CTO Confessions Brought to you by IT Labs

When one operates in an extremely sensitive, heavily enforced, compliant environment, there is lots of work to tick the boxes and jump through required hoops. This is the case in the social services that are there to care for the well-being of people. This often results in many people who should be delivering care being redirected to administrative tasks, such as updating records and ensuring the correct steps are taken. A process on steroids that has to be fully auditable. In this episode, TC Gill, the Chief talking Officer (CtO) of the podcast series, sits down with a tech leader with a passionate mission in this space. Gary Pyke joins us to describe the challenge he and his teams address for the benefit of the people that deliver care and those that receive it. A really insightful discussion, with many takeaways for tech leaders and leaders in general. Key takeaways from the podcast are: • Getting clear and agile on the outcomes you are trying to solve • The magic of big-hairy-audacious goals • Avoid being data-rich and insight poor • Getting creative around compliance Our Guest: Gary Pyke LinkedIn: https://www.linkedin.com/in/gary-pyke/ Website: Vale of Glamorgan Council: Overview

Tax compliance, it turns out, is an edgy space to operate in. For example, at scale, manual handling of receipts and invoices can be a costly endeavor, and many large organizations default to safer shortcuts that prevent tax that could be claimed from being processed. It's a complex problem to solve with many variables that are at play. The scream for automation has been heard by "Blue dot." A Fintech company that has solved the headache through elegant automation. i.e., automated tax compliance systems that create healthier bottom lines. TC Gill, the host of CTO confessions, sits down with David to dig a little deeper into the details and the "why's" of why this is such a challenge. He also gets to go deep with David on his leadership insights and the art of enhancing communications in service of the collective work. A deep and thoughtful tech leader with some great insights to take away. Key takeaways from the podcast are: • The concept of "Forcing communications" to create transparency and better understanding in and around the teams • An anthropological view on the art of communication • Inspiration to be more grateful for the world around us and the work we do as technologists Our Guest: David Guedalia LinkedIn: https://www.linkedin.com/in/david-guedalia-565a374 Website: https://www.bluedotcorp.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

The stereotypes say that sports and tech don’t go well together, but the reality is, that tech has taken all sports to the next level. From gathering game data to performance analysis all the way to getting insight into what’s happening on a field – the marriage between sports and tech has been rather spectacular. In this episode, I talked with Ben Burdsall, CTO of one of the biggest sports technology companies in the world, Sportsradar – and we talked about it all: from his beginnings, through his learning process, and how he was shaped as a leader, all the way to what he does now with Sportsradar. Key takeaways from the podcast are: • Why putting people first will help reduce potential depersonalization in big companies • How the concept of “mean time to innocence” can actually help businesses locate issues and respond faster • Why diversity in all its forms can help growth and well-being at workplaces Our Guest: Ben Burdsall LinkedIn: https://www.linkedin.com/in/ben-burdsall-6ba2bb/ Website: https://sportradar.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

In today’s vastly connected – almost intertwined – world, we know that transportation and mobility play a crucial role in maintaining the flow of life as we know it. So, is it any wonder that the technology and operations that are at work in the industry are the brainchildren of some of the best tech leaders out there? I got one of these tech leaders to sit down for a friendly-but-insightful talks – meet Kirk Franzen, the CTO at Cargo Chief, a company that works in the freight market, using tech to reduce headaches that stem from logistics. I and Kirk talked in depth about Cargo Chief, his journey to becoming a tech leader, and the way that he likes to get things done. Key takeaways from the podcast are: • Why allowing people to make mistakes can be very benefix`cial in the long run • How helping people learn what they want can be a catalyst for real change • Why taking a step back or just being patient is sometimes better than just going for something Our Guest: Kirk Franzen LinkedIn: https://www.linkedin.com/in/kfranzen/ Website: https://cargochief.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Time – it's the one thing that no one can’t control, no matter their skill or know-how. And for small and medium businesses, getting the needed protection and insurance in time is essential. Meet Shay Mandel, VP of Engineering at Next Insurance, a company that provides insurance to small and medium-sized businesses at the click of a button, instead of waiting for weeks as it usually goes in the market nowadays. So how is Next Insurance doing this? How did Shay get to where he is? The answers to these questions and many more were answered in this episode, as our TC Gill sat down with Shay to dive deep in all matters of business and tech.> Key takeaways from the podcast are: • Why technical debt is not something that should be overlooked • How code has a way of showing you where progress and development can hit a snag • How technical debt can actually influence people’s decision to come on board Our Guest: Shay Mandel LinkedIn: https://www.linkedin.com/in/shaymandel/ Website: https://www.linkedin.com/company/nextinsurance/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

As any tech leader looking to make their own path and do their own thing know that all their experience and knowledge will be fruitless, unless the idea they build on doesn’t improve the livelihood of people. In an age where everything seems to be already discovered, tech leaders like Brent Williams, CEO at Benekiva, come to the fore to show us that we’re wrong, and that there’s still much that we don’t know. Listen to his convo with TC, as they dive deep into Benekiva’s doings, as well as Brents journey to becoming a tech leader. Key takeaways from the podcast are: • How you can find opportunities in problems • Why going against nay-sayers can actually be more rewarding than just falling in line • How learning from great leaders can help you develop your perspective and approach Our Guest: Brent Williams LinkedIn: https://www.linkedin.com/in/brentewilliams1/ Website: https://www.benekiva.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

With everything getting digitized and slowly moving on to the virtual world, there are some industries and arts that are having a bit of a hard time adapting to the new normal. Sales are one of them. Making sales is hard to pull off in-person, and even harder to pull off online, but people like Chuck Hardy, Head of Engineering at Salesroom, have made it their goal to make it easier for people to reach their potential clients, and remove the obstacles that selling in virtual environments pose. TC sat down with Chuck to learn more about Salesroom, about his own journey to becoming a tech leader, and what drives him. Key takeaways from the podcast are: • The highest level of competency is knowing what you don’t know • The importance of staying humble • Bridging the skills gap is all about bringing the concept of learning to life Our Guest: Chuck Hardy LinkedIn: https://www.linkedin.com/in/chuckjhardy/ Website: https://chuckjhardy.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

How would one define tech leadership? Is it all about innovation? About creating something that will serve humanity as a whole? Or maybe it’s about empowering people and nurturing them to become leaders on their own? It’s all of the above, and much more – but the one thing that drives our guest, Knowledge Officer’s founder, Ahmed El-Sharkasy, is to provide the platform for people who are looking to develop and improve their skills and become better at what they love doing! TC Gill sat down for a chat with Ahmed, to pick his brain on the important bits – his journey to becoming a tech leader, the way he operates, and what drives him – day in, day out. Key takeaways from the podcast are: • The highest level of competency is knowing what you don’t know • The importance of staying humble • Bridging the skills gap is all about bringing the concept of learning to life Our Guest: Ahmed El-Sharkasy LinkedIn: https://www.linkedin.com/in/elsharkasy/ Website: https://www.knowledgeofficer.com/ Twitter: https://twitter.com/Ahmed_Sharkasy Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Healthcare is a sensitive topic around the world, as it becomes bigger, and significantly more complex – not just from a technological perspective, but also from a financial and business as well. Enter Firefly Health – a virtual-first healthcare company that’s all about making healthcare more affordable and easier to navigate. Our TC Gill sat down with the company’s CTO, Mimi Liu, to talk about the company, her journey to where she is today, and how she goes about leading her teams! Key takeaways from the podcast are: - How important it is to see opportunity in crises - Why diversity is not just about the difference in character, but also in how we handle and see stuff - How tech can empower people in navigating their way through anything Our Guest: Mimi Liu LinkedIn: https://www.linkedin.com/in/msliu/ Website: https://www.linkedin.com/company/firefly-health/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

The third installment of our Stories of the Amazonian Tribe is here! For this one, we have Joe Trelin, an Amazon “recidivist”, meaning he had multiple “tours” with the company, working in various departments and in different positions. Charles sat down with Joe to talk about his time with Amazon, as we take a peek and a view on the culture inside Amazon, the processes, and learn more about the bits and pieces that make the big Amazon tick. Key takeaways from the podcast: - Everyone has a role to play in the process of innovation, and sometimes you need to be the spark that gets it all going - How to function in ambiguity and unconventional roles - How customer-centricity can impact product & service development Our Guest: Joe Trelin LinkedIn: https://www.linkedin.com/in/joe-trelin-6a89a7/ Website: https://authid.ai/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)