Designing Willa — Part 1, Discovery

Learn about how we came up with Willa, a new fin-tech app for creative freelancers

I am Head of Design at Willa, a fin-tech startup co-headquartered in LA and Stockholm. My background is 20+ years of storytelling, visual design and product design. I was early at King, Spotify and iZettle (now part of PayPal) as well as co-founder of a few businesses over the years.

In a series of posts, I’ll describe how we envisioned and designed the first version of Willa. A service for freelancers (and their clients). My perspective is one of product- and visual design.

Back in March 2020 when I started working at Willa full time, everything was still a myriad of unknowns and uncertainties. We did see that freelancing was big and growing. In the US, hitting $1.3 trillion GDP contribution from 57 million freelancers in 2020 alone. Not only that, virtually all systems (financial, regulatory and technical) had been made for the old model of company<>employee or B2B. Now that did smell like an opportunity.

The problem

As a product designer, having a clear and defined problem is a luxury. If you solve it, you know you are creating value. And it offers invaluable focus.

At Willa we decided early on to focus on the two biggest pain points for freelancers we could find; their hate for admin, and their cash flow problems. Freelancers spend on average about one day on admin and one day on sales every week, leaving just 3 days for doing their “actual” work. Having worked with 10k+ creative freelancers in our other business Relatable, we knew about this first hand. We also conducted extensive market research on the topic, which provided internal guidance, and some very convincing data for our pitch deck.

How freelancers spend their time, and a summary of what we wanted to achieve

One key insight in this space is the tension between how companies want to pay, and how freelancers want to get paid. Since freelancers are incentivised (they want to get paid after all) they try to accomodate the client as best they can, getting the short end of the stick. But not without creating lots of problems for both parties. One early idea was to make the freelancer<>client relationship assymetrical. What if both the freelancers AND the clients could have it their way?

A note on data driven design
Data driven (or data informed) design is great. Make the thing that gives you the best result. Easy, right?. But this approach is not for taking the big leaps, it is for optimising. Great for A / B testing a landing page, not so much for innovation. It is for choosing a path, not discovering one. Instead, start with researching the now through surveys and interviews.

Initial product discovery

Product design is a web of business development, exploration in messaging, visual prototyping, user research, development, anthropology and sudden inspiration from unlikely sources. It is all this and more, often in a tangle where one thing pushes the other parts forward sometimes in a way that defies explanation.

Thus I prefer the term product discovery, signaling that it is something you find as you venture out and explore, with as much learning as creating.

With that said, you can do many things to help increase your chances of success on your adventure.

So we knew we wanted to make something for freelancers, that helped them in their business, but felt like a B2C product. And while we wanted to help freelancers, we couldn’t do it at the expense of their clients.

If there is no uncertainty, there is no room for creativity.

I love phases of exploration and uncertainty. You cannot move straight from one order to a new order. For innovation to happen, you need to make a pit-stop at messy. While exciting, this phase is also full of frustration and angst. Make sure you have some method to the madness. It will award you with a structure, but also a sense of momentum and avoid skipping important questions that need to be answered.

Our process for product discovery has looked roughly like this

1. Problem (what are we trying to solve)
2. Understanding (what is really going on)
3. Exploration (how could it be radically different)
4. Direction (a vision)
5. Testing (ensuring we are on the right track with a scrappy alpha)
6. Looking the part (with a visual design)
7. Launching our MVP

Let’s dig a little deeper.

Broad exploration

Willa is backed by some really great investors, and at the time, we had a pitch and a very rough prototype of… something. But as all such things are, even though the problem was well defined, our solution was a shot in the dark and we had really no idea if it was anywhere near what we wanted to do. So the first thing we did when we started working after our seed funding, was to start over from scratch.

Early UX drafts from our first pitch deck

After wiping the board clean (but not forgetting anything we’d learned) we went ahead with creating very rough paper prototypes of potential product solutions in a collaborative format (using the Google design sprint methodology https://www.gv.com/sprint/). We relentlessly challenged everything that seemed broken or complicated for freelancers as they are trying to get paid.

Early ideas explored concepts around smarter ways to invoice, budgeting, the value of not caring, CRM functionality, project management, setting goals and much more.

This was a great start, tons of ideas and potential solutions. And as things go, there are always many solutions to a problem. So which one was right for us?

So why not define the direction first? The order is less important than the contrast. Product discovery is a pendulum of opening up and finding focus. A pendulum process is great for creativity which works best when applied in conflict.

• A solution space framed our problem (focus).
• Exploring solutions (opening up).
• Vision and direction (focus).

Next step was finding our vision and a clarifying our direction to help us pick the best ideas for us. Read about it in Designing Willa — Part 2