About Me

Douglas Squirrel


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. (TIM Group was recently acquired by Mergermarket Group, a nice validation of the work I and others did there.)

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.

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 CV.


For speaking, articles, books, and interviews, a photo of me is often helpful. Click the album for larger versions and more.

Squirrel leaning on cottage
Squirrel against wall
Squirrel full height

Guide Dogs for the Blind

My wife Lisa has been enormously aided by the tireless service and enthusiasm of her guide dogs. This is her current guide, Star:

Star, a yellow Lab/Golden cross dog

When people offer me gifts, I often suggest they donate to Guide Dogs instead. As a result my clients and I have raised over £2000 for this amazing organisation!


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

Open Source

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

  • A simple framework for microservices called combo, used at the Microservices Hackathons in London.
  • The Zen App, built on a dare, and perhaps the epitome of minimalist apps - basically just a blank screen. Still available for just 69p, though sales are a bit slow.
  • A Ruby-based project called Blindpages whose goal was to help blind people use poorly-built web sites that can't be interpreted by normal screenreaders. I briefly tried to commercialise this project, but was unable to achieve product-market fit. I still think there are opportunities here to help millions of visually-impaired computer users get more from the Web.
  • A Java framework for writing fluent behaviour-driven tests called Narrative. This was written at TIM Group (then youDevise) by Andy Parker with suggestions and fixes from many colleagues. I think my main contribution (other than hiring Andy) was to write the intro web page.
  • A simple Java recipe-management program I wrote in 2002, called LargoRecipes. Much better recipe-management systems now exist, such as Paprika, so I am no longer working on this project. LargoRecipes could convert recipes from older text formats to a proposed XML standard, RecipeML; I maintain an archive of RecipeML recipes that I converted in this way.

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.