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By Dick Maggiore and Mark Vandegrift

Brand Distinction Pirate Ship

Yo Ho! Pirate Ship weighs anchor with brand distinction in a sea of sameness

Not long ago, I got an email from LinkedIn with a digest of “Top job picks for you.” I’ve been at Innis Maggiore for over two decades and am not in the market to change that, but the first listing caught my eye. It said I was a high skills match for the job of Vice President of People at a company called Pirate Ship®. When I saw a logo that was a simplified icon of a Jolly Roger, I felt the call of the high seas and clicked through to explore. Little did I know I was embarking on a whole brand distinction adventure.

Any buccaneer with an eye patch could clearly see that I was absolutely not a match for this job because it was in human resources. However, as soon as I saw that the position was internally called Vice Pirate of People, I was compelled to read on. (It should be noted that all of their job postings have swashbuckling swaps, such as Senior Dubloon Defender for Senior Fraud Analyst.)

The responsibilities were detailed under headers such as Sail the Seven Seas, Tend to the rigging, and Splice the mainbrace. The listing declared their three pirate codes and the values that reflect “Who We ARRrrr.” Under “Bonus points for/Preferred Qualifications,” the very specific skill of “YARRrrr! The ability to speak like a pirate!” was noted.

Just like J.M. Barrie’s classic captain, I was HOOKED.

As someone who lives and dies by a theme (I mean, I’m listening to pirate music as I write this), I couldn’t believe that a shipping company could be so ... FUN. But the next click on my metaphorical treasure map took me to, and my creative heart skipped a beat. I felt like I had found a glittering trove of doubloons in the sand of the internet.

Ahoy, mateys!

Bjorn Borstelmann founded Pirate Ship with Jameson Morris after pioneering the subscription boxes of the 2010s. Having experienced the logistical frustration of generating shipping labels for thousands of packages each month, the two set a course to develop new software to make the process easy.

Over the horizon in 2014 sails Pirate Ship — making shipping packages fun and cheap for small businesses. They partner with other big-name shippers to offer deep discounts with free site registration and no additional costs.

So, why pirates? In this 2019 article about Pirate Ship’s unique approach, CEO Borstelmann said “Who better than pirates to help you save your booty and have a fun time doing so, as well?”

“Everything was so boring – all cookie cutter – there was no pleasure in shipping at all. From a designer’s point of view, if you can make something enjoyable, you’ve got a better business.” Well, blow me down! I couldn’t agree more!

Dead men tell no tales.

As I dug into Pirate Ship’s website, the attention to detail sent me to Davy Jones’ Locker. I was figuratively deceased at the level of commitment to the theme.

First, we should talk about the name. Choosing a name is a highly challenging first step in creating a brand because you’re trying to convey the core of who you are in just a few words. Pirate Ship is one of the most brilliant executions of “say what you do” with a creative twist that I’ve ever seen. We’re pirates ... who ship things. Brand distinction right off the batten. Blimey!

The thematic copywriting is top notch. Pirate puns are intricately woven into the fabric of how the software works, making a rather boring subject amusing and engaging. Their demo videos feature so many blink-and-you’ll-miss-it Easter eggs that I found myself watching multiple times so I could enjoy them all. Names like Anne Bonny, Long John Silver, and Cap’n Crunch. Sample products like the Eyepatch o’ the Month Club being shipped from One-Eyed Pete’s Eye Patch Warehouse. Destinations like Emerald Isle, Bahama Bay, and Shoreham-by-the-Sea.

The graphics on the clean and breezy site mix a tropical, seafaring motif with common shipping items, boxes, and labels — one page even showing bone-shaped packing peanuts strewn about. The testimonials depict happy pirates proclaiming the joys of using the software. They also include photos of their shipwreck-themed headquarters in Jackson Hole, Wyoming.

These savvy shippers could bellow a rousing sea shanty about how much they love Pirate Ship. Source:

The theme extends all the way through customer service, where their crew is trained in pirate speak and highly encouraged to use funny gifs in their chats with customers. Pirate Ship’s site has a bounty of glowing reviews, of course, so I made haste to reddit for the real tea. Users were overwhelmingly positive about the company’s low cost, ease of use, and excellent support. One redditor said they use the service “because when they email me, it starts with “Ahoy!”

And don’t even get me started on Pirate Ship’s brand guide, The Pirate Code (download it here). I’ve seen many a brand book in my years as a designer. Some prattle on with pretentious explanations and diagrams that nobody ever asked for (or will ever need). Others burst with a million ridiculous ways not to skew the logo.

But the Pirate Code is a mermaid’s kiss. Cap’n Bjorn wants his crew of sea dogs to have a blast with the brand. And it shows.

Taking a quick peek inside their Brand ARRrrrsenal, you’ll see what I mean.

  • a custom font called ARRrrrial
  • a set of piratey ARRrrrmojis
  • color themes of lightmode (canvas white), darkmode (flag black), and drunkmode (Tipsy Bay)

Aye, these scallywags just get it.

Everyone at Pirate Ship is in on the bit, and having fun is serious business. How many CEOs do you know with enough moxie to use an image like this as a corporate headshot? Source: The Pirate Code.

Not all treasure is silver and gold, mate.

Positioning tells us to find and focus on an idea that differentiates the brand from the competition in the mind of the customer. I’d say Pirate Ship has cracked it. They live and breathe their brand and ARRrrr not afraid to shout if from the crow’s nest. “Make shipping fun,” they said. And they did.

“Some of the best brands in the world go as integrated as possible,” says Borstelmann. “Disney doesn’t slap a logo on something and call it done; they build an experience.” As a proud Disney adult who subscribes to that philosophy, I can confirm that this brand was a high-seas adventure for this humble landlubber. You might even say it shivered my timbers.

Crafting an immersive brand experience is one thing. But backing it up with a great product that creates happy customers who are all-in on the schtick? Pirate Ship’s competitors may have to walk the plank.

Solve a pain point – check. Make a dry subject entertaining – check. Take a sharp left turn from any other shipping company in the industry – check. There’s no doubt what this company stands for.

So what can we learn from this jolly band of pirates? Borrowing from their own words, “Be true to who you ARR.” And never apologize for it. The bigger your brand distinction, the higher your value. I would give an arm and a peg leg for more brands to be so dedicated to steering away from the norm.

In a world where so many stugy corporations sail the sea of sameness and are afraid to have fun, I want to be a pirate.

Avast ye!

Don’t get hornswaggled into thinking your brand needs to be boring. We can help you chart a course to plunder the hidden treasure you’ve been seeking. Hoist the mizzen, and let’s head out on a brand adventure together.