Since its launch more than a decade ago, FreshBooks has achieved an unlikely end-goal: making DIY accounting feel painless, quick and even fun. Going cross-eyed over spreadsheets isn’t usually part of the self-employed dream — but it can easily become part of the reality.

Jeremy Bailey, FreshBooks’ Creative Director for Product, played an instrumental role in establishing FreshBooks as the go-to cloud accounting software for small-business owners. Initially hired as a freelance art director, he joined the team full-time in 2010, delving deeply into users’ problems to connect a relatable marketing experience to a product that genuinely helps its customers. Marketing and product can often seem like their own realms, but Bailey has a foot firmly planted in both worlds. (He also works as a visual artist under his tongue-in-cheek alter-ego, Jeremy Bailey: Famous New Media Artist.)

As part of our ongoing interview series with awesome product people, we chatted with Bailey about stripping brands back to their studs, ditching your biases, and the Wild West. Like, the literal Wild West.

Your title is pretty unusual. How did you come to be Creative Director for Product?

I was freelancing and FreshBooks was a client that came to me with a problem. I think a lot of startups probably have this problem: different people have come and gone really rapidly over the first few years. And different people have put their flag in the ground. So there were a lot of arbitrary and sometimes well-guided decisions, but altogether they don’t add up to a cohesive whole. That was definitely true for FreshBooks, not for any mal-intent, but just for the sheer speed at which they were operating.

They hired me to help bring that all together. And the first thing I did was wrong, too. I proposed a sweeping new look. And the humbling lesson that I learned is to figure out what their customer needs. So that became my job. And what I discovered by talking to the customers and spending time with the staff was that what they already had was wonderful. People already loved what they were doing. There were certain aspects of their brand, not visual, that people were over the moon for. Like their support, or the little things their product did to make them laugh. And the things the customers really loved could be applied more broadly across the whole product and platform. The whole image of the company.

How did you calibrate design changes that went “too far” vs. changes that would have value?

It was a very simple strategy that’s the same strategy every home renovator uses on a home decorating show. Which is to strip it all the way back down to the studs. And say, “What is the least we can have and still evoke these emotions?” So visually it would be removing all the drop shadows, the gradients, the additional flourishes, and saying, “Hey, we’re going to stick to a really simple color palette, and exercising some restraint will help us find out what’s essential. And when we hit a roadblock, we’ll add to that palette. And by pulling all the way back and then adding, we’ll understand how each decision was made.”

I was able to help arbitrary decision-making become more structured decision-making.

How far back did you strip it, exactly?

We went back to blue and white and black. Which were the colors of the logo. And green for calls to action. And I got rid of all the non-heritage, non-long-lasting typefaces, because I knew they’d have to be replaced. And we just stuck with that.

“You don’t invent the brand. The customer invents it and then you just reflect it back to them.”

We were using stock photos for our illustration, and I knew that wasn’t going to help us stand out. This was Web 2.0 era, and there were probably 30 competitors doing the exact same thing at the exact same point in their progress in the market. So there were 30 other brands people loved. My experience told me that if you want to stand out, you need to do something other people can’t do. And you don’t copy what others are doing. So constrain our palette, and then start to do things that others couldn’t copy.

It’s really basic. I kind of feel that anyone could apply that tomorrow and improve their brand. But then the more difficult thing in the longer term is: “How do we translate that same approach to the product?” At first we just did a visual scrub of the product, but for the last three years I’ve been really focused on bringing that same decision-making, consistency and restraint to the product.

Do you have some advice around how to exercise effective constraint?

One thing we did at FreshBooks was make it really hard for a single individual to make an arbitrary decision. As an example, we formed a little council that supervises every visual decision. We call it “art director’s circle.” When you want to change an element that’s core and that impacts different aspects of the brand, you come to that council and you make a case for it. It’s not like a tribunal in a negative way, but there’s a structure to the argument. And every time we’ve thought, “This is going to be an easy decision,” it ends up being a really hard decision. And I’m glad we make those decisions early on, and not after it’s out in the wild — when we’re like “oh shit.”

What kinds of considerations go into that decision-making process?

There are different vectors. There’s some standard stuff. Is it accessible? Is it on-brand in terms of just the pure guidelines that we have?

“I don’t think any customer wakes up wishing for their company to rebrand.”

The conversation goes something like, “Here’s the problem.” We show the problem, then we ask, “How are others solving this problem today?” So we might look at how other brands are solving that problem. Then we’ll stress test the solution. When you’re building those guidelines, you’re trying them out, not just on your marketing, but you’re also trying them out on the product. You’re also trying them out on your advertising or your corporate communication.

This whole exercise doesn’t take more than a week, but we do that for each major decision.

It can be hard to correlate design changes directly to, say, a boost in conversions or revenue. How do you make a case that design changes add value?

All these things add up to emotion, and if you feel like you’re coming out with a message and you’re not reinforcing that message, then of course you want to align them with that, because that’s going to help people understand with greater impact. You only have a few seconds of a person’s time when they first meet you, and if they’re wearing bedroom slippers outdoors in the snow, you’re going to be like, “What’s going on here?”

I think it’s best to think about brands as people. And I always think of them as a reflection of the people we serve. Basically you’re trying to reflect back to that person, “Hey, I’m for you.” Not only am I for you — I look like you, I sound like you. It’s a trust thing. You don’t invent the brand, the customer invents it and then you just reflect it back to them.

Why do you think it’s often a challenge to create consistency between product and brand?

Most companies are organized in silos for product and marketing. And they do their thing. And in fact, they often become enemies. I don’t think that that’s always the intent. But, “Oh marketing did this” is a common refrain I’ve heard in my career. There’s exclusive language to both disciplines, and they’re sometimes in opposition.

What mechanisms have you tried to break down silos?

I’ll be very honest, I’ll say that’s my biggest challenge. But in the past, where I’ve seen the most success is when you have everyone on the same team.

So no more, there’s a marketing team or a product team. You have a team that delivers an experience. And a marketer is a part of that team. And a marketing designer is part of that team. And a product designer is part of that team. And everyone understands the goal, and they’re all pushing forward together toward that goal. I’ve never seen a team work better together and produce higher-quality work at as great a capacity without any friction or tension.

The problem is when you create two different goals that aren’t aligned. On two different teams in two different sides of the building. Geography actually matters. Just like talking to a customer, the same thing is true internally. Sitting next to the person that you’re going to work with creates at least some sort of empathy for the other person’s predicament.

How does it benefit a company to have more consistency between the branding and the product?

When you have consistency you can put arguments to rest over taste. I don’t care that your husband or boyfriend or girlfriend or wife has an opinion on the color we should use. Let’s just establish this is what we’re going to do, this is performing well, and move forward because there are so many other challenges that are as important or more important. I don’t think any customer wakes up wishing for their company to rebrand. They’re more likely to switch brands, frankly, if you do that. One of the decisions I had to make was not to update our logo seven or eight years ago. Because that was the thing people recognized and loved and they weren’t complaining about it.

“The gut instinct you have in your corporate office is 9 times out of 10 absolutely not correct.”

I always explain this cocktail party analogy. A logo is a lot like someone’s face. And if you meet someone and they’ve changed a little bit over time, you’re usually like, “Wow, it’s been so long, I haven’t seen you, you’ve changed so much.” But if you come back two weeks later and they’ve changed their face again, you’re like, “Something’s wrong.”

With consistency, you’re taking that objection off the table. This is a trustworthy company. That’s why brands existed in the first place, was to establish trust. Because there was a Wild West out there, literally, where companies were making all kinds of elixirs and stuff like that.

How can product managers support design in creating symbiosis between product and brand?

That’s really easy. For us, anyway, we always thought of the product manager as a designer. Or working alongside the designer as a perfect couple. If they’re working well, those two people are essentially two halves of a whole solution for building product. So the designer leans towards design, and the manager leans toward the practicality of development. But together they form a whole unit that can deliver outstanding results.

At FreshBooks the research used to be entirely done by product managers. But now they share it evenly. Design decisions used to be entirely by the designer, but we have several meetings where we do critique, and the product managers and designers critique together. They also ideate together. So at all the key junctures, they’re considered the same person. They’re reporting together, they’re demoing together, they’re like a little pair.

Can you tell us about your research process at FreshBooks?

We’re either talking on the phone or inviting people in to look at products, or going to their offices to learn about the problems they have. So every designer talks to four people a week. That kind of customer intimacy is irreplaceable and it creates an intuition for what the right thing is, instead of going on your gut. The gut instinct you have in your corporate office is 9 times out of 10 absolutely not correct. It’s informed by privilege. And those privileged decisions are informed by an unintentional bias that unfortunately makes us make wrong decisions on behalf of our customers.

“The worst thing you can do is look at your competitor and copy that.”

Last year we spoke to over 1000 people, this year we’ll probably speak to twice that many. When you do it on a regular basis it becomes natural. Our natural instinct is to defend our position because we don’t want to admit we’re wrong. And we find data to back up our biases, and confirm our biases. And so I think it’s really important to get out and talk to the real people.

What’s the worst mistake a company can do when trying to create consistent design that runs through product and marketing?

I think the worst thing you can do is look at your competitor and copy that. It’s worth emphasizing, because it’s a natural instinct when you’re small to look at what the big guys are doing. But I can’t emphasize enough how backward that strategy is. The fact that you’re small is actually your biggest advantage.

A great company that came to my attention — probably too late, but who I’m in love with right now — is Everlane. Their concept is radical transparency. And as a very small online retailer, they leverage the fact that they have no brick-and-mortar stores to offer a cheaper price and to be transparent about their markup, and to show you their factory. So all the things the big guys couldn’t do, they’re like, “This is our brand.”

How have you leveraged this idea at FreshBooks?

With accounting software, they’d say it should look like business software. “This is too playful.” Right? But that’s precisely how we distinguish ourselves versus the most corporate giants in the world. If we went out and did exactly what Intuit or Quickbooks did, we’d look like a lesser version of them.

“For me, it’s the humility to understand that big problems require teams to solve.”

But we come out and we do what they can’t do. They can’t use a playful tone, they can’t be transparent, they can’t pick up the phone. You can’t talk to the CEO. You have to play to your weaknesses as your strengths.

Looking back at when you started at FreshBooks to now, what’s the most significant way you evolved as a designer?

For me, it’s the humility to understand that big problems require teams to solve. You need to push down your problems to the team and collectively solve them, because ultimately they need to be implemented collectively.

That’s something I still work on today: how do we create organizations that emerge from the bottom? That aren’t driven from the top. Organizations where every day you come into work, and when there’s a problem you don’t just say, “Ugh, well I guess we have to deal with it because it’s the corporate way.” But where you’re like, “This problem could be solved if we work together.”