Trustee Matching Programmes

Trustee Matching Programmes

When I started this newsletter I often put in more trivial AI related items to keep things interesting, but as time has progressed, I’ve ended up losing some of these. So, by popular demand, today’s feature-of-the-hour is the Google ‘Try it on’ - if you haven’t given it a go yet, you now get a Try it On button when searching for clothing products, and it does a surprisingly good job of AI’ing an outfit onto a photo of you. It feels strange that it’s taken this long for it to appear… but the output is pretty convincing (we’re past the days of extra hands appearing), and my guess is that there must / should have been a lot of testing to ensure it resisted malicious deepfake-type uses (eg Donald Trump in a bikini), or more serious sexplotiation.

Today’s podcast is all around Trustee Matching programmes. Recently I got chatting with Ross McCulloch about Third Sector Lab’s Online Digital Trustee Matching events. They have a noble mission to get Digital onto every charity board agenda. I love initiatives like this, where they strive to develop a win-win situation where potential trustees get the chance to hone their leadership and decision-making skills, share some knowledge, and support a cause, whilst charities get access to talent, that otherwise they would be unable to afford. This ‘boutique-level’ volunteering is the type of thing which is making a real difference to the effectiveness of charities big and small.

Alongside Ross, I also speak with Elysha Paige who has been a doing a lot of work to shine a spotlight on charities that have live needs for digital expertise at a trustee level and ensure that opportunities like this are seen by a wider audience.

Stay Tuned for more insights in future episodes

If you’re new to the podcast - then definitely take a look back at some cracking episodes in the previous two seasons. Whilst there is a storyline flowing through the episodes, they work in any order, so don’t feel obliged to listen to them chronologically.

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If you’re keen for me to feature something going on in your charity, NFP or similar, please get in touch - and do comment on anything in here, or in the podcast that you like.

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About our host and guests

Ross McCulloch, Director Third Sector Lab

Ross McCulloch is a previous Big Issue Changemaker of the Year and founder of Third Sector Lab, supporting charities to deliver better digital services. Ross leads a team working with organisations on digital transformation, website design, campaigns, brand and beyond. Ross is also founder of Digital Trustees - supporting non-profits to find tech expertise for their board.

Elysha Paige, Director Radiate Hiring

Elysha is the Founder and Director of Radiate Hiring where she helps charities and purpose-led organisations hire tech teams and senior leaders. With a background spanning tech consulting, recruitment and charity leadership she now focuses on connecting talented and passionate people with organisations doing meaningful work.

Stuart McSkimming, Podcast Host

Stuart is a thought-leader in AI for charities and not-for-profits, and recognised in the 2025 AI100 list of the top 100 people shaping the future of AI in the UK. He is the founder of the sector-specific Technology & AI consultancy, Virtue Chain . He has over twenty years’ experience in NFP/Charity leadership roles, predominantly in the technology/digital and transformation space. He is an expert in getting the most from teams and focusing organisations on strategic goals to get the most from Technology & Digital. He is passionate about organisations focusing on inclusion and finding ways to attract a diverse mix of top talent into their teams. He has worked as a CIO for two organisations – Shelter and Royal British Legion, and also a variety of roles elsewhere. Stuart is extensively networked in the not-for-profit sector both in the UK, and internationally, and is the Vice Chair of top membership organisation, Charity IT Leaders. Stuart enjoys regular public speaking, and also has been known to do stand-up comedy gigs occasionally.

Virtue Chain builds the link between enthusiastic and talented technology teams, and organisation strategic goals. By focusing on people, strategy, governance and decision-making structures, Virtue Chain can help your charity get the right leadership approach across AI, Technology, Digital, Data, and transformation. We use maturity models, and partnering approaches to help trustees, CEO’s and exec leaders see the potential for technology in their organisation, and understand where to start in turning ideas into action.

Get in contact with [email protected] if you’d like to chat. Typically the conversation starts from either a trustee, CEO or CTO level.

In case its not obvious, views expressed are the personal views of the podcast host and guests and don’t necessarily represent those of any organisations they work with or for, either now or in the past.