10 Questions with: James Winter, Head of Finance at Paysend


In the second edition of the Rutherford Cross “10 questions with” series we hear from James Winter, Head of Finance at Paysend who discusses the importance of recognising the potential in every opportunity, how he has successfully transitioned across a range of industry sectors and the significance of transferable skills.

What does a typical day look like for you? 

There is no typical day at Paysend!  At some point or another in the chain, everything the business does will come across my desk which is part of what makes the role interesting.  It also makes it very challenging so a lot of my day will be spend discussing various operational or accounting items with my teams to ensure the business keeps going on a daily basis.  Then there will be regular reviews of the projects we have ongoing to ensure they keep moving forward as well as more tactical and strategic planning such as how the business can collaborate more effectively or how we can improve our margins.  This is all in between regular chats with my 2 year old who being tall enough to open doors can now just walk in when she feels like it!

What attracted you to join Paysend initially?

The chance to join a growing business in a growing sector.  Also the product itself; it is a great example of an innovation which makes life easier and simpler for those people who need this kind of service.

What defining career moments have there been for you so far and what career advice would you give yourself when you were younger if you could? 

The highlight so far would probably be my time on the Queensferry Crossing project and every time I drive over the bridge being able to think that I helped build this (figuratively at least).  As far as advice goes, it would be to recognise that you never know what could be the potential of an opportunity.  Just because something was not in your original plan does not mean it cannot become the new plan.

What does it take to be a successful leader?

One thing which I think is often overlooked is the ability to listen and remember there are at least 2 sides to every story so understanding different perspectives is key to making the right decisions.  I also think that a good leader will try and surround themselves with people who know more than they do.  Integrity is also important so that people know and trust what you stand for.

Many professionals we speak to feel that they are pigeon holed into a specific industry sector, throughout your career you have successfully transitioned across a range of industry sectors including Financial Services, Investments, Construction, Water Retailing and now Fintech – what is your secret?

No secret, it is simply about seeing the potential in the opportunities that come your way.  The core of what we do as finance professionals does not change so the key is to identify how you can apply your experience across different circumstance.  In my view, if someone has been successful in delivering a project or overcoming a challenge, it is very unlikely that their ability to do that would be confined to a certain industry or sector.

For those who might be interested in joining Paysend’s Finance team – what kind of person do you look for?

Someone who is willing to come in with an open mind.  Paysend is a fast growing and changing company so someone must be willing to learn but also adapt as we change and improve.

How would your colleagues describe you?

I would hope for something along the lines of “firm but fair” or “not a typical accountant”.  In every role I have done, I have always tried to position Finance as being there to help business departments to achieve their objectives but that this must be done in a well controlled and governed way.

If you could invite two people to a dinner party (living or deceased) who you choose and why?

Jeremy Clarkson and Jamie Oliver so I can talk about my two favourite topics; cars and food!

What is an interesting fact that people may not know about you?

I once did a video audition to become a presenter on Top Gear.  Needless to say I did not get the part!

If you weren’t in Finance, what would you be doing (for a career)? 

Formula 1 driver

For more information relating to the finance market in Scotland or if you would like to arrange a confidential conversation to discuss your career, please contact Georgina Millyard – [email protected]