Story of a fractional CTO with Thanos Diacakis

Story of a fractional CTO with Thanos Diacakis

Author: PM Power Consulting July 12, 2025 Duration: 53:38

My guest today is Thanos Diacakis, Software Delivery Coach & a Fractional CTO.

We covered a wide range of topics that included:

  • Insightful Experiences: Thanos shared many insightful and thought-provoking experiences and perspectives, particularly on software delivery life cycle improvements without explicitly using terms like Kanban 
  • Balancing Work and Personal Life: Thanos emphasized the importance of balancing work and personal life, recognizing that while work is important, personal relationships and leisure activities are equally significant.
  • Fractional CTO Business: Thanos discussed the benefits of running a fractional CTO business, allowing for flexibility in managing time and delivering value to multiple clients
  • Scaling Challenges: Thanos shared experiences with scaling projects, particularly with Uber's bikes and scooters, highlighting the importance of having systems in place to manage growth
  • Learning from Others: Thanos emphasized the value of learning from others and cross-pollinating ideas across different clients to improve software delivery 


Thanos Diacakis helps startups and growing companies overcome software bottlenecks, scale engineering teams, and deliver high-quality products faster. With over 25 years in software development, his background spans both early-stage ventures and tech giants like Uber and Included Health, where he led the technical integration of the JUMP Bikes acquisition, scaling the platform to 45k vehicles and over 2 million monthly trips. He’s seen elite teams stall when outdated processes leave them too heads-down to course-correct. With lean, evidence-backed practices, he unlocks faster delivery and greater developer satisfaction, so velocity rises while burnout falls.


SOCIAL MEDIA LINKS:

Website:  https://www.cosmicteacups.com/

LinkedIn: https://www.linkedin.com/in/thanosd/


Behind every line of code, there's a person with a story. Software People Stories, from PM Power Consulting, moves beyond abstract theory and polished case studies to explore the real, human experience of building technology. This isn't about hypotheticals; it's a collection of candid conversations with the practitioners themselves-developers, designers, product managers, and architects-who share firsthand accounts from the trenches. They talk about the paths that led to success and, just as importantly, the unexpected detours and failures that provided the most valuable lessons. Each episode delves into the nuanced journey of discovering what users need, designing elegant systems, navigating complex development, and ultimately delivering solutions that matter. By focusing on these personal narratives, the podcast reveals the core of software creation: a blend of technical skill, creative problem-solving, and team dynamics. Listeners gain practical wisdom and relatable perspectives on the challenges and triumphs inherent in the tech industry. Tune in for an honest look at the craft, where the stories of people are just as crucial as the software they build. You'll find this podcast a refreshing source of insight for anyone involved in or curious about the technology and business landscapes, offering career lessons learned the hard way.
Author: Language: English Episodes: 100

Software People Stories
Podcast Episodes
Navigating Technological Changes with Sudipta Lahiri [not-audio_url] [/not-audio_url]

Duration: 59:50
In this podcast episode, Sudipta Lahiri, Head Of Engineering and Products at Nimblework, Inc shares his compelling journey from growing up in a cosmopolitan township and studying metallurgical engineering to becoming a l…
Tech Entrepreneurial Insights with Bhargav Bhikkaji [not-audio_url] [/not-audio_url]

Duration: 53:17
In this podcast episode, Shiv is in conversation with Bhargav Bhikkaji, a tech leader, entrepreneur, and founder-CTO of MajorDomo Inc with deep expertise in cloud and Gen-AI driven enterprise software. In this episode of…
Navigating Career Paths with Anees Haidary [not-audio_url] [/not-audio_url]

Duration: 55:52
In this podcast episode, Shiv is in conversation with Anees Haidary, Global Head, Operational Excellence, Data Privacy, and Global Workforce Management at Sasken Technologies.In this engaging episode, Anees shares his re…
Loving Failure and Learning Daily with Kumaran Anandan [not-audio_url] [/not-audio_url]

Duration: 1:02:26
In this podcast episode, Gayatri Kalyanaraman is in conversation with Kumaran Anandan, CTO of TinyMagiq and Enterprise Architect —shares a refreshingly honest journey across hardware, industrial automation, embedded syst…
From Backend IT to Frontline Digital Transformation with Shubhangi [not-audio_url] [/not-audio_url]

Duration: 45:44
In this podcast episode, Gayatri Kalyanaraman is in conversation with Shubhangi M Josiam, Digital Head APAC of Alstom about her 18+ year journey across GE and Alstom, moving from core IT and infrastructure roles to custo…
New Year message from our Hosts [not-audio_url] [/not-audio_url]

Duration: 6:21
As we step into 2026, a heartfelt thank you to all our listeners for your time, trust, and continued support. Your engagement, feedback, and encouragement mean a lot to us and inspire us to keep creating meaningful conve…
Embracing Change and Challenges with Hasan Siddiqui [not-audio_url] [/not-audio_url]

Duration: 1:01:14
In this episode, Hasan Siddiqui, a veteran in the IT industry, recounts his extensive and diverse career in the software and technology industry, offering valuable insights and advice along the way. He starts with his ac…
Curiosity-Driven Success with Ravikiran Pothukuchi [not-audio_url] [/not-audio_url]

Duration: 52:56
My guest today is Ravikiran Pothukuchi, the leader of Dassault Systèmes’ Enterprise Portfolio business in India.In this conversation, Ravi shares his journey from his humble beginnings in a small village in India to beco…
Evolving Security Practices with Ben Wilcox [not-audio_url] [/not-audio_url]

Duration: 52:05
In this episode of the Software People Stories, my guest Ben Wilcox is the Chief Technology Officer and Chief Information Security Officer at ProArch. Ben shares his fascinating journey from building a web hosting busine…
Empowering Developers with Yaron Schneider [not-audio_url] [/not-audio_url]

Duration: 36:18
In this episode of Software People Stories, Shiv is in conversation with Yaron Schneider, co-founder of Diagrid and a seasoned developer and entrepreneur deeply involved in the open source movement.Yaron shares his origi…