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imperfect: The Heart-Centered Leadership Podcast
Episode 264: Navigating the Tech Terrain: A Conversation with Douglas Squirrel

Episode 264: Navigating the Tech Terrain: A Conversation with Douglas Squirrel


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Douglas Squirrel embarked on his leadership journey as the CTO of financial software firm TIM Group, revolutionizing web application development for major investment banks and hedge funds through agile methodologies. Remarkably, he nurtured the Technology organization from its inception to a team of 49, maintaining exceptional standards of quality and resilience. Notably, TIM Group's recent acquisition by Mergermarket Group is a testament to the impactful work accomplished during his tenure.

After that he was CTO at the flash sales company Secretsales, implementing and improving methods for releasing new features several times a day as well as moving to Amazon Web Services to save £250,000 per year, driving over 50% of revenue from mobile devices using responsive design, and building the first successful flash sales loyalty program in the UK.

Transitioning to the position of VP of Technology at Osper, a pioneering payment card company, Douglas played a pivotal role in fostering financial literacy among kids and parents. Instrumental in achieving remarkable conversion and referral rates, he led a development team that deployed daily features, actively contributed to inventive solutions, and consistently enhanced tools and methodologies. For deeper insights into Osper's technological advancements, Douglas encouraged the exploration of the Osper Technology blog.

Driven by a passion for facilitating rapid growth and productivity enhancements in development teams, Douglas embraced shorter-term consulting roles to extend his expertise more broadly.

Last but not least! Douglas is offering one free certificate to one of our listeners, this certificate permits you to ask questions of software developers, system admins, designers, QA staff, and other technologists, check the full episode to understand more and contact him at

Connect with Douglas at: