• November 28, 2023
 CTT Group Director Bob Massey is awarded for his 40 years of service and innovation

CTT Group Director Bob Massey is awarded for his 40 years of service and innovation

When CTT Group recently hosted a roundtable for the Coventry & Warwickshire Chamber of Commerce, the last thing Director and co-founder Bob Massey expected was an ambush. “I’m normally the one standing at the front, ambushing somebody else,” Bob says, as he recounts the surprise presentations he’s led to celebrate significant events in the lives of his colleagues.

However, 2023 marks Bob’s 40th year working as an Independent Financial Advisor, something well-deserving of a special recognition award from the Director General of the British Chambers of Commerce, Shevaun Haviland.

A director of CTT Group since 2003, Bob specialises in the field of taxation and trusts. His 40 years’ experience as an IFA, and Trust and Estate Practitioner (TEP) have seen him change the face of estate planning and financial services alongside his CTT co-founder, Clive Ponder.

Bob’s early career success

The first place that Bob showcased his leadership skills was on the school Rugby pitch. “Rugby was important to me early on,” he recalls. “Captaining senior rugby from age 17, I was used to helping, guiding, and managing people who were older than me. I found my relationship with older clients, providing them with financial advice, came easy.”

After only seven years of embarking on his career as a financial advisor, Bob became the youngest ever branch manager of Legal and General, aged 29. He was eager to follow this success by carving out his own path. “The best decision was leaving Legal and General and setting up on my own,” he says. “I enjoyed teaching people, but I always wanted direct contact with clients. That’s what I enjoy and find most rewarding.”

Founding a new business

This ambition to engage more directly with clients saw Bob and his friend from rugby, Clive Ponder, establish their own company in 2003.

Their joint aim was to combine estate planning and financial support within one private practice, providing clients with a holistic service. Twenty years later, CTT Group is renowned for being a unique, multi-disciplinary network that serves both professional advisors and private clients.

“For professionals who don’t have internal expertise in the area, we provide that expertise,” Bob explains. “We go in and become a multi-disciplinary partner.”

CTT have added to their service offering with their own software that’s tailored to the sector: CTT Legacy. This innovation combines document drafting and management with a secure customer portal, providing a complete business solution for its users. And it’s something that is constantly being added to and updated. “The driving force behind CTT is improvement. There’s always another step ahead that improves your services, whether that’s B2B or B2C,” says Bob.

Leading by example

Whilst his job is to deliver professional advice, Bob’s approach is personal. “As an advisor, your strength is to be a listener first,” he reveals. “A client often doesn’t know what the problem is or what they need. We help clients identify that, then offer strategies to help them achieve balance.”

The satisfaction Bob gains in resolving the financial issues of his clients is just as rewarding as leading his team. “It’s a prize every time you watch someone you’ve brought on board succeed and seeing what they become,” he says. “You see people with hidden strengths who lack confidence; as a team leader, you give them that confidence.”

As well as inspiring his colleagues in the office, Bob also sets an impressive example outside of work. In June this year, he took on the incredible challenge of cycling the 500km from London to Paris, raising over £2,000 for the charity Care Leukaemia.

Keeping on track

A 40-year career is bound to present obstacles, but Bob sees these as chances to learn and grow. “It’s easy to get pushed in a different direction, personally and for the business. But if you see that happening you bring it back to what you intended – providing great service for clients and a great environment for the people you work with,” he says.

“I’ve learnt to make any decision in any circumstance for the right reason. You’re here for a good time, not long time,” he smiles, “so make decisions that are going to benefit your family, friends, and clients. Decide what journey you’re on and be consistent in what you do, then you’ll be happy.”

This article was submitted to be published by CTT Group as part of their advertising agreement with Today’s Wills and Probate. The views expressed in this article are those of the submitter and not those of Today’s Wills and Probate.

CTT Group


  CTT Group is an established Legal Services firm providing multi-disciplinary support for the UK’s Professional Adviser community. Their expertise spans multiple areas of Law, Estate Planning, Finance and Tax matters. CTT Group is recognised as a leading figure in the industry due to their wealth of experience and technical knowledge in the legal and financial sectors. CTT Group is made up of six areas: CTT Professional Services: A specialised knowledge hub designed for the Professional Adviser community and CTT Group members. The Professional Services team will provide you with a bespoke training and support package to suit any business. This includes the New entrants team, Training, Estate Planning Team, Professional Indemnity Insurance Service & the Resource Hub. CTT Tax and Trust: a premium support system for the Professional Adviser community, providing professional executor and Trustee services. They specialise in Estate Planning, Tax and Trust matters and have a wealth of knowledge and experience in delivering the right solutions for your clients. CTT Legacy Software: Ground-breaking legal software that will change how you work. Legacy was explicitly designed with you and your business in mind, so it will seamlessly align with your needs. It can also be tailored to suit your business needs, giving you complete control over your client journey. CTT Legal: Providing innovative and modern solutions to even the most complex legal problems. CTT Legal offer comprehensive Legal advice alongside CTT Law; an SRA-regulated law firm and strategic partner of CTT Group. This includes Residential and Commercial Conveyancing, Litigation, Document production, Client care, Professional Executor & Professional Executor. CTT Accountancy: A newly established Accountancy firm that will work in partnership with you and your business. CTT Accountancy is a practice of highly skilled and experienced accountants with expertise in trust matters, uniquely positioned to offer your clients a range of accounting services, whatever their needs. CTT Private Client: Offering individual professional advice to high-net-worth individuals with various financial situations. Their specialist team have a wealth of knowledge and will work with you to understand your requirements and provide bespoke advice. Click here for more information: https://ctt-group.co.uk/ Contact: CTT Group Tel: 01926 514 390 Email: enquiries@ctt-group.co.uk Address: CTT Group, Gables House 62 Kenilworth road Leamington Spa CV32 6JX