From product designer to agency director

In late 2017, I quit full-time work to freelance. The plan was to spend a couple of months designing products in industries I didn’t know, figure out what I actually cared about, then decide where to work next. Freelancing would keep me afloat in the meantime.

Instead, I ran an agency for four years.

Hayden and friends

I was lucky with clients early on. Within the first few months, people were asking for complete rebrands and product redesigns, work that needed a small team of designers and developers rather than one product designer. I’ve always found it hard to say no to a client, mostly because I like seeing how much I can help and how far the relationship can go.

So I subcontracted the extra work to people I’d worked with before, at past jobs or just friends. That worked well until demand kept rising and I noticed that pitching “Hayden and friends” wasn’t particularly clean. About three months in, I incorporated Jellypepper and moved into creative direction and operations.

Because everyone on the team had come from startups, we ended up filling a gap in the market: an end-to-end agency for startups that didn’t feel like working with an agency. Over four years we worked with startups in self-driving car tech, AI, biotech, crypto, drone delivery, cybersecurity and even orbital logistics.

Growing too fast

Going from product designer to agency director meant learning a different job, mostly by making mistakes.

At first we took on any creative work a client needed, because it meant we could give them more. It took nine months and a few project mishaps to learn that taking on every problem at once isn’t a sustainable way to solve any of them. So we cut back to what we were exceptionally good at, wrote playbooks for our product design process and partnered with freelancers for things like video and photography.

Jellypepper also grew from a small studio to a medium one much faster than it should have. I was getting 60 new emails a day and only had 30 minutes a day to answer them, so clients and leads sometimes waited up to three weeks for a reply. They were patient, but it wasn’t sustainable. I’d wake up every morning to a slew of Slack messages about overdue tasks and people who needed things, and that was before accounting, BAS, payroll and superannuation.

For a while my workspace was my bed, away from any decent light. Combined with 16-hour days, that led to a solid vitamin D deficiency. I eventually bought two desks and put them next to a big window. You won’t get very many sales if you’re sick or dead.

Early on, I came close to throwing in the towel. What helped most was Run Studio Run by Eli Altman, a short book about running a small creative studio.

Getting on top of it

Agencies grow, but they don’t scale the way products do. Every new client means more people to do the work, so the only way to keep up was to stop doing the same things by hand. We made templates for questionnaires, briefs and moodboards, wrote a standard pitch and automated our proposals and agreements. Every lead went into a CRM, from their first visit to the follow-up after a project.

It took months, and it was just in time. Another week of typing up proposals for leads that went nowhere would have sent me over the edge. Once it was all in place, things went quiet. It took me a while to realize that’s what being on top of everything feels like.

I also got stricter with my time. I had 10 to 15 client meetings a week, so I put them back to back on a couple of days and kept the other three for deep work. Internally, we barely had meetings at all.

Sales got easier too. We published our values on our website, which meant fewer leads, but the ones we got were people we already wanted to work with. From there, the approach that worked for me was just being upfront about what we did and how we did it.

Stepping away

There was one thing I never got used to. An agency only ever has a second-degree relationship with a client’s product. I like being invested in what I work on, literally and emotionally, and you can’t really do that from an agency. Even when you love a product, your involvement has a hard start and end, and the budget sets the limit.

Before Jellypepper, I’d worked directly on products, helping come up with them, build them, launch them and grow them. After four years of watching great products come and go, I realized I’d rather work on one product and make it the best in its market. I figured if I didn’t step away then, I never would. There’s no perfect time to change tack.

So in late 2021, I joined Corellium as Chief Design Officer, and I’m now its Chief Product Officer.

And as of today, Jellypepper has been acquired by Raw Studio.