One Step at a Time: Our Digital Transformation Journey

By Jamie Trout – Head of Digital at Simon Community Scotland

Putting people, purpose, and inclusion at the heart of digital transformation – and what we’ve learned along the way.  

Where it all started

When I joined Simon Community Scotland, I wasn’t aiming to “digitally transform” anything – I just wanted things to work better for our teams and, most importantly, the people we support.

At the time, digital was seen as a “nice-to-have” for the people we support. Our teams were deeply committed, but the tools around them hadn’t kept pace with emerging digital technologies. That made sense – the focus had rightly been on the urgent needs of people experiencing homelessness.

Gradually, we saw how digital had the potential to enhance our work. It’s been a journey of learning, missteps, small wins, and meaningful progress. Digital is now central to how we work – not to follow the latest trends, but to help us work in more connected, informed, and responsive ways.

It’s never been just about tech – it’s about people, culture, and mindset.

Building a shared vision

Our first step was defining what digital meant for us. We developed a strategy rooted in the realities of homelessness and shaped by our values.
Through organisation-wide engagement, two clear workstreams emerged:

• Inclusion, ensuring digital is accessible and meaningful for everyone, and;
• Evolution, using technology to refine – and sometimes reimagine – our systems, processes and ways of working.

We were fortunate to have strong support from our leadership team and board from the outset. We established the Digital Strategy Committee – a Board subcommittee that supported and guided our work by providing governance, managing risk, encouraging innovation, and ensuring accountability. Their early buy-in was a significant milestone in our digital transformation journey.

Putting people before platforms

One of the biggest lessons I’ve learned is that digital change only works when people are involved early, openly, and with genuine curiosity. The people using systems every day know what works – and what doesn’t – and their insights are essential in shaping meaningful change.

The key to unlocking those insights is empathy: You’re often stepping into someone else’s world – their tools, their processes, their pressures. Take the time to really understand their challenges. The more authentic your insight, the more relevant and lasting your solutions will be. That’s where real digital progress begins.

Making change that matters

We looked closely at the systems people rely on every day, including recruitment, HR, fundraising, volunteer management, payroll, and learning and development. Each of these areas became the focus of a distinct and significant change project. We worked with teams to explore what could be improved. This led to major changes in processes and technology across all of these areas.

Developing integrations between our key systems reduced duplication, streamlined workflows, and improved access to information. This helped to save time and resources while enabling more joined-up, transparent working across the organisation.

We reimagined the Simon Community Scotland website to make it more inclusive, easier to navigate, and more meaningful for those engaging with our work. Moving to Google Workspace wasn’t just an IT upgrade – it transformed how we share knowledge, make decisions, and collaborate. Change is rarely smooth. We didn’t always get it right – but we stayed open, kept listening and adapting.

Growing capacity with creativity

We looked for practical, sustainable ways to build digital capacity. Through the Third Sector Lab’s Digital Trustee’s Programme we brought a digital trustee onto our board to boost strategic oversight, and I took part in SCVO’s Digital Senior Leaders Programme to strengthen our leadership approach.

We also capitalised on opportunities to bring in students and graduates – adding fresh energy and insight. And we stayed persistent in seeking funding to help us keep moving forward.

Co-design: shaped by lived experience

Some of our most meaningful work has come from co-creating digital tools with the people we support. A standout example is the award-winning By My Side app, developed with our inspiring Harm Reduction Team in partnership with the brilliant team at AND Digital. Because people with lived experience were involved throughout, the app reflects real needs. One feature came directly from a suggestion by someone using our services – a powerful reminder that lived experience brings essential insight. Their input ensures our tools are not only inclusive and supportive but useful and relevant.

Turning insight into action

A theme within our digital strategy was to prioritise and enable data-informed decision-making. It’s still a work in progress, but we’ve started using tools like Looker and Google Analytics to help us visualise the data that matters, spot trends and better understand user behaviour and platform performance.

By leveraging analytics data from our website, social media channels, fundraising, HR, and recruitment systems, we’re creating an accessible, cohesive view of what’s working well across the organisation – and where there’s room to improve. It’s a mindshift as much as a technical one and it echoes this thought-provoking quote:

“Without data, you’re just another person with an opinion.”

 – W. Edwards Deming

Putting inclusion at the centre

The growing digitalisation of society risks leaving people behind – especially those already facing disadvantages such as homelessness. Without care, digital transformation can widen inequalities instead of closing them.

To help prevent that for the people we support, we launched Get Digital Scotland – a programme providing devices, data, and support to help people affected by homelessness build the skills and confidence to participate fully in the digital world. You can read more about this in my previous blog post: Embedding Digital Support Since 2017.

What began as a small local pilot has grown into a national flagship digital inclusion programme within Scotland’s homelessness sector. We’ve trained over 500 support workers in digital inclusion (with our incredible partners at Mhor Collective) and as a result staff have supported more than 3,000 people get online – many for the first time.

The impact has been life-changing – enabling people to reconnect with loved ones, manage finances, access services, find work, and sustain a home.

One participant shared, “I feel part of society” – a powerful reflection that inspired the title of our latest impact report, I Feel Part of Society. 

What I’d tell others

If you’re thinking about digital change in a charity, here’s what I have learned:

• Start with people – Technology only works when it solves the right problems. People closest to the work are best placed to define those problems and co-create solutions.
• Stay true to your values – Let your purpose guide your decisions, not the tech itself.
• Get buy-in from leadership – It gives the work legitimacy, momentum, resources, and decision-making power – and signals digital change is a shared priority.
• Change takes time – Celebrate the wins and learn from the bumps in the road.
• Prioritise inclusion – Digital should work for everyone – not just the confident or connected few.
• Be curious and keep learning – Digital technology changes and evolves just as quickly as the needs of the people, teams and organisations using it. The only way to keep up is to stay curious, keep asking questions, and continue learning. This helps to shape solutions that truly work and keep improving over time.

A journey, not a destination

Digital transformation at Simon Community Scotland has never been about reaching the finish line. The goalposts will always keep moving as technology evolves – just when we think we’ve caught up, along comes AI suggesting it can do it faster (but still struggles to write a decent funding bid).

It’s an ongoing journey – shaped by collaboration, guided by our values, and centred by lived experience. There’s always more to learn, more to try, and more ways to improve how we support people experiencing homelessness. That’s what keeps us moving forward – one step at a time.

• This blog was crafted with human insight and AI assistance – blame me for the ideas, and the AI for any weird bits.
• Want to learn more about our approach or share your experience? We’d love to connect: jamie.trout@simonscotland.org