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About Us

Hallsdale Insurance are a commercial insurance broker based in the Midlands but with clients throughout the UK. Our clients range from sole traders, SME’s and large multi-site corporate companies.

Our strapline – Your Business, Our Priority – is what we are all about and what we truly believe. We are passionate about our clients and their business and work closely with them to fully understand their evolving business and insurance requirements, to ensure we provide the very best level of insurance cover available on the market.

Our Values

It’s a people business.

Insurance is really a people business. People buy from people they like and trust, especially when it is something as important as insuring your business and employees.

Advice you can trust.

Hallsdale are committed to providing advice you can trust. We form long term relationships with our clients and provide innovative risk solutions. All of our conclusions and recommendations are purely given in your best interests, with your business at the forefront of everything that we do.

We strive to:

  • Recognise your individuality as a client and as a business.
  • Take total pride in what we do.
  • Form a long term trusted relationship with our clients.
  • Provide a first class service using top people and the latest technology.

Enjoy what we do!

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What our client’s say

“Hallsdale has been a great help to me while I have been off work due to an accident. Lewis Parker and Jon Tailby has been amazing every step of the way. They were always friendly and supportive with any enquiry I had. They was outstanding and I would 100% recommend them. Thank you for all the help you gave me in my time of need.”
Business Owner
Business Owner
“I was recommended Hallsdale Insurance by a fellow business owner who told me about how strong they were on the relationship side of things. That side is important to me, especially as our business evolved and changes. It was a great recommendation and I’m really pleased”.
Business Owner
Company Director

Expert Consultant

Meet our team of expert insurance brokers – with many years’ experience in the commercial insurance arena.

Click on each person to find out more about them!

1

Angela May

Managing Director
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2

Simon Drysdale

Director
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3

Lewis Parker Cert CII

Commercial Account Handler
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4

Nicky Masterson

Commercial Account Handler
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5

Jon Tailby

Commercial Account Handler
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Angela May

Managing Director

Having worked for Insurance Brokers since 1991, I have a high level of knowledge and experience with all classes of Commercial Insurance.

I lived and worked in Las Vegas for a few years in the late nineties and enjoyed the sunshine and bright lights.

I returned to insurance in 2002 and joined Hallsdale Insurance Brokers in April 2011. I had previously worked with the directors of Hallsdale for many years.

I love my job and take pride in advising my clients and meeting their insurance needs and going beyond.

I have two daughter who I am very close with. We like to socialise, shop and travel.

Simon Drysdale

Director

In 1988, I joined Keith R Drysdale Limited insurance brokers, based in Beaconsfield, becoming Company Secretary. The Company was eventually acquired by NFU Mutual and I took on the role of Broker Manager at the Country Mutual office in Corby.

After its merger with their Northampton Office I became the Manager of the newly combined offices. With the acquisition of Country Mutual by Towergate Risk Solutions in 2006, I became the Managing Director.

In late 2007 I became a founding Director of Hallsdale Insurance Brokers Limited, and remain a Director to this day. I have an unrelenting passion for insurance and I am as excited about it today as I was back in 1988!

I am a Past President of the Insurance Institute of Northampton. I have also contributed on several occasions to consumer related issues on BBC Radio Northampton. I have also served as the Chairperson of The Drayton Parish meeting.

I have always been a keen footballer and have coached at a junior level at my local club in Medbourne, Leicestershire, and although at heart I am a Chelsea FC supporter I have for several years been a season ticket holder at Leicester City.

I enjoy listening to music and in particular enjoy live performances, be it a festival (Yes I have been to Glastonbury!) or a local venue. Anything from Puccini to Motorhead, and I do dance as well Lindy Hop!

Lewis Parker Cert CII

Commercial Account Handler

I started my Insurance Broking career in in my home region of Dumfries and Galloway in 2004, and later relocated to Glasgow – and on to the East Midlands in 2010.   I joined the team at Hallsdale’s in 2016 as a Commercial Account Handler.

I have held my Certificate in Insurance for many years and look to progress to the Diploma in Insurance.  

I am the proud father of twin girls – which keeps me busy – and weekends are spent watching all their sporting activities.

Most of my spare time is spent running – and I take part in events around the country for Harborough Athletic Club.

 I also enjoy playing tennis and golf when time permits.  I am a keen supporter of Glasgow Rangers and Scotland.

Nicky Masterson

Commercial Account Handler

I have worked in insurance since the age of 17, starting my career with a local Insurance Brokers, dealing in personal lines insurance.

I then worked for Towergate Insurance Brokers for many years before joining Hallsdale Insurance Brokers in February 2021.   

I enjoy going to concerts and country fairs as well as competing at local dog shows with my lurcher.

Jon Tailby

Commercial Account Handler

I have worked in the insurance industry for over 24 years, starting initially in personal lines insurance, progressing to small medium enterprise and now tackle all aspects of business insurance based on a wide range of experience.

Working initially at Aviva I then took up employment at Country Mutual in 2003 with Simon and Angela, and then stayed on with Towergate Risk Solutions, until 2012 when they bought them.

Following this I moved to a local Broker based in Bedford as a Commercial Account Handler to look after Small Commercial Businesses and also Larger Account Executive Risks.

Following Covid I had a brief spell as a Farm Insurance Broker, where I was approached, in February 2022, and agreed to work with Hallsdales Insurance Brokers.  

In my spare time I enjoy following Liverpool Football club and I swim at least 3 times per week.  I love to travel, Croatia being a particular favourite. 

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