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Meet the Team

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David Oakley

David Oakley

Marketing & Strategy

What is my job role?

I lead the commercial team, which means it’s my job to help the team help schools give life-changing expedition experiences to as many young people as possible.

Why Outlook?

It’s my Ikigai - where I can do a job that I love, that I am [reasonably] good at, that I can get paid for, and that the world needs.

What is an experience that has helped shaped me?

2 years living in The Gambia in my mid-twenties. I grew up, and dodged malaria.

Where is my favourite place in the world?

Tricky. Would be easy to say The Gambia, but instead I will say Fez in Morocco - literally a maze, a blend of cultures, sensory experiences and wonderful, clever people.

If I could sit next to anyone on an aeroplane, who would it be?

Iggy Pop
Rebecca Edwards

Rebecca Edwards

Sales Operations Manager

What is my job role?

Sales Operations Manager

Why Outlook?

Outlook still provides genuine, student led, immersive adventure travel experiences for young people

What is an experience that has helped shaped me?

Journeying overland through Asia and Europe, from Hong Kong to the UK

Where is my favourite place in the world?

Palawan, Philippines

If I could sit next to anyone on an aeroplane, who would it be?

Karl Pilkington
Hugh (Bug) Wrightson

Hugh (Bug) Wrightson

Regional Associate

What is my job role?

Beginning as a freelance Expedition Leader I've taken on a wide range of other responsibilities within Outlook and am now involved in sales, leader training and development, the pre-expedition journey for students, risk assessment, and logistics

Why Outlook?

Personal Development of our students; that's it, that's all

What is an experience that has helped shaped me?

Qualifying as an operational Search Dog handler.

Where is my favourite place in the world?

Indian Himalaya as I love the food, the people, and the scenery

If I could sit next to anyone on an aeroplane, who would it be?

Anyone who understands Search Dogs
Jen Reynolds

Jen Reynolds

Operations Manager

What is my job role?

I manage the planning team and am responsible for the risk and safety management of the business to ensure we deliver high-quality, safe, and successful expedition programmes for our young people

Why Outlook?

Because I genuinely believe in the transformational effects these experiences have on the young people who travel with us. I have witnessed first-hand the real-time learning the students go through and the long-term benefits that they can take away from the experience. Also- there is nothing better than working with a bunch of like-minded people who are all driven by the same purpose

What is an experience that has helped shaped me?

Every expedition or overseas experience I have ever had. Not only have they allowed me to visit some of the world's most beautiful places, but they have also taught me a great many things about myself- building essential life skills like resilience, patience, confidence and an understanding and appreciation of other cultures

Where is my favourite place in the world?

Anywhere my children are. Preferably in the hills with our walking boots on and a nice flask of hot chocolate!

If I could sit next to anyone on an aeroplane, who would it be?

My dad. Chatting about all the places we have yet to visit together
Stacy Shepherd

Stacy Shepherd

Programme Manager

What is my job role?

Programme Manager

Why Outlook?

I thrive in a team of dynamic, well-traveled individuals who believe in the adventures we offer. Our collective experiences give us a unique insight into the transformative power of youth-led expeditions. That’s why we’re committed to going above and beyond to ensure every school and student has an unforgettable and life-changing journey

What is an experience that has helped shaped me?

At 18, I faced an unexpected challenge when I broke my hip during my time in the Army, resulting in a medical discharge and a complete upheaval of my life plans. Recovering from this experience required immense resilience and courage—qualities that have supported me through many adventures around the world since

Where is my favourite place in the world?

An empty beach

If I could sit next to anyone on an aeroplane, who would it be?

Ben Fogle
Janet Serralha

Janet Serralha

Finance Coordinator

What is my job role?

I handle the financial operations, including bookkeeping, VAT returns, and financial reporting, ensuring the company’s accounts are accurate and up-to-date

Why Outlook?

Outlook values teamwork and growth while creating life-changing experiences for young people. I love being part of a mission that genuinely makes a difference

What is an experience that has helped shaped me?

Relocating from South Africa to the UK. The process of starting fresh in a new country taught me resilience, adaptability, and the importance of stepping out of my comfort zone

Where is my favourite place in the world?

Sitting in my kitchen, baking with my son Carl, and creating happy memories

If I could sit next to anyone on an aeroplane, who would it be?

My late mother. I’d love to share my journey with her, as she always inspired me to aim higher
Hanna Dixon

Hanna Dixon

Operational Resources Manager

What is my job role?

Operational Resources Manager

Why Outlook?

The combination of working with adventure, the outdoors and travelling – and providing all of this to young people

What is an experience that has helped shaped me?

Travelling on my own for the first time around Australia. I realised the power of experiencing new things, talking to new people and knowing that I could do all of this myself. This is the super power I hope that Outlook will instil in young people travelling with us

Where is my favourite place in the world?

On a mountain path in The Lake District with my husband and daughter

If I could sit next to anyone on an aeroplane, who would it be?

Someone who doesn’t snore or Thor Heyerdahl telling me all about his weird and wonderful theories
Julia Entwistle

Julia Entwistle

School Expedition Consultant

What is my job role?

School Expedition Consultant

Why Outlook?

I want to be a part of providing young people with transformative opportunities to grow into resilient, confident global citizens. In an increasingly isolationist world, I’m passionate about helping students broaden their horizons, understand diverse cultures, and develop the skills they’ll need to navigate and shape the future

What is an experience that has helped shaped me?

There are many but one is definitely having our campsite torn apart in a huge storm on the side of an active volcano in Russia and another would be becoming a parent. Similar in some ways

Where is my favourite place in the world?

Always a tough one but probably Alaska. I just love everything winter and snow and going to Alaska was a place I'd dreamt about going since I was 6 years old

If I could sit next to anyone on an aeroplane, who would it be?

No one. Can't beat a row to myself so I can stretch out and read
Emily Stephenson

Emily Stephenson

School Expedition Consultant

What is my job role?

I’m one of the School Consultants, which means I help schools give as many young people as possible the chance to go on life-changing expeditions

Why Outlook?

Honestly, who wouldn’t love a job where you get to chat with travel-mad teachers and schools all week, helping to bring amazing adventures to young people? It’s the best

What is an experience that has helped shaped me?

Growing up, I was lucky enough to travel the world and explore some incredible places. Those adventures taught me how powerful travel and exploration can be, and I want to help other young people experience that too

Where is my favourite place in the world?

That’s a hard one! After spending so much time away from the UK, I’d say Keswick in the Lake District is a cozy favourite. But if I had to pick somewhere further afield, Malaysia is just amazing—I’d go back in a heartbeat

If I could sit next to anyone on an aeroplane, who would it be?

Steve Irwin, hands down. What a legend!
Beth Turner

Beth Turner

Destination Planning Manager

What is my job role?

Destination Planning Manager

Why Outlook?

One of the few travel experiences for young people which mirrors what travelling is actually like and allows young people to have an active role in their expeditions.

What is an experience that has helped shaped me?

Deciding to pack it all in and spend our savings travelling the world until our money ran out with a bucket list and no concreate plans…….in our mid 30s!

Where is my favourite place in the world?

Tough one….Slovenia, New Zealand, Koh Kood or Don Khon (couldn’t chose just one!)

If I could sit next to anyone on an aeroplane, who would it be?

Someone local to where I am travelling to….the best source of knowledge for all travellers
Robert Fox

Robert Fox

Marketing Activation Coordinator

What is my job role?

Marketing Activation Coordinator

Why Outlook?

Jealousy mainly. When I first saw the wonderful options for expeditions that Outlook offers, I really wished I’d had the chance at my school! At least by tyring to encourage others to take advantage of these life changing opportunities, I can convince myself I’m cool about the fact my school didn’t offer them. Makes sense when you think about it.

What is an experience that has helped shaped me?

Walking the battlefields of the Somme on my own and getting my first glimpse of the Thiepval Memorial over the horizon.

Where is my favourite place in the world?

Dunkeld in Perthshire. Failing that, anywhere around the Mediterranean.

If I could sit next to anyone on an aeroplane, who would it be?

Richard Burton, though it would have to have been when you could still smoke on flights to get the best out of him.

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