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Douglas Squirrel

Growing Productive Teams Since 2004

ds@douglassquirrel.com • +44 (0) 777 3795 491 • LinkedInSchedule

"Squirrel is an exceptionally talented CTO who helped revolutionise the SecretSales’ Technology function. He hired and integrated a new team and implemented future-proof practises that have enabled the efficiency and quality of the Technology team’s output to continuously improve. He is an accomplished and inspiring manager and was a well respected Senior Team Member during his time with us at SecretSales. He has cultivated a finely-tuned, self-sufficient Technology function, which we are very grateful for." - Nish Kukadia, founder, Secretsales
"Squirrel has contributed immeasurably to our company’s success during his ten years as our CTO. Squirrel built a 50-strong Technology team which has fuelled our growth and earned us recognition as a leading proponent of best-practice software development. He established the technical, management, and recruitment processes that have supported our operations and on-going growth. He has shown himself to be a gifted technologist, a strong manager, a good contributor to business discussions, and an eloquent company representative on technical issues. " - Rich Koppel, founder, TIM Group
"When Squirrel began working with us, the engineering team was full of talented and committed developers who lacked leadership and confidence. He helped to transform them into an energised, highly-focused team who now deliver high-quality product better and faster than I could have imagined." - Paul Joyce, founder, Geckoboard

This page is all about my professional and personal pursuits:

CTO - Fixing and Growing Software Development Teams

I fix software development teams that aren't working at their best - delivering poorly or not at all, lacking leadership, or struggling to recruit. It typically takes me three to nine months to address these issues and get the team on track to deliver on company goals. By the time I finish, I've recruited or trained a high-performing tech leader and a skilled team that's ready to keep delivering.

I've done this repeatedly over a fifteen-year career in software development. Among others, the founders I've worked with at TIM Group (investment banking, backed by Commonwealth Capital), Secretsales (e-commerce, Doughty Hanson), and Osper (debit cards for kids, Index Ventures) rave about what I've accomplished.

I'm open to all types of engagement, from full-time permanent to interim CTO to part-time consulting. I am very happy to travel - but not relocate - to most locations in Britain, the Continent, and the US (I am a dual US/UK citizen). I'm also interested in opportunities to advise startup founders and tech leaders, as a formal advisor or an occasional mentor. Further, I'm often available to speak at events for investors or startup founders on topics like tech hiring or building a product roadmap.

See my case studies page for examples of my work with a variety of companies.

Advising Startups

I enjoy providing advice and help to startups of all kinds, in industries from energy trading to dog grooming. I can do this in several ways:

Pre-Seed Stage: Breakfast with Squirrel

I regularly have brief meetings - often, but not always, at breakfast! - with individual startup founders to answer questions and provide informal advice. My breakfast partners are usually not yet funded or just raising a seed round, and sometimes have nothing more than a clever idea. These sessions are free and book up fast, so get in touch soon - for early risers, book online for an 0800 breakfast in London, or email me to find another time. See my notes on startup advice for more information (and maybe some answers to your burning questions!)

Seed/Accelerator Stage: Mentoring

At any time, I usually have a couple of startups that I work with as a mentor. This normally means that I spend 2-4 hours each month helping in various ways - interviewing candidates, answering questions from the founder or technology team, reviewing code or development processes, helping prepare for due diligence, and more. Typically, after a brief trial to check we work well together, we cement this relationship with a mentoring agreement granting me a very small equity stake in exchange for regular advice. I often find startups to work with through accelerators like TechStars, Entrepreneur First, or Startupbootcamp, but am open to hearing from anyone interested in mentoring of this kind.

Any Stage: Clarity Call

I am experimenting with paid calls through a service called Clarity - see my profile. The idea is that you get on a video call with me, billed by the minute, and we talk through startup tech issues - how to recruit, why your tech lead isn't leading, what the barriers are to improved developer productivity, or anything else that's on your mind. I should be able to help you quickly and give you significant value without a full CTO engagement. Let's try this out together - get in touch to arrange a call soon!

Any Stage: CTO Engagement

Of course, if you'd like to go beyond advice, you are welcome to arrange a consulting or permanent engagement with me, as described above. Typically, I book a specified number of days per week for a fixed period, e.g. 3, 6, or 9 months. Depending on availability, I can also arrange to help on a more flexible "retainer" model, where I commit to a small number of hours or days per month that you can use how and when you need them, if that suits your needs better than a full- or part-time commitment.

Courses and Talks

I speak and train regularly on software development and management topics. For example, recently I gave two conference talks based on experiences at Geckoboard - watch them below if you are interested.

I can offer talks or short courses on a number of topics - a sampling appears below. Please let me know if you would like me to speak at a conference or meetup, or if you would like me to deliver a custom half- or full-day course for your company or organisation.

Research and Open Source

I get little time for theorising but do manage to keep my hand in with several areas of research.

Action Science

Inspired by Benjamin Mitchell and Jeffrey Fredrick, I'm interested in how the "Action Science" management theories of Chris Argyris can be applied to the problems faced by development teams. I make videos about Action Science techniques with Jeffrey Fredrick, participate regularly in the London Action Science Meetup, and strive to apply "Model II" principles in my daily work:

You can read more, including early drafts of my book on how to use these techniques, on my page on Action Science.

Open Source

I get few opportunities to write code in my current job, so I try to keep my skills up by working on one or two programming projects in my spare time. These have included:


In the 1990s I studied mathematics as a student at Reed College and the University of California at Berkeley. During that time I:

Personal Matters

I live in the hamlet of Frogholt, near Folkestone, in a 600-year-old cottage. You can see pictures of the cottage if you are interested.

Possession of the Doyle Owl is the pinnacle of achievement for all honourable Reed College students. I have a collection of Doyle Owl photos and documents accumulated when I was part of a team of students in possession of the fabled Owl.

Biography and CV

I fix software teams that aren't working at their best - delivering poorly or not at all, lacking leadership, or struggling to recruit. It typically takes me three to nine months to address these issues and get the team on track to deliver on company goals. By the time I finish, I've recruited or trained a high-performing tech leader and a skilled team that's ready to keep delivering.

I started my leadership career as CTO of financial software firm TIM Group, using agile methods to build web applications for the world's largest investment banks and hedge funds and building the Technology organisation from nothing to 49 people while retaining unusually high levels of quality and resilience.

After that I 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 programme in the UK. You can read more in a recent RealBusiness article about the role of technology in achieving profitability and growth at Secretsales.

Next, I took on the role of VP Technology at inspirational payment-card firm Osper, which is helping kids and parents learn about money management together using a prepaid debit card and mobile app. Osper has achieved impressive conversion and referral rates leading to extraordinary growth - hundreds of signups per week with minimal marketing - thanks in no small part to a development team that deploys new features daily, participates fully in inventing solutions, and continuously improves its own tools and methods. You can read the Osper Technology blog for more news about the growth and development of the Technology group at Osper.

Finally, after repeatedly helping development teams grow quickly and make rapid improvements in their productivity, I decided to take up shorter-term consulting roles to provide this assistance more broadly.

You can find an even more detailed history in my curriculum vitae (CV in PDF format).

Squirrel Squared Limited (company number 07008780) is a company registered in England and Wales. The company, along with Squirrel, Lisa, Paige, and Star, resides at Old Kent Cottage, Frogholt, CT18 8AT. Come and visit anytime!