
CTO Confessions Brought to you by IT Labs
Hosted by TC Gill, this podcast explores the dynamic world of technology leadership. Each episode explores the challenges, strategies, and stories that shape the lives of today’s CTOs and tech leaders.
From navigating complex business issues to leading high-performing teams, CTO Confessions sheds light on the multifaceted role of technology executives, highlighting the critical decisions they make and the impact they have on organizations.
Join us as we unpack the realities of tech leadership and share insights that rarely get the appreciation they deserve, all with a healthy dose of curiosity and candor.
Brought to you by IT Labs.
Latest episodes

Sep 28, 2020 • 1h 6min
Episode 11: CTO's Voice From The Banking As A Service Industry With Taylor Lilley
Episode 11: CTOs voice from the Banking as a Service Industry With Taylor Lilley
CTO's voice from the Banking as a Service Industry - Setting up high performing resilient remote teams and architectures
Tech leaders today are multi-faceted. There is the obvious requirement to understand technology, at least from a high level, but also a need to be business-minded and understanding what creates the best high-performing teams in one's leadership scope.
In this episode, Taylor Lilley joins us to give us an insight into his lessons over varied his journey. Taylor is the CTO at White Label MFG with a straight-talking style that gets the nub of where the challenges are and what the options are. Rewinding his timeline on experience, you get to see a colorful journey, one that started in the United States Marine Corps.
Key takeaways from the Podcast are:
Try not to treat your highly intelligent engineers as task doers (get the best out of your high IQ people)
Communications is the key to making remote teams deliver the outcomes you want
High-level tips on creating high volume resilient architectures
The importance of having a business head as well as a tech one
Our Guest: Taylor Lilley
LinkedIn: https://www.linkedin.com/in/taylor-lilley/
Website: https://www.whitelabelmfg.com/
Twitter: https://twitter.com/whitelabelmfg
Our Host: TC Gill
LinkedIn: https://www.linkedin.com/in/mrtcgill/
Email: tc@it-labs.com
Intro and background music: Craig MacArthur - Power Shutoff (https://www.youtube.com/watch?v=x74iB_jtauw)

Sep 14, 2020 • 36min
Episode 10: CTO’s Roles In Driving Revenues For SaaS Companies With Gene McNaughton
CTO's role in driving revenues for SaaS Companies - In sales, seemingly small things can make a huge difference.
Selling is an art, and like any art, we can use techniques to improve or suppress the probability of creating the desired result. In the modern world and COVID19 crisis, interactions in the digital world are becoming the norm rather than the exception. The normalities of face to face meetings have, at least for the short term, turned into a rarity. Thus, impacting the ability to develop a healthy rapport between the seller and potential client. Gene, a thought leader in the space of sales and company growth, shares his wisdom on how technology leaders can set up their sales representatives to tip the scales towards success. What appears to be small things can make an impact on online meetings, which smooth the path towards a sale or, at a minimum, a stronger client relationship. Gene is an author on the art of selling, who has lots of experience working with many large organizations to drive revenue growth, and a man with many years of experiential success for his clients. So, what Gene has to say to Tech leaders holds weight. His advice will help your organization's bottom line.
Our Guest: Gene McNaughton
LinkedIn: https://www.linkedin.com/in/genemcnaughton/
Twitter: https://twitter.com/genemcnaughton
Intro and background music: Craig MacArthur - Power Shutoff (https://www.youtube.com/watch?v=x74iB_jtauw)

Aug 31, 2020 • 37min
Episode 9: CTOs as Champions for Innovation with Jeremy Basset
CTOs as Champions for Innovation - Providing innovation to enterprises in uncertain times
Large cooperation's attempt to innovate internally, sinking vast amounts of money, balancing high levels of risk, and rarely succeeding in achieving the innovation opportunities they crave. So what can tech leaders within these organizations do?
Jeremy Basset, Founder and Managing Director of CO:CUBED, joined us for a conversation on how CTOs and tech leaders can be the champions of innovation by taking a rather different approach to invigorate innovation in an easy, de-risked way.
Quote
“... we're going into a new era now where it won't be... step-change transformation, but just ongoing incremental innovation that happens every day and over the medium to long term. [i.e. consistently] deliver[ing] ongoing transformation.”
Key takeaways from the Podcast are:
How can tech leaders of large enterprises maximize their ability to innovate?
How can corporates make innovation easy for themselves?
Our Guest: Jeremy Basset
LinkedIn: https://www.linkedin.com/in/jeremybasset
Intro and background music: Craig MacArthur - Power Shutoff (https://www.youtube.com/watch?v=x74iB_jtauw)

Aug 14, 2020 • 1h 18min
Episode 8: Transformation for Innovation with Deal Daly
Transformation for Innovation with Deal Daly: Technical leaders part in the Innovation Game
As a tech leader, how do you transform your organization for innovation? And why you need to be involved in the first place?
Deal Daly, Field CTO at Hammerspace (https://www.linkedin.com/company/hammerspace/), joined us for an enlightening conversation on the subject. With many years in mergers and acquisitions, looking at technology from the outside-in. His journey gradually led him to lead infrastructure groups. For this reason, Deal has a very interesting perspective. He's a business person with an acquired technology angle. Now looking from the inside-out, he shares his learning and insights.
Key takeaways from the Podcast are:
• Why must technology leaders become partners in enabling the entire business, not just in the capabilities of a product?
• How tapping into the inherent curiosity of technical people can drive team performance and innovation.
• Using the multiplier effort to drive and spread innovating behaviors.
Our Guest: Deal Daly
LinkedIn: https://www.linkedin.com/in/dealdaly101/
Intro and background music: Craig MacArthur - Power Shutoff (https://www.youtube.com/watch?v=x74iB_jtauw)

Jul 24, 2020 • 1h 6min
Episode 7: A CTOs Epic journey with Charles Griffith
Welcome again for another tech leader's confessions. That right its a CTO Confessions podcast. This episode focuses on the journey of CTOs and, in particular, the expedition of Charles Griffith. An experienced CTO with an interesting passage from:
- Gaming industry
- To working at Amazon in the formative years
- And then to a Startup … and Exit
Be inspired to find the path for your journey and see how making it varied can lead to long term success. Creating a well-rounded tech leader. Investing in your journey from a place of awareness is a powerful leader trick to lead you to places where you want to be, rather than where you end up.
Our Guest: Charles Griffith
Linkedin: https://www.linkedin.com/in/charlesgriffith
Intro and background music: Craig MacArthur - Power Shutoff (https://www.youtube.com/watch?v=x74iB_jtauw)

Jun 15, 2020 • 31min
Episode 6: CTOs Role in Driving Sales & Marketing Alignment with LaCosta Lolly
Greetings again for another installment of the CTO Confessions podcast. This episode focuses on the important role CTO's play in driving Sales and Marketing alignment. Our guest is LaCosta Lolly from GrowthSmart Consulting.
Key takeaways from the Podcast are:
How technology leaders can take Sales and Marketing to the next level!
The importance of tools and data strategy to support (not hinder) Sales and Marketing.
How a lack of alignment in sales and marketing can lead to disjoints in other parts of the business.
The importance of getting this right in organizations cannot be understated. You the CTO, have an integral part to play in helping Sales and Marketing align In their approaches.
So my challenge to you Technology Leaders out there is first listening to the Podcast. Secondly, see how the technology solutions you are supporting (or creating) can be repurposed to form alignment, rather than disjoints in the organization. Sales & Marketing and the organization as a whole will thank you for it in the end. Hey, it most probably will make your life easier as well.
Our Guest: LaCosta Lolly
Linkedin: https://www.linkedin.com/in/lacostal/
Twitter: https://twitter.com/lacostalolly
Growthsmart: https://twitter.com/GrowthSmart
PowerPoint slides used in the Video Podcast:
https://www.it-labs.com/wp-content/uploads/2020/06/CTOs-Role-in-Driving-Sales-and-Marketing-Alignment-by-LaCosta.pdf
Intro and background music: Craig MacArthur - Power Shutoff (https://www.youtube.com/watch?v=x74iB_jtauw)

Jun 2, 2020 • 42min
Episode 5: Transformation Leadership for CTOs Jardena London
Once again, greetings, ladies and gentlemen. Jardena London joins me for a riveting discussion on Leading Transformations. On how exciting they are, and at the same time how painfully challenging they can be. In short, It's not for the faint-hearted.
Some of you may recall Jardena from a previous IT Labs Webinar: "Creating Structural Agility with Living Systems.", jointly presented with Sally Breyley Parker.
In this talk, we dig deeper into the role of CTOs in organizational transformations. We cover a number of angles including a few outlined here:
- The elements that create good transformation. What supports transformation and what does not.
- What Jardena has observed in her vast experience
- And the importance of the CTO and tech people in enhancing transformations.
Something in our discussion resonated with me. On how we need to get more of the technology folk talking to the business and supporting them. Especially CTOs. It's been something that I have been banging the drum about for a long time. Jarndena's view reinforced my belief that we need to break down boundaries with CTO's leading aspects of a transformation from their wealth of intellect, ideas, and passion for trying new technological ideas.
I hope you come away with as many good takeaways as I did.
Our Guest: Jardena London
Linkedin: https://www.linkedin.com/in/jardena/
Twitter: https://twitter.com/Jardena
Referenced Webinar in the Podcast: Creating Structural Agility with Living Systems (Guests: Јardena London & Sally Breyley Parker): https://www.youtube.com/watch?v=pX0MXomfrrE&t=14s
Intro and background music: Craig MacArthur - Power Shutoff (https://www.youtube.com/watch?v=x74iB_jtauw)

May 14, 2020 • 35min
Episode 4: Client Confessions – DonorTrends Success story with Ben Miller & Caity Craver
Episode 4:
DonorTrends Success story (from Innovation to conception, and a lovely happy exit)
Greetings again ladies and gentlemen, and variations thereupon. We have a special episode for you this time, the first in a series. We are calling them “Client confessions” where we invite current and previous clients of IT Labs to talk about their projects, businesses and where they are with them. The aim is to deliver insights and stories of success (and maybe even failures), this all being in in the spirit of providing value and shared learning. Anyway, back to this Client Confessions Podcast.
It was a delight to talk to Caity Craver & Ben Miller from DonorTrends about how they took an idea for helping non-profit organisations maximise donations to realisation. This was through a heady mix of sophisticated maths, big data analysis, a sprinkle of AI and inventive ways of presenting the information. A remarkable story of Innovation, conception to successful exit. And along their journey was IT Labs, turning a very manual time-consuming process into a product that was a win for everyone. This makes all of us at the office incredibly proud. We invite you to listen to their account. I hope you enjoy the discussion as much as I did.
Our Guests: Ben Miller & Caity Craver
Linkedin:
Ben Miller: https://www.linkedin.com/in/ben-miller-737b8/
Caity Craver: https://www.linkedin.com/in/caitycraver/
Intro and background music: Craig MacArthur - Power Shutoff (https://www.youtube.com/watch?v=x74iB_jtauw)

May 6, 2020 • 34min
Episode 3: Automobile eCommerce industry amid Corona disruption with Eugene Kovshilovsky
Hello, again, people. I hope you are keeping safe out there with the continuing Coronavirus drama. It turns out our next CTO Confessions podcast is in part once again related to the subject of navigating an organisation during these times.
Eugene Kovshilovsky (Евгений Ковшиловский), Senior Vice president of Engineering at US Auto parts, joins me for a discussion around how the automobile eCommerce industry is handling the Coronavirus storm. Eugene has vast experience across many sectors and carries a nice mix of technological wisdom, knowledge and skill, with the leadership qualities that bring his teams together (the human element).
The turmoil has shaken all layers of the Automobile industry. In the podcast, we discuss how the auto parts eCommerce industry works. I enter the discussion with Eugene, curious as to see how things have impacted it from a technological perspective.
Our Guest: Eugene Kovshilovsky
Linkedin: https://www.linkedin.com/in/kovshilovsky/
Twitter: https://twitter.com/EKovshilovsky
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Apr 23, 2020 • 41min
Episode 2: Principles for the foundation of technology-driven organisations with Banne Gjorcevski
Episode 2:
Principles for the foundation of technology-driven organisations - Herding the kittens in technology
Hello People. I hope you are managing to navigate yourself, your people and your organisation through these mind-boggling times. Our next CTO Confessions podcast is highly related to this subject of navigating an organisation in general, particularly in these times. That's leading others and includes leading yourself.
Banne, CEO and co-founder of IT Labs is joining me in a warm discussion on the subject. We are going to get together with a hot beverage and talk about Principles (and values) that help drive what you as a leader are trying to achieve. How principles combined with your unique style of leadership support you in herding those kittens in your organisation that just seem to run off in a different direction than don't serve you or the business very well. We will gravitate around a book that we both love (Principles by Ray Dalio). Principles are powerful. They help you make tough decisions; they allow people to align themselves around them. They can create a powerful flow of value delivery and productivity with minimal command and control (i.e. make your life easier). Come and have a listen and see how this can help your leadership and the dynamics in your workplace.
Our Guest: Branislav Gjorcevski
Linkedin: https://www.linkedin.com/in/branislavgjorcevski/
Twitter: https://twitter.com/bannegjor
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)