rob Smedley is known for his work with top Formula One teams like Ferrari and Williams. Using data technology to drive innovation, Rob has now embarked on a new venture to create a global karting league, making motorsports accessible to a wider audience. His career is marked by his commitment to innovation and his belief in the potential of young talent.
Host Barry O'Reilly invites Rob to discuss his path from a disengaged student to a top engineer and now an entrepreneur. Rob shares valuable lessons on embracing discomfort, committing to goals, and continuously innovating. The conversation highlights the importance of inclusivity in motorsports and the exciting future of the Global Karting League.
Key Takeaways:
Additional Insights:
Episode Highlights
"Commit to something, don't be scared and figure it out as, as you go along."
"I wasn't a great student at school. I absolutely was a terrible student."
"If you're not uncomfortable, you're probably not trying hard enough."
"Innovation is just embedded in the business of Formula One."
"We've taken about 95 plus percent of the costs out of it."
"I've had to unlearn coming into what I would call the outside world."
"What I'm most excited about is team work, right? I love being part of a really strong, high performing team."
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Leadership is about embracing sustainable practices, fostering continuous improvement, and aligning personal values with professional goals. Today's guest, Annastiina Hintsa, CEO of Hintsa Performance, shares her insights on achieving peak performance in both business and sports.
Annastiina Hintsa is the CEO of Hintsa Performance, a world-leading evidence-based coaching company that helps top athletes and business professionals achieve sustainable success. Driven by science and guided by people, their methods have been tested in some of the most challenging business and sporting environments. Annastiina's journey began with her father, Dr. Hintsa, whose pioneering work with athletes like Haile Gebrselassie laid the foundation for their holistic performance model. Annastiina has expanded this legacy, working with over 50% of Formula One drivers and Fortune 500 CEOs, ensuring they reach and maintain high performance.
Host Barry O'Reilly invites Annastiina to discuss her journey and the impact of Hintsa Performance. From her early involvement in the company to her leadership role today, Annastiina shares valuable lessons on balancing professional and personal well-being. The conversation covers the holistic nature of high performance, integrating physical activity, nutrition, mental energy, and more. Annastiina emphasizes the importance of defining personal success and maintaining perspective through life's challenges.
Key Takeaways:
Additional Insights:
Episode Highlights
"I worked with my dad early days. I was employee number three in the very, very early days..."
"when my father got sick. So he was, uh, he was diagnosed with pancreatic cancer in 2015, passed away 16 months after. And it was a turning point for for me personally"
"Our mission is to help people live better lives and as a consequence, perform better..."
"We get stuck in the middle gear. We get stuck in this kind of like execution mode where we're constantly just, you know, yeah, we're not we're not at our peak. We're also not recovering and resting. We're at this middle gear checking our emails, you know, responding, uh, executing. But when the time comes, when we would actually need to get to that high gear, get to the peak performance"
"how do we make sure that we as humans are ready for that shift?"
"start with the critical questions and you start with that. Do you know who you haven't really think of? Who are you as a person, not just you at work or your job title. How do you actually define success? What is it that you really want? What are the different points of success for you? And then the final question is around sort of control, which is as much as it is about, you know, what are the things that we can control and we can influence."
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Leadership is about embracing the process of unlearning outdated practices, fostering a culture of continuous improvement, and aligning your team with visionary goals. Today's guest, with his esteemed 29-year tenure at one of the largest asset managers in the world, Vanguard, shares how he successfully navigated this journey.
John T. Marcante is a renowned technology and business executive with expertise in digital transformation, business strategy, financial planning, and cybersecurity. He is the US CIO in Residence at Deloitte, providing strategic guidance to clients and leadership.
Previously, John was the Global CIO at Vanguard, where he led digital transformation and drove growth to $9 trillion. He modernized Vanguard's technology and promoted an inclusive workplace. He also developed Vanguard’s global advice platform, making financial planning accessible to millions.
John has contributed to the WSJ CIO Journal and Harvard Business Review. His awards include Business Insider Top 50 CIOs and ORBIE CIO of the Year. He holds degrees from The Pennsylvania State University and Saint Joseph’s University.
Host Barry O'Reilly invites John to share his journey at Vanguard and beyond in leadership, culture transformation, and gratitude. Inspired by his father's legacy in technology, John discusses how he aligned tech with business goals at Vanguard. Barry highlights John’s approach to direct client engagement and open feedback. They also explore John’s commitment to servant leadership, maintaining company values, and his future goals of mentoring new leaders and giving back to the community. This episode offers personal insights into what drives effective leadership with gratitude.
Additional Insights:
Episode Highlights:
00.00 - Introduction to the episode
02:58- John's reflections on recent thoughts and his father's influence on his career
"I think the last thing that popped in my head since we just went through Father's Day, as I was kind of reflecting on my own father…"
05:29- Cultural transformation and leadership at Vanguard
"So I think I go back to a point you just made, which is, if this transformation is a technology transformation, if it's a technology initiative, then it's already lost, right? Because nothing's a technology initiative. Everything is, a business, a client transformation and that alignment..."
05:53- Leadership and servant leadership in transformation
"I always felt like that the transformation was a C-suite and CEO-led transformation. You know, technology, lean, agile. They'll roll out across the company, not just in technology, but across the company really took that level of focus and alignment."
15:00-Engaging and aligning with clients
"if you want to drive engagement and give a group of people an outcome that's meaningful to clients and give them access to clients, and you said, yes, it's a wonderful when they when they could do something, they see the impact."
15:21- Feedback on improving processes and client satisfaction
"And if you have a nimble, very, very nimble foundation that allows you to very quickly take that feedback and turn it."
18:38- Dealing with high-stakes decisions and maintaining company values
"Not every business is good business. Stick to your mission and purpose, and always have your clients' and employees' backs."
20:47 Discussing the importance of mission alignment in leadership
"It's also you feel connected to the mission of the organization. Like what I do every day has to be connected. But the mission, I have to sleep well at night knowing that the company has my back, but more importantly, that I'm actually doing good for society."
21:45- Personal anecdotes on handling client interactions and maintaining values
"this is one of the things I think that, uh, again, it shines about the company. Like sticking to the values, leaning into your principles, I know, and making tough decisions around that.."
23:52- Building Trust Through Commitment to Solutions
"And even if you don't know the answer that you know you're committed to getting the answer, I think you then build trust in the organization."
25.45- Servant leadership and employee engagement
"If your intention isn't good and you make a mistake, well, then we'll deal with that later, right? But if you're doing work for a client and your intention is good that you have nothing to worry about, even if it goes south..."
32:34- Embracing Grace as a Core Mission in Leadership
"I think as a father, that's our mission as a leader. That's our mission. Like, be gracious, you know, be gracious even when someone doesn't hit the record button"
35:09- Transitioning into a new chapter and future plans
"I want to be part of, uh, coaching and developing the next generation of leaders that I want to be part of that team, whatever team that is. Count me in, because that was the best part of my job. Second technology. I mean, like, come on, like, I mean technology, AI, generative AI."
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AI is transforming the world, and William is working on how IP is impacted in an AI world…
William Carbone is an AI expert, former IBMer, and now a seasoned entrepreneur with over a decade of experience in aerospace, quantum computing, and AI.
At IBM, William’s main focus was to identify opportunities, driving business & technology strategies and roadmap for the industries worldwide. He led the Business Development for IBM's Global Automotive, Aerospace & Defense industries.
Currently, William is the CEO and co-founder of Evalify, a flagship venture under Nobody Studios, and the CEO and co-founder of The Adjacent Possible. He also serves as the Program Director for the Master in AI at the Rome Business School (RBS) and advises the European Commission as a senior consultant. From creating an innovation studio to developing cutting-edge tools for intellectual property assessment, His work spans Quantum, Spacetech, AI, and various domains.
In this episode hosted by Barry O’Reilly, William discusses his journey, including his transition from corporate life and the transformative experiences that shaped his entrepreneurial path. He delves into the practical aspects of innovation and intellectual property, offering advice on navigating these complex areas. This episode is packed with insights for anyone looking to improve their approach to entrepreneurship and understand the value of mental health in the process.
Key Takeaways from the episode include:
Additional Insights:
Episode Highlights:
(00:00) Introduction to the episode
(01:25) Importance of rewiring the brain and transformative journey of entrepreneurship
[01:43] “There is no one making things for you… You have to take the tools on the way and find the way.”
(02:23) William shares parallels between learning music and his entrepreneurial journey
[3:53] “Music has always been there for me in the journey, even in difficult times or more challenging situations.”
(05:14) Barry discusses the importance of following curiosity in entrepreneurship
[7:39] “There was a lot of untapped potential in that space, like in billions of dollars that have been spent on patents that have been just never commercialized…”
(08:35) Introduction of E-Verify and its capabilities in de-risking investments
(11:43) The evolution of AI and its impact on intellectual property assessment
[13:22] “But the biggest unlearning there was how to make the industry, to unlearn how they approach LLP. That was the biggest challenge, right.”
(13:23) The challenges and benefits of helping the VC industry unlearn traditional approaches to IP
[14:27] “I would say the biggest challenge for us and for the investors is to understand that the IP can be a valued friend and partner…”
(15:17) Barry shares his experiences with continuous delivery and automation in software development
[17:34] It's not that we're taking the humans out of the process, it's we're allowing them to focus on high-value tasks…”
(19:10) The concept of patent viability assessment and its impact on investment decisions
[21:13] “So these are all great indicators that are simply not available, or maybe no one has the intuition to look for them and find competitors for a startup.”
[22:03] “Some investors will tell you.. revenue speaks louder than IP. Others say, okay, IP is so fundamental.”
(24:13) William's vision for the future of IP and entrepreneurship
[25:29] “There is already a populated market in the direction that you haven't seen before with your business analyst.”
(26:27) The democratization of patent information and its impact on founders and investors
(30:39) William's entrepreneurial journey and the importance of mental health retreats
[30:48] “Actually what is not so much covered is mental health or founders - I would say that's the number one priority.”
(33:29) The importance of balance and intention in life and work
[34:48] “We live in the attention economy, like everything, trying to grab our attention.”
(35:35) Conclusion and final thoughts from Barry and William
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The definition of success can change everything. Properly defined, you have an agile organization where each team member can contribute fully. Poorly defined, you have stagnant teams and users that don’t like the products. In this episode of the Unlearn Podcast, host Barry O'Reilly sits down with Josh Seiden, a sought-after designer, strategy consultant, and coach. Together, they explore the importance of understanding user behavior, how that behavior can be translated into goals, and how company alignment on Outcomes and Key Results can drive business outcomes.
Josh Seiden has collaborated with top-tier brands such as PayPal, Johnson & Johnson, and 3M. His expertise lies in launching and building innovative products and services, as well as fostering agile and entrepreneurial mindsets within organizations. He is the author of “Outcomes Over Output” and co-author of “Who Does What By How Much,” "Sense and Respond," and "Lean UX," all cementing his reputation as a thought leader in the field of user-centered design and business strategy.
When User Experience Became Design
We know now that understanding how users will experience a product is a critical part of designing a new product, but back in the 90’s when Josh began his career in the industry, it was a radical idea. "A friend told me, 'We’re hiring designers here,' and I laughed, 'Why are you telling me this? I’m not a designer.' But that thing you’re doing here, we call that design," Seiden recalls. This unconventional designation became an entire industry, and his unconventional path to it meant he brought a unique perspective to the field of user experience design. Barry notes that this is a story that gets told again and again on the Unlearn podcast; that the conventional wisdom on how to find or become an expert is often wrong.
Don't Forget Why You’re Building What You’re Building
Barry points out that companies often measure things like the speed of production, but forget to measure the consumer behavior change that would really demonstrate the value of the project. Josh explains that measurability is important over the life of a project, but keeping the focus on outcomes for actual people is the most important thing to track. This is the key premise of Outcomes over Output that answers the question: what is an outcome? Josh’s definition, “An Outcome is a measurable change in user behavior that creates value.” If you need to identify the outcome you should be measuring for your company, answer three questions: Who?, Does What?, and By How Much?
The Evolution of OKRs in Large Organizations
Design thinking works at the team level very easily, and as the industry developed the question became how to do it at scale? Objectives and Key Results (OKRs) have emerged as a tool for helping large organizations work in agile ways. Josh explains how OKRs can be used to manage outcomes at scale: “The O is an objective. What's the big audacious goal? And then the KR is the result. How do you measure it? The key result. For most people who look at the system, they understand that [...] you want those Key Results to be outcomes." This way of thinking helps large enterprises maintain focus and drive impactful results by clearly defining and measuring success as it matters to the people using the product.
Read full show notes at BarryO'Reilly.com
Resources
Josh Seiden on the Web, LinkedIn, X, Medium
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