The Team


Sean O’Keeffe | Managing Director

Sean is an experienced manager with a military background that saw him serve in Northern Ireland, Iraq and Afghanistan as a surveillance and reconnaissance specialist. Sean left the Army in 2006 and then went on to join Aegis Defence Services for 5 years on a Department of Defence contract in Baghdad as head of IT and Communications. As the Managing Director of The-Training-Wing, Sean has guided the company from a concept to winners of the Chamber of Commerce’s ‘Best Start Up’ business and also as a finalist at the ‘Audi’ business awards 2013. Sean enjoys fitness, horse racing and reading.

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Jordan Wylie | Director

Having spent almost 10 years in the British Army with service in Iraq and Northern Ireland, Jordan has since gained valuable experience as maritime security specialist, having completed over 100 high risk transits worldwide and being an official security advisor to the IMO, he has extensive operational and training experience with some of the world’s largest shipping companies. Jordan has recently spent two years as a maritime security operations manager with a leading international security company as well as becoming a Department for Transport (DfT) and Maritime & Coastguard Agency (MCA) instructor.

Jordan has developed his industry knowledge significantly by studying for a BA (Hons) in Security & Risk Management with the University of Leicester. At present Jordan is employed as the Director of Operations at The-Training-Wing and is responsible for business development and overseeing all training operations that the company upholds. He has also recently qualified as an International Standards Verifier for Pearson & Edexcel for security training programmes overseas.

Jordan is an avid Blackpool FC fan and enjoys travel, reading, networking (business) and most sports.

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Michael Preston | UK Operations Director

Mike is a highly experienced training instructor and manager with 16 years military service which predominately involved the provision of specialist weapons, firearms and tactics training for armoured and dismounted units worldwide, including in Iraq and Afghanistan. Mike has recently dedicated significant personal time to studying for a level 7 Diploma in Leadership and Management which has benefited the company significantly in period of rapid growth and development, he has also been instrumental in assisting the company in gaining our ISO9001 accreditation.

At present Mike is the UK Operations Director and is responsible for managing a team that coordinates all training courses that take place within the UK. Mike is married with 3 children and is another passionate follower of Blackpool FC.

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Stacy Ashton

Stacy Ashton | UK Training Manager

Stacy Ashton is the UK Training Manager and senior medical advisor with a background as a Combat Medical Technician (Class 1) in the Royal Army Medical Corps, she served with distinction in Kosovo, Bosnia, Iraq and Afghanistan. Stacy recently left HM Forces after nearly 14 years’ service, leaving as a Senior Non Commissioned Officer and gaining a Commander in Chiefs commendation for outstanding service to Queen and country.

Stacy has recently deployed back to Iraq as a medical training advisor for The-Training-Wing to provide consultancy services to some of our large security clients such as Aegis Defence Service and Triskel Consulting.

Stacy enjoys keeping fit and spending time with her family, especially her son Archie.


Darren Gray | Training Coordinator

Darren is an experienced security and training consultant who joined TTW on a full time basis in December 2013. Darren brings a wealth of knowledge gained from serving 22 years service in British Army, predominately as a forward observer with the Royal Artillery.

Darren is an award winning photographer with an eye for detail and a passion for surveillance. He has been brought in to the company to act as a point of contact for students wishing to book on courses and to assist service leavers with making a smooth transition from military life to the challenges faced within the civilian sector. Darren has recently studied for his Diploma in Security Management and has spent the last 4 years prior to joining TTW carrying out tasks in the specialist fields of Asset Protection, Close Protection and Security Management.

Darren has been married to Joanne for 20 years and his hobbies include photography and shooting.


Michelle | Administration Team


Michelle  is TTWs UK Assistant. Michelles role is to process students upon completion of training. Originally from the Midlands she moved to the Tidworth area with her family and has since become an integral part of the TTW team.