How I Did It: Rebranding 2 Companies and Staying Sane

Brian Sierakowski
ART + marketing
Published in
8 min readAug 9, 2016

In every aspect of a company, there will always be lessons to learn. Recently TeamPassword went through a major rebrand, and let me tell you, I learned lessons. In fact, many of the lessons I learned were actually reminders from the last time I was involved in a big rebranding project at OrderUp.

The experience of working through a branding project was the same both times: highs and lows ranging from excitement to despair, questioning on if it’s even possible to get to the right answer, and the insanely gratifying “click” that happens when you find something that works. (Then, sometimes, going back to the drawing board again.)

If you and your company are going through the inevitable growing pains of branding (or rebranding), take a look at the following pieces of advice:

It’s its own project

Every time I’ve been involved with a branding project, the temptation is there to make rebranding a part of something else, like a new marketing site or product launch. I’d avoid changing the brand in the middle of another project for a few reasons:

  1. Rebranding is complicated, and takes real, dedicated focus.
  2. There’s a big aspect of creativity and acceptance, which will mess up your product launch timetable if you don’t build in time for “feeling out the new logo.”
  3. Rebranding is highly prone to reversing direction and repeating steps, if you try to build a new marketing site around a half built brand, there’s a good chance you’re going to throw a lot of your work away (both in design and copywriting.)

A branding project deserves as much time and focus as any other project — perhaps more so as your brand may outlive any revision of the marketing site or product you launch.

Always work with professionals

Every project has seems to start the same way. First, you’re shocked with how expensive the project will be, however, it ends with a deep, existential level of relief that you didn’t try to do this yourself.

We are huge fans of working with the pros. Here’s why:

They’re pros for a reason. These guys and gals know what they are doing and have put the reps in. I’ve done it a handful of times in my career, but this is all they do. They know what works within your company’s industry (because, of course, they’ve done it before). They have all the skillsets needed internally to get the job done, and, they have the toolkit to make sure their team is as effective as possible. That toolkit includes both the actual tools, and the soft skills needed to push and sell you on new, crazy directions.

Speaking of which, the second reason behind using a professional branding agency is that they will look at your brand and your company with an objective eye. Regardless of how hard you’ll try, you’re too ingrained in your own company to see it as an outsider. You live and breathe your company, it’s part of you, trying to do your own rebranding is essentially like performing open heart surgery on yourself.

An agency will come with fresh ideas and new ways of looking at what you already have and where you want to go. This doesn’t mean that you shouldn’t pipe in your vision or ideas.

You are absolutely the authority on your company.

However, serve as a stakeholder in the process and see what the pros come up with.

And a third reason, as if you need any more convincing, is that you’ll drive yourself less crazy by taking this one thing off your already full plate. Per tip number one, you have other things going on, and having someone focused 100% on getting this project done will be great for your sanity.

Finding the right pro will depend on you, your company, your personality, and how much time and money you have to spend — there’s no one size fits all option. However, I can personally recommend both Nelson Cash and Ocupop as they’ve both done an amazing job for me in the past.

It’s probably, very likely — okay absolutely going to be uncomfortable

Change is hard. You’re changing something that has a lot of your identity baked into it, and it’s difficult when the point of the project is that said identity not being good enough.

Many companies I know put together their first brand over a weekend and don’t get around to revisiting their brand for 3–4 years, by that time, common law branding has set in and you’re married to what you have. It’s going to be uncomfortable straying from what you’ve always known in your brand, but this is the time to push yourself and your company by not being afraid to take a few risks.

It’s going to feel exciting, too. One of our goals in rebranding TeamPassword was that the old brand didn’t match the strength and excitement of the company — we kicked off the project so that the company would look like the kind of company we wanted to work for.

With that said, always pay attention to your gut.

If you’re giving a new direction a fair chance but you’re still not feeling it, don’t be afraid to turn the car around and go another route. I’ll talk about that more next, but, the trick is to push past the initial discomfort of “this is new and different,” to find new and exciting types of discomfort.

It’s probably, very likely — okay absolutely not going to be right the first time

Somewhere in SOMA, an office is filled with young, excited designers. The smell of coffee emanates from french presses distributed every 3 feet, and the background is filled by that one band that every pandora station eventually gets to (Probably the Lumineers or something). There’s a dog in the office, and someone talks about how important the dog is to the company, giving them a job title like “Director of Cuddles.”

Then, without warning, a beam of light strikes down from the heavens onto a Macbook.

Before the kickoff meeting has been scheduled, a brand identity has willed itself into existence, balancing both the playfulness of your company culture but the seriousness of the problem you solve. It pays homage to where your company has been, but sets its sights on the future. It’s distinct and iconic, but works in every application.

A divine brand intervention has occurred...

Yeah, that doesn’t ever happen. The first draft of your branding isn’t going to be exactly what you will want to go with. This stuff takes time, and a part of the process is thinking about the new branding that might apply to your company. You may come back to the first round of work with better eyes after seeing other ideas.

You have to let it flow, and that means accepting that the creative process is, indeed, a process. Take the first prototype, and go from there.

Don’t worry about the brand until you find some product market fit

A great brand serves many audiences, the internal team should look to it for inspiration on what they can achieve and what’s possible. Potential employees should look to it to have an idea of what it’ll be like to join the team. Customers should look to it to determine if you’re legit, and if you’re well suited to solve their problems, both from a feature standpoint and a culture fit standpoint.

The issue is, until you get some traction, you don’t really know who you are, and you might not even know what you’re doing.

Before you hit product market fit, not having an iconic brand isn’t going to slow you down: not having a product that solves a real problem for a real customer will.

When you’re feeling good that you’re solving the right problem for the right people, you can start to dig for signs that it’s time to update the brand. If people aren’t signing up because they feel it’s ‘not for them’ (and you know it is), or they don’t trust the company, or they don’t know what you do, an brand can do a lot of that heavy lifting.

From personal experience, we had to learn if we were selling to security, or productivity, or both, or neither, before establishing a brand made any sense.

Build a brand system

A brand isn’t just a logo or a color palette, a robust brand will have a system built around it. That means having sensible guidelines in place around details of the logo, placement, and messaging.

These guidelines will run across your entire company for the sake of consistency. You don’t want to confuse your customers/clients with opposing sounding messaging or different looking logos. These guidelines should be built purposefully, and every detail should have an explanation. If anyone asks “why is the spacing like that” and you respond “looks cool”, that’s probably a sign you don’t have a robust brand system.

At this point, even the finest details matter.

You have to remember how your logo translates into different sizes, such as avatars for social media and app icons. Even your messaging is at stake. What do you sound like on your website and app description? Is that the tone you want to continue with on social; a platform which will be updated more often?

Some companies publish their brand guidelines for anyone to see. This holds them accountable for consistent messaging, brand representation, and look, and attempts to limit any sloppy usage of their identity.

Talk to your customers

You know how your new brand makes you feel, you know how your agency partner feels about the brand, but it’s critical to understand how your current customers feel, and especially important to understand how potential customers feel.

This doesn’t need to be a super refined process, a little bit of triangulation is better than nothing.

Get a focus group or two together to give you some insight. Or, reach out to a prospect or current customer you have a relationship with.

You don’t want this feedback to be design advice or which colors are going to make sense. You want to know how they react to the brand, and how it makes them feel. You want to know if they get the “why” of your company, and do they understand the “what.” Feedback on the “how” is rarely useful and should be avoided.

Always summarize this feedback, and bring it up like: “3 out of 4 people I showed this to felt like it was off balance, like we were going to roll down a hill and crash. Does anyone else see that? Should we think about addressing that issue?” If anyone says: “I showed it to my Dad and he said green would be nice” they should be immediately and unceremoniously be ejected from the feedback session.

If you’ve gotten this far and are looking for a reason to ignore all of that advice, here’s a final, overriding recommendation:

Keep going until you have something you’re proud of.

Not something you like the concept of, or that you think tells a nice story, something that you’re personally proud of that represents your company and what you want it to be. If you’re investing in a new brand it should be something that you’re thrilled to put on your back (literally) and carry for the next 3–5 years.

If you’re proud and excited, that will come through to everyone experiencing the company.

*Disclaimer time: I left OrderUp 3 years ago. Since then, they have gone through many wonderful evolutions (like getting acquired by Groupon!) so naturally their branding has changed yet again. The logo added to this post is the one that came from the rebranding that I was a part of. To see their brand new look, check them out here!

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Brian Sierakowski
ART + marketing

Brian Sierakowski is the CEO and lead password-spreadsheet-killer at @teampassword