After studying human sciences at Oxford University and then forging a career selling computer systems in the IT industry, Robin Osterley woke up one morning in his thirties and decided on a change of direction.
“It wasn’t any fun and I was fed up with selling stuff to people,” he tells Civil Society.
Osterley wanted a more fulfilling career and turned to one of his lifelong passions: music. A marketing job for an orchestra followed, followed shortly by a job as the managing director at a small classical music record label, which Osterley says “was always great fun, but was never going to be a long-term kind of thing”.
But it was through his work in music that he took on the role of chief executive at Making Music, a membership organisation for leisure-time music groups.
Osterley remained there for 16 years, followed by a short stint as CEO of Supporters Direct, an umbrella body for sports’ supporters’ groups, which he describes as “fascinating but extraordinarily stressful”.
Then, in 2015, along came Osterley’s current role at the Charity Retail Association (CRA). Thinking this would be his last full-time job, it looked like a good fit, enabling him to utilise his membership knowledge and understanding, as well as being in the charity world, which he found “really familiar” by this time, having worked alongside many in his previous roles.
“It seemed like a great opportunity,” he says, “and although I’d always been a fairly avid charity shopper, I knew nothing about retail.”
However, his knowledge and experience of membership organisations put him in good stead for entering the sector, which he describes warmly as “a wonderful world”.
CRA’s profile in the sector
Reflecting on his 10 years at CRA, Osterley says one highlight has been boosting the membership body’s profile within the charity sector. Although the organisation was “running a really great service for our members”, Osterley says, “I don’t think really we were connecting and communicating with the wider civil society agenda”.
“I’m quite proud of the way we opened up, not only to the rest of the civil society but also to the government, the powers that be generally,” he adds. “We became more visible to those people, so they suddenly started taking us seriously as a significant player.”
During Osterley’s tenure, CRA’s membership numbers have increased from around 400 members in 2015 to nearly 500 now, who operate over 9,000 outlets – around 85% of all UK charity shops.
The association’s membership and income numbers temporarily dipped when Covid struck, but Osterley felt proud of “the extent to which we were able to support our members during the pandemic”.
“That was really, obviously a critical moment,” he reflects. “There was a lot of fear around that time in two ways. First of all, there’s a fear they were never going to come out of it, and second, not survive and that whatever they did might be wrong.”
“The government was being quite vague about it, they couldn’t be specific to every single sector, so we had to work really hard to interpret what they were saying, to provide advice and guidance for our members.
“And I think we did that really well. That wasn’t just me, that was a real, massive team effort. Everybody’s jobs suddenly changed. We pivoted in all sorts of different directions as individuals and as an organisation, and we supported them really well.”
Previous negativity from commercial retailers
When Osterley first joined CRA, he noticed “not exactly hostility, but there was quite a lot of negativity about charity shops, particularly coming from commercial retailers”.
However, he says: “That’s really diminished, which is interesting. We don’t get anything like as much [now], and charity shops have become much more of a destination. There are loads of examples of people who only go into a town centre because there’s a charity shop.”
Now, much like the commercial retail sector, charity shops’ greatest challenges are stemming from rapidly rising costs such as the national insurance contributions (NICs) and National Living Wage increases, although Osterley is keen to add that the latter increase is ultimately positive.
“The big challenge they have at the moment is maintaining their profitability in the face of some really significant rising costs,” Osterley says.
“I think it’s better now than it was last year. They’ve adjusted and made the necessary moves to keep that profitability high. Whatever those moves might be will vary from charity to charity, but that’s clearly become a significant agenda item for the sector – ‘how do they keep these operations as profitable as they need to be?’”
Osterley adds that the reduction in the NIC threshold “really hurt” the charity retail sector, where many employees are part-time.
From 6 April 2025, the Employer National Insurance Secondary Threshold reduced from £9,100 to £5,000 per year, meaning employers will pay a 15% NIC rate on earnings above £5,000 per employee, rather than above £9,100, significantly increasing employment costs, disproportionately affecting part-time and lower-paid staff.
“The government had some really tough decisions to make, and we understand that, but it doesn’t seem right to us that the charity sector, which is doing a lot of the government’s work all the time, should be hit by this,” he says.
“There is a lot of concern that the government has the ability to hurt charities, but doesn’t seem to be quite balancing the ability to benefit them.”
AI potential
Despite these challenges, and amid charity shop closures from large charity retailers including Scope and Cancer Research UK over the last year, Osterley remains optimistic about the charity retail sector’s future.
“I don’t have any concerns about the future of shops,” he says. “I think they will continue. The landscape will continue to shift. And I think some of the trends we’ve been seeing towards higher standards and towards larger shops in particular will continue.
“And not only that, but I think charity retailers will be able to continue to leverage the online market in particular.”
Osterley and his colleagues have been assessing how best to use AI to benefit charity shops.
“We’ll be able to use artificial intelligence effectively to hone charity shops’ businesses, particularly when we’re talking about online stuff,” Osterley says, citing examples of a couple of CRA’s corporate members who are currently using AI to identify, describe and list donations in their online shops, widening the pool of potential customers and improving accessibility.
But on the online market generally, Osterley says: “None of that has really been possible for charity retailers in the same ways that it is for commercial retailers who have predictable stock; because charity retailers do not have [that], it's been a lot harder for them to leverage the online market.”
Looking to the future
Osterley advises his successor to stay up-to-date with the latest technology developments, including AI, but most importantly, to spend as much time as possible attending events and meeting charity retailers.
“That's where you get your inspiration,” he says. “They are so inspirational. They are so creative and resilient and caring about the sector and about the charities they represent, and so, so determined to make it work that you have to be made of stone not to be inspired.
“The best part of my job has always been attending shop openings or giving them awards, or going to conferences and talking to them.”
Although Osterley is not formally stepping down from his role until this December, he’s already looking forward to the next chapter in his life.
“It's exciting. It's a new phase of my life,” he says. “I'm really excited about it, but there's no question that I'm going to miss the joys of being involved in one of the most inspirational sectors that you can imagine.
“I've been really lucky in the last part of my career to be able to say that it is, it has continued to be, extremely enjoyable.”
He adds that he will miss CRA’s staff, who have doubled in number from five to 10 during his tenure.
“Most of them have been with us for quite a long time, and they really know what they're doing. They're really skilled at it. I'm going to miss them, and I'm going to miss our membership and their fantastic ability to innovate and their determination to succeed. I'm going to miss all of that a lot.”
As he approaches 70, Osterley is planning on slowing down but not stopping work entirely. He has been looking into part-time work, possibly in non-executive director positions, as an interim or a consultant.
But while his professional next step is unclear, as a singer in four choirs and a conductor of one, Osterley is definitely looking forward to being able to dedicate much more time to his music.
The Charity Retail Association is currently recruiting for Osterley's successor. See here for further details and the application pack. The closing date is 23 March 2026.
