James Wilson


I have always lived in Greenwich, apart from brief stints working abroad and at university.

After my Computer Science degree I worked in IT at various top 10 London law firms and set up Headstart in 2002 in my spare time.

Whilst working in law firms I further developed my technical skills and learned how to exceed the expectations of even the most demanding users; this experience strongly guided the way we do things here at Headstart.

I began running the business full time in 2006 and we have been growing steadily ever since.  Even though my days are busy, I’m happy that I work with a great team and great clients, and I’m very proud of the level of service we provide.

My main role is ensuring our clients and team are happy, whilst managing projects and growing the business.

I love keeping up-to-date with innovations in the tech industry; I read a lot of news and learn from my network of other MSP owners.

Outside of work I spend time with my wife and children; riding bikes, going to the countryside and playing Lego and, when time permits, I’m at the beach kitesurfing, riding the bowl in our new local skatepark, or on a snowy mountain somewhere.

Ashley Keshodia

Support Manager

With Headstart since: December 2007

Having struggled with IT issues in my early teens and with no one to help me (this is when most households had one computer with Windows 95, Word 97 with Clippy the unhelpful Paperclip companion, dial-up and Internet Explorer you installed from a CD!), I decided I needed to resolve my own IT problems.

From there I developed a keen interest in IT hardware, gaming and kept up to date with the latest and greatest kit; even if I couldn’t afford it myself!  I worked building and fixing PC’s for the now online-only company Maplin when I was 19 and went on to work for Headstart 4 years later and have been there ever since.

My interests include judo, boxing (watching, not partaking!) and, of course, spending time with my wife and young children.

Tim Winspear

Senior Engineer

With Headstart since: May 2018

I come from a background of corporate IT and have worked in small to medium business for over 20 years.

I am at home with fixing irritating niggly issues as well as designing corporate networks and everything in between.

I have a keen interest in the motorcycling world and run a Bemsee race team during the season.

I have a birthmark the shape of a 90’s PC, Monitor, Mouse and keyboard.

Rajan Regmi

IT Infrastructure Engineer

With Headstart since: April 2015

Over 20 years of experience in IT. Worked in Asia and Europe.

My first PC was based on Intel 8088 processor with 640K memory and Dual 5.25″ Floppy Disk.

I enjoy sports, travelling and of course IT.  I am married with two amazing kids, Rohan and Ryan.  When I am not at Headstart, I am accepting orders from them …

Elisa Vertue


With Headstart since: August 2009

Hi, I’m Elisa, I was born and grew up in Italy – near Milan – but I’ve been living in London for more than 10 years and worked alongside with James at Headstart since (he is the reason why I moved to London in the first place).  I mainly look after Headstart accounts and other office administration duties.

When I’m not working, I’m a proud mum of two young children and I love to spend time with my family and our dog; going to the park, cycling, walking in the country, skiing, swimming and much more.

I don’t like/can’t fix computer problems, but luckily I don’t have to; I have a great team of engineers around me.

Kate Hiles

Administrator/Credit Controller

With Headstart since: February 2015

I have over twenty years’ experience as a PA; in industries including Pharmaceuticals, Aerospace and Academia.

Sophisticated IT developments now allow me to achieve the perfect work/life balance; working remotely for Headstart IT Solutions whilst living with my family in the beautiful Lincolnshire Wolds.  When I’m not at work, I’m driving my two daughters to their various activities, walking our dog, doing boot camp and seeing friends.

Nathan Lamont

Infrastructure & Application Support

With Headstart since: April 2021

With 11 years working in the industry Nathan likes working in IT because he gets to help people and solve problems every day.  He thinks it is great to be able to make people’s lives that little bit easier, even if it’s just making their IT work as intended!  Nathan also enjoys technology that makes life more functional.  His enthusiasm for his tech hobby extends into his work at Headstart where he supports our clients and the rest of the tech team – he is happiest when especially troublesome problems arise.

Outside of tech, Nathan likes to pretend he can play football with his friends and trying to convince them to play Pokémon GO!

Andrew Parry

Support Engineer

With Headstart since: December 2021

I’ve always enjoyed creative hobbies and interests, making music and videos, graphic design, 3D modelling and 3D printing, video game modification and coding, all came back to the same core interest … Computers!

For the past decade prior to joining Headstart, I have supported IT in the education sector, managing the local network, workstations, mobile devices and general infrastructure.  This gave me experience fixing a wide range of issues, from Windows PCs, to Macs, cabling and even recording studios, as well as IT planning & procurement.  Alongside my technician duties, I also had some teaching responsibilities which instilled a passion in me for helping others.

Outside of work, when I am not on a computer, I enjoy football, walking, skiing, and accidentally hitting golf balls into the ceiling at the driving range.

Restored my faith in IT support

James, Ashley and the team at Headstart have put my faith back in to IT support. Their communication is clear and jargon free. They provide an excellent, efficient and professional service that I highly recommend.

Paula Lane
Oak Hill Community Nursery