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Meet the Directors

The Directors

Having started the company, Robert Massie has now strategically enhanced the senior management of the organisation with key members specialising in specific areas of the business.

Richard Field OBE


Approached by Robert Massie to assist Highlander as a business consultant, Richard became chairman two years later in 1997.

Richard has a passion for individual, team and organisational growth and development.  His love of leadership and learning are the threads that link many of his past and current appointments.

Highlander benefits greatly from the expert advice and coaching that Richard delivers. His wealth of experience and knowledge will be key to further success at Highlander Business Solutions.

Robert Massie

Chief Executive

Robert formed Highlander in 1995 to serve local SME´s and Universities with computer systems and solutions.

Whilst his birthplace is Aberdeen, Robert chose to settle in South Yorkshire and has not looked back since. His passion for Highlander and Sheffield has led to Robert being invited to become an Ambassador for Sheffield by Sheffield First for Investment.

Robert is an active Chief Executive who enjoys working ‘in´ as well as ‘on´ the business. He thrives on the variety and diversity that comes from managing a fast growing and successful I.T. & Telecoms Company.

Steve Brown

Managing Director

Joining Highlander in February 2001, Steve has operated in a number of roles within the organisation – starting as Field Sales Executive before progressing to Sales Manager, General Manager, Commercial Director and now Managing Director.

After leaving College Steve was a professional footballer for two years before injury curtailed his career and he went back to education, graduating from Sheffield Hallam University in 1998. Steve then worked for two years in Cardiff as a Finance Manager with a leading retailer before moving back to Sheffield.

Karrie Massie


Karrie joined Highlander in February 2002 as Company Secretary and Director.

Qualifying as a Dental Hygienist from Charles Clifford Hospital in 1986, Karrie had commanded a number of diverse roles within the private dental industry.

Karrie joining Highlander in 2002 coincided with the exciting move to our premises at Sheffield Airport Business Park. Since her appointment Karrie has completely re-structured all company Health & Safety, Employment Law and other legislative procedures and still maintains control over these whilst now also spending more time in a more customer facing role.

Chris Muscroft

Commercial Director

Chris joined Highlander in April 2003 following a successful career in I.T Account Management.

Having started his career at Sheffield Newspapers, Chris left to pursue a sales role for a local I.T. supplier, providing network solutions for small businesses in the South Yorkshire area.

After two rewarding years, Chris left to further develop his technical and account management skills. His remit was to design solutions aimed at reducing costs, enabling growth and increasing profitability for the company´s client base.

Chris was also responsible for the company´s Microsoft licensing arm for the UK. Chris´ goal for Highlander is to utilise his experience when developing complex and business lead I.T. projects for new and existing clients. He is also developing a team of professional Account Managers to provide the highest level of I.T. service available in the SME market place.

John Akings

Technical Director

Joining Highlander in March 2001 as a Field Engineer, John has progressed through the roles of Technical Resource & Project Manager to Technical Director.

Born in Doncaster, John joined the Royal Air Force after leaving school in 1982. Working in Logistics for 14 years responsible for ensuring equipment was available all around the world to keep the fleet flying. This included tours in UK, Germany, Ascension Island and the Falkland Islands before pursuing his hobby of IT from 1996.

John’s vast experience on service delivery has ensured a continual rise in service performance since his appointment. Continuation in these performance levels is a key focus area for future initiatives and developments in the provision of technical resource and expertise to our clients.

Ryan Conolly


Ryan joined Highlander as a Commercial Account Manager in August 2007. Since then Ryan progressed to Sales Manager and then appointed a Director in November 2015.

After leaving college Ryan lived in Florida after taking up the offer of a Football Scholarship, spending most of his time playing and then coaching at the local High Schools. Following his stint in Florida Ryan then returned back to Sheffield where he then studied Business and Finance at Sheffield Hallam University.

Following University Ryan then worked for Norwich Union and HSBC before moving into I.T. with a UK wide recruitment consultancy. Today Ryan plays an important role at Highlander in developing the small business managed services team.

Lee Wragg


Lee joined Highlander in 2004 and started as the 1st Highlander Direct Account Manager. Since then, Lee has excelled in several roles at Highlander, including Senior Account Manager & Head of Sales.

Lee’s success was rewarded when he was appointed to the board of directors in November 2015.

On leaving school Lee studied business at college before spending 10 years with Morrison’s where he rose the ranks to department manager before taking the fresh new challenge of I.T. and sales. Lee has achieved sales success with a global I.T. supplier and also spent time working for a small I.T. provider before moving to Highlander.

Today Lee plays a key part in the development and implementation of Highlanders sales strategy with the key focus on Major accounts.