Classy Creativity: a Chat with Cheddar Creative

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It takes guts to find the courage to start from scratch. It can go either way. Too many have fallen under the weight of poor planning, but those who have succeeded give us hope that we can do the same. Cheddar Creative is a prime example of that.

In just three years, Cheddar Creative has grown to become a promising and highly ambitious agency, able to bring home more than a few successes – including being shortlisted as the Best Agency to Work for in Annual 2020. Refusing to scalp clients off their previous employers, Creative Director Cassie Bendall and Strategy Director Richard Wood have built an entire new business from the ashes of their old experiences – only to find out that some of their old clients were more than keen to work with them again, thanks to a partnership that went above the business-as-usual and turned into something more human. And though Rich has come aboard only after the foundation of Cheddar Creative, we can see why he can confidently call it home.

For this Company Spotlight, we are learning more about the story of an ambitious creative agency that can only keep producing incredible work, and we honestly can't wait to see more of that.


Image credit: CliQQ Studios

How was your company born and where are you based?

As with most new businesses, Suffolk-based Cheddar Creative was born out of frustration and the determined belief that “we can do better”. The founders had both worked in the digital marketing space for several years, in Suffolk, London and overseas, and had become jaded by the seemingly ineffective, copycat tactics employed by these so-called “creative” agencies. That, coupled with a growing desire to do their own thing, lead with a more design-driven approach, take bigger risks and have no one else to blame if things don’t pan out as intended, led to Creative Director Cassie Bendall founding Cheddar at the end of 2017, with Strategy Director Richard Wood coming aboard shortly after.

What was the biggest challenge for the growth of your company?

The biggest challenge to growing the business, or even getting started really, was attracting potential clients, then charging our true value (gradually reducing the level of over-servicing until we became profitable – the perennial agency problem). We deliberately avoided the tried and tested strategy of scalping clients from our previous employers, so we were starting completely from scratch. As it turned out, a handful of past clients got in touch when they found out we’d made the jump as they felt the relationship was more with us as individuals and were keen to continue the partnership, which was very flattering and really helped us find our feet. 


Image credit: CliQQ Studios

We didn’t struggle too much when it came to building a team as we had a black book of exceptional talent to call upon, but as first-time business owners, learning all the things you need to know (or at least, have a vague understanding of), like financials and tax planning, business development, managing a sales pipeline, and a host of other things you wouldn’t necessarily consider, was a steep learning curve. Fortunately, there’s lots of help out there and people who can advise and support you, so you don’t need to do it all yourself!

Which was the first huge success that you can remember?

Simply landing our first client was huge to be honest. Up until that point, we’d talked a lot about what we were hoping to achieve and what we wanted Cheddar to look like (all the vision and values stuff basically), but it wasn’t until the phone rang and we had a paying client ready to sign up that it all became real. That gave us the confidence that our pitch had at least resonated with one person, and where there was one, there’d be others willing to take a punt on us. We’ve since worked with scores of clients, from micro-startups to international organisations, and had our work recognised by various awarding bodies (including multiple ‘Features’ on Creativepool and being shortlisted for ‘Best Agency to Work For’ and ‘Best Web Project’ in this year’s Creativepool Annual), but the validation of landing our first gig and feeling like we were onto something with our slightly zany brand story was our first big success.

What’s the biggest opportunity for you and your company in the next year?

It’s really hard to say with everything that’s going on in the world right now. Our big hope is to be able to travel and give Cheddar more of an international outlook. We’re knowledge workers and only need a reliable internet connection and a smartphone to be able to work from anywhere. We already have clients in North America, Italy and South Africa and would love to broaden those horizons further still. Cassie is from South Africa and Africa is very much open for business, so we’d like to explore a second base of operations there as soon as we’re able. We’re firm believers that travel and experiencing different cultures is one of, if not the best source of inspiration, especially when it comes to creative endeavours, so we definitely see travel (and global domination!) as our biggest opportunity in 2021.


Image credit: CliQQ Studios

Can you explain your team’s creative process?

We don’t really have a standard process as such as each project, whether it’s web design, brand identity, print, marketing strategy or video production, will have slightly different requirements. Some agencies see clients as the enemy that they have to try to get work past; we see them as our best collaborator, so we’re always keen to get them as involved in our process as they’re willing and able to be.

We tend to start with a discovery phase where we’ll ask ourselves, “what excites us about this product or service and what do we need to know (and do) to ensure we pass that excitement on to the user/customer?” It’s a fairly front-loaded process on paper but we usually find the extra time and effort we spend gleaning insights at the outset is paid back ten-fold when we actually start designing and building. 

We’re sometimes faced with a client who feels a discovery phase is a luxury they can do without, but when we explain why it’s important and show them the outcomes we’ve achieved through the principles of design thinking, they’re usually converted. And if they’re not, we’re happy to walk away as we know it’ll end in disappointment for all concerned. Following the discovery phase, our creative process is very agile, fluid and organic, and really boils down to ABC – Always Be Curious. Everything else is just tools, tactics and techniques. 


Image credit: CliQQ Studios

How does your team remain inspired and motivated?

We have a ‘no arseholes’ policy. There’ll always be something in the brief to inspire and motivate, but if there’s bad chemistry with the client or potential collaborator, motivation will plummet. The trick is to be able to suss this out as early as possible, preferably before you’ve taken the job on. Our onboarding process and prelude to the discovery phase has been designed to identify the traits of arseholiness so we can make a gracious exit before any money has changed hands. And I’m not talking about the avoidance of conflict as that can be constructive and is very much an integral part of the creative process and how we do things. We enjoy being challenged on our thought process almost as much as we enjoy doing the challenging ourselves! No, the arseholes are the ones who seem to be hiring you under sufferance then go out of their way to make life difficult. They’ll never value what you’re bringing to the table so the work you do for them will never be any good. If you detect a whiff of arsehole, give them the bum’s rush. 

We have a 'No arseholes' policy.

With regards to inspiration, we seek it out everywhere. We try (not always successfully) to maintain a good work-life balance and much prefer the great outdoors to being cooped up in an office all day. That’s the big advantage of working for yourself; your time is your own to manage as you see fit. As long as the work’s getting done to the high standard we demand of ourselves, it doesn’t matter if we need to take a morning to get out of the studio and find some inspo. 

How has COVID-19 affected your company?

Without sounding too smug, it hasn’t really. We’ve always worked remotely so we already had a decent set-up for online collaboration and virtual conferencing. Not meeting clients face-to-face was a little strange at first, but again, we’d already embraced the technology required for long-distance collaborations so being forced to work from home was business as usual in many ways. It was tough in the height of the first lockdown as we started to miss the facetime necessary for the more interactive aspects of our creative process. And the bants, of course. We also had a couple of big projects put on-hold and things went very quiet for a few months while everyone adjusted to the new normal and tried to figure out what the hell was going on, but we had enough work to tide us over and the phone hasn’t stopped ringing since July so we really can’t complain. 

We’re a small, agile team with no unnecessary overheads, so we didn’t need to scale down to weather the storm or think about pivoting or any of the other challenges larger businesses have been faced with. We’ve just carried on doing what we do and have been fortunate enough to not feel the pinch.


Image credit: David Chatflied Photography

Which agencies do you gain inspiration from? Do you have any heroes in the industry?

We don’t really look to individuals per se. There’s lots of work out there that we take inspiration from (did someone say, Creativepool Annual?), but we don’t necessarily have industry heroes. Rich fancies himself as Don Draper so he’s always quoting David Ogilvy (and Mad Men) and he’s an NFL fan so he’s an admirer of Bill Walsh’s teachings on leadership. We also like Adam J. Kurtz and how fearless he is when it comes to taking creative risks and just putting something out there that he likes that other people can either enjoy or scroll past, he doesn’t give a shit which. There’s a great philosophy right there for aspiring creatives who might be prone to overthinking and self-criticism.

What is one tip that you would give to other aspiring creatives looking for work?

Be as gritty as hell. Keep on keeping on – the work is out there – you just need to be relentless in your pursuit of it and prove your value. We haven’t experienced a decline in demand for our services (if anything, there’s more demand now than when we were awash with Brexit uncertainty), which suggests design and creativity are being embraced by businesses as potential differentiators. Creatives with commercial savvy will be in hot demand as businesses look to bounce back from the corona crisis so put yourself out there and show people how you can help. It’s Marketing 101 really – identify a need/problem and demonstrate how your product (i.e. you) can solve it.


Image credit: David Chatflied Photography

What’s your one big hope for the future of the industry?

That creativity and the idea economy continues to ride the wave it’s on and doesn’t get relegated as soon as relative normality returns to the business landscape. It feels like design thinking is starting to permeate and gain some ground as a management strategy. The rise of the Chief Creative Officer (CCO) and Chief Design Officer (CDO) suggests ambitious businesses of all shapes and sizes have realised the necessity of leading with design, humanising the brand and crafting authentic experiences that resonate with target audiences if they really want to stand out from their competitors in increasingly noisy marketplaces.

Our hope is the heavy-handed sales tactics associated with lazy marketing, which seems to be dying out at a rate of knots, stays dead and the more design-driven, ethical and socially responsible phoenix that’s rising from the ashes continues to soar. 

Do you have any websites, books or resources that you would recommend?

Where to begin… The usually well-stocked studio bookshelf has evolved into a mini library since lockdown began. The musings of the aforementioned David Ogilvy are well worth a read. Sprint (Jake Knapp) and Gamestorming (Gray, Brown & Macanufo) are particular faves of ours (the latter is the perfect toolkit if you’re looking to introduce play into your creative process). The prolific Seth Godin usually has some interesting things to say, Malcolm Gladwell’s The Tipping Point and Blink are fascinating, as is Harari’s Sapiens (which always pops up on recommended reading lists for creatives), Creativity, Inc. (about Pixar’s creative process) is great, and there’s lots of good stuff in The Science of Storytelling (Will Storr), Good Strategy, Bad Strategy (Richard Rumelt), Change by Design (Tim Brown), The Consulting Bible (Alan Weiss), The Lean Startup (Eric Ries), In Search of Excellence (Tom Peters & Robert H. Waterman) and anything by Peter Drucker. 

Website-wise, we love Creativepool (obvs), the InVision blog – Inside Design – is always worth a visit, Muzli is great for design inspiration, as is Behance, and Instagram of course. We’re also getting into TikTok (yes, we’re late to the party we know) so keep an eye out for our video debut soon!

We do love a podcast but haven’t found one yet on design and creativity that we’ve stuck with. They’re either too technical and inaccessible or tend to get a bit repetitive and boring. Maybe creativity is too subjective to make for engaging and enlightening discussions? Hopefully, we’ll get some good recommendations in the comments.

Header image: David Chatflied Photography


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