Hi-flier’s brand journey — from bland to evocative

Angelique Little
Hi-flier
Published in
10 min readMar 12, 2020

Everyone knows brands are important, though perhaps not everyone agrees on whether brands are created or built. Maybe it’s both. The reality is, all brands have to start somewhere but does a name, logo, and feeling really matter? For a startup, they can make all the difference in the world!

A good brand can help people understand what you’re offering, remember your new product, and envision your success as a company.

A couple of years ago, I started as a brand strategy advisor with Bipronum—a startup with a revolutionary way to organize people, achieve goals, and move business forward. I’d worked with them to solidify their positioning and messaging, but really wanted to tackle the name and develop a visual brand that was as exciting as the product. It was obvious to most people involved with us that the brand could do much more, but without an agency or a design team, I didn’t dare take on a rebrand myself.

Then, the stars aligned, and my preparation met opportunity, propelling a small but scrappy distributed team to create a name, logo, look and feel that would ignite our team around a fantastic new brand.

This is the story of how we did it.

A brand challenge

Our first name and logo were defined in the very early stages of the product, as they so often are for startups. But people couldn’t consistently pronounce it, it wasn’t very memorable, and it didn’t mean anything.

After creating an innovative and valuable product, the name was starting to work against us.

In the last two years, we’d learned a lot about what makes our product different from the plethora of collaboration tools out there and the value we offer. Now, we needed our brand to reflect this.

Our product resonates best with:

  • Freelancers and independent consultants who drive business — not work — without a fixed team, inside and outside corporations, and across their networks
  • People who want to design their own business interactions, and need to flexibly and continuously meet opportunities as they arise

While we always knew that a new brand would make a difference, we didn’t expect that our customers and partners would respond as quickly and enthusiastically as they have!

The beginning of a journey

We started this rebrand process a full year ago, when I completed our first brand messaging architecture which included a vision statement, a set of brand attributes, and key product features. Everyone agreed that we needed a new brand but without a designer on the team, we could only focus on a name.

Those explorations, around a few of the themes that regularly came up, yielded several names that we liked, but most only reflected one aspect of the product, not the whole experience. Additionally, it was hard to put the name to the test without an accompanying logo, look and feel.

Some of the names we considered:

In late October, Kristy Mapp joined the team. A visual designer with a diverse background as a photographer and interior designer, one of her first tasks was to rebuild our website. As she got to know the product and the brand, she began playing around with ideas for a new look.

One day, Tim Bussiek, the CEO, asked Kristy to create a key visual for a deck he was putting together for the editor of one of the biggest women’s magazine in America. He wanted to convey how the product could empower her mostly female team of creative professionals to drive their success inside and outside their organization. Kristy created this image to represent business people achieving business success together.

Having a designer who could visually brainstorm for us was proving to be incredibly valuable! But this infusion of female energy and ideas into a product that had thus far been concepted and engineered by men, was really the leap forward we needed. Tim and I were so inspired by the image that Kristy made, that the three of us began to dabble with name ideas that expressed the user as a superhero, masterminding their next big moves.

Some names we came up with:

  • Max, Maxwell, Super Max
  • Rocket, Jet Pack, Action Pack, Slipstream
  • Phone Booth, Get Smart
  • The Salon, Great Hall

Ensuring a focused approach

Before I knew it, we were diving into a real rebranding effort. And while I was thrilled that we were finally doing this, I also knew we needed to do it right.

We had two driving forces. 1) Finding the right name and brand and 2) Moving quickly.

We couldn’t afford to spend months and months on this, but we also couldn’t settle for something that didn’t meet our criteria.

Our new brand needed to:

  • Be interesting, different, and memorable
  • Reflect our brand attributes and the diversity of users
  • Resonate with and excite our team, customers and partners

I started by putting a deck together about the product experience and brand attributes, around our company mission:

To empower people to create and repeat business success with others in a visual, achievement-driven environment

From big picture to big idea

Without a creative agency to work on this, Kristy and I presented the deck to the team and asked them to submit images that expressed the feelings of brand attributes for our mood board. Our images ranged from abstract and technical, to organic and personal. I even threw in pictures of friends and family in moments of triumph or celebration.

From there, Kristy created a few color palettes and we chose one that was most familiar and looked most like our exploration thus far.

During a brainstorm session, Kristy came up with the name “Pilot” and it immediately resonated. We loved the idea of men and women charting their course to reach a destination, and taking others along. We loved the aspirational aspect of it and the idea of soaring above everything. Kristy mocked up some logo ideas and I reviewed the name against our brand attributes. It worked!

Why Pilot works:

  • Personal > Your ingenuity put into action
  • Freeing > The sky is wide open, where do you want to go?
  • Easy > Pick a destination and fly on autopilot!
  • Efficient > You’re in control, no training required
  • Rewarding > Flying is still a special experience

We added the color palette and logos to the deck then shared it with the team. They liked it too! But there was a concern that Pilot was too specific, had too many other possible meanings, and wasn’t unique enough.

Though we really liked Pilot, I started thinking about alternates:

  • Skypilot, Aviator, Captain
  • Flier, Aeronaut, Aerialist
  • Eagle, Soaring

Ready for inspiration

Then one day, it came to me: Hi-flier. It was less specific than the other options but more aspiration. I just knew it was the right word for our empowered entrepreneurial professionals.

I looked up the definition of Hi-flier and almost fell off my chair. It was identical to how we had described our users. I made a few tiny tweaks to create our own unique definition.

Hi-flier: A person who puts their ingenuity into action to create business success

I shared it with Tim, and he immediately loved it for being even more about ambition and achievement. We floated it past Kristy and we all decided that we didn’t lose anything by giving up Pilot as all of the rationale worked for Hi-flier as well. But with Hi-flier, we gained the aspirational sense of soaring above it all. Next to it, Pilot felt clunky and grounded.

Getting feedback from friends

Kristy updated the preliminary logos and we were ready for feedback. I finished up the brand deck and we sent it to a group of our trusted friends and partners for their thoughts.

Half of the feedback was just positive — great direction, makes sense, love the work! The other half let us know that we weren’t quite there and needed to refine the concept further. I challenged us to address each of these:

  • Mood board lacks cohesiveness. A few people wondered which brand attributes we thought each image represented and challenged us to cull them down to ones we really feel convey the brand. Could we choose just a handful of images that we agree convey the brand values?
  • Colors don’t represent the brand values. A designer suggested that in looking at this for freedom, flexibility, and skies the limit, the dark blue, orange and gold didn’t seem to convey those qualities. Could we revisit the palette for lighter, brighter, colors?
  • Name and visuals look retro. One person said it reminded them of the movie Catch Me If You Can. Another said Hi-flier reminded them of the 1950’s Radio Flyer wagon. The militaristic aspects didn’t resonate. Could we dial back the airline look and make it feel more modern?
  • Balance between individuals and teams. Two people thought that Hi-flier put a lot of emphasis on the individual and didn’t indicate a partnering product. Could we convey the collaboration aspect with the messaging?
  • Messaging sounds ambitious. There was another comment that Hi-flier might be ambitious and not in line with how people think about business. Her concern was that people want their work to be more relaxing. Could we create a sense of rising above it all that feels effortless?

Outside-in gave us the perspective we needed

In a one-hour sync session, Tim, Kristy, and I made some quick decisions based on the feedback to whittle down the images on the mood board, spend more time talking about why the images supported the brand attributes, and redo the colors.

We selected 10 images that represented the ambition, optimism, and ingenuity of our audience. From there, Kristy created a new color palette. We reviewed the colors and discussed the attributes of each until we had ones that best expressed the brand.

How the colors express the brand:

  • CALI BLUE — The color of opportunity
  • CHARCOAL — The color of confidence
  • CADET & POWDER BLUE — The colors of freedom and self-expression
  • CLOUD — The color of possibility
  • GOLD — The color of success
  • CORAL — The color of excitement

Now that we had forward motion, Kristy could finalize the logo using the new colors and a font that felt more in line with our concept. During this final round of design, we found ourselves learning even more about our product and our brand.

With Hi-flier, we went all in on the idea of achievement, the entrepreneurial spirit, and rising above it all. This is an app for people who are motivated to optimize their efforts and achieve more.

The logo has wings and leans forward to express the idea that people who use Hi-flier will fly, with a perpetual forward motion. The use of the dot in the center, instead of the dash, correlates to our shortened brand mark and represents a point on a journey. Our confidence color used in the name sets the tone for achievement while the gold in the dot and wings, represents the individual success of each user.

Though our focus is still on ‘everyday business success,’ the action is now ‘fly.’

Our new tagline is: Make your everyday business fly!

I added a few slides exploring terms we could use in the product to enhance the feeling of being a hi-flier:

Audience testing

Then, we updated the deck and ran it by current users for their reactions. Here are a few.

An independent consultant, formerly with McKinsey, who runs a business as an efficiency expert said:

I like the idea of seeing it from a higher level, I want to see over everything

I don’t care about all the details, I just want to know where things are

I’m okay with the idea of boasting, I want to be a Hi-flier!

A group of college students in Michigan, who are using Hi-flier to collaborate on projects, gave this feedback:

It’s good to sound ambitious

The brand and terminology bring the app to life, and lets me know what to expect

‘Mission Control’ instead of ‘Notifications’? Cool!

A product manager who develops online services such as eBay, said:

I like the aspirational feel of being able to achieve anything

Work should be easy, and this looks breezy and flexible

There’s something so cheerful about the “Hi” in a bubble, it’s optimistic

We were elated to hear confirmation of what we had set out to achieve!

The name and brand communicate our offering of an app that supports people’s ambition and organizational talent for business success.

As expected, the brand also gave us a unified direction for messaging using hi-flying as a simple and effective guiding idea.

Time to celebrate

We hit it! With a combination of preparedness, inspiration, and skill, we finalized the brand and showed it to the team. From there, we moved very quickly. I created a timeline for how to roll it out, Tim researched and secured a URL, and Kristy put together ideas for how it would look on our website, in email, and in the product.

Our new website is up, with our new look and feel, at www.hi-flier.com but ideas of what we can do with this brand just keep coming. Stay tuned to see where this small but scrappy distributed team will go using Hi-flier!

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Angelique Little
Hi-flier

User experience expert and filmmaker. Currently a Content Designer at Dropbox. Formerly at Chegg, Facebook, and eBay. Words matter.