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Ahoy, personality! What CPAs can learn from a pirate-themed shipping company

July 24, 2025
in Accounting
Reading Time: 3 mins read
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Ahoy, personality! What CPAs can learn from a pirate-themed shipping company
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Enjoy complimentary access to top ideas and insights — selected by our editors.

I recently had to send out a bulk mailing to clients and ended up using PirateShip.com to help. Pirate Ship is a discount online shipping site that somehow manages to make the mundane experience of buying postage and shipping packages genuinely fun. The company’s entire brand is built around—you guessed it—pirates. Emails start with “Ahoy!” Support team responses are filled with nautical puns, and the help desk signs off with phrases like “ARRRgards” and “We’ll be floating around if you need us.” It was a quirky, unexpected, and incredibly refreshing experience. (Disclaimer: The author receives no compensation or promotional consideration from the products and services mentioned in this article.)

It got me thinking. If an online shipping company can inject that much personality into something as mundane as postage, what’s stopping CPA firms from doing the same? Too often, accounting firms hide behind a veil of professionalism that borders on sterile. And while credibility and accuracy are obviously non-negotiable, a little personality can go a long way toward separating yourself from the pack and creating memorable experiences for clients.

Personality is a differentiator, not a liability

Clients don’t just hire CPA firms for tax prep or financial statements. They hire professionals they can trust with their confidential financial information—people they enjoy working with. In a market where so many firms offer similar services, it’s the experience you provide to clients that can set you apart. Adding personality isn’t about being silly or gimmicky; it’s about showing clients that there are real humans behind the numbers.

Here are five ways CPA firms can embrace that idea:

1. Build a “character” brand identity

Craft a firm personality around a theme or metaphor that reflects your mission. Maybe you’re the “Financial Sherpas” who help clients scale their financial mountains. Or you’re the “Money Mechanics” who fine-tune complex financial engines. Once you’ve decided on your unique firm identity, make sure you carry it across your client communications, your website, your social media and even your internal culture.

2. Onboard clients with flair

The onboarding process is often dry and paperwork intensive. Why not surprise new clients with a welcome box? Include a branded mug, a “Tax Survival Kit” or a passport-style booklet explaining your process. These kinds of small, thoughtful touches set the tone for a long-term relationship.

3. Give your communication some character

Instead of signing off emails with “Sincerely,” try something more memorable and brand-aligned such as “Balancing books & peace of mind,” or even something client-specific and fun. Use casual headers in newsletters, incorporate tasteful humor, or send out short, punchy video check-ins that let your firm’s personality shine through.

4. Turn tax season into a positive experience

Let’s be honest—tax season is stressful for everyone. But it can also be a shared journey. Maybe you can create a “Tax Season Completion Certificate” for clients, or a humorous digital badge. You could even post a victory video when your team wraps up each major milestone. It’s about injecting lightness into a time of year that’s normally dreary and stressful.

5. Let your culture shine publicly

Clients and prospects love seeing the real people behind a brand. Post behind-the-scenes office moments on LinkedIn. Show your team celebrating milestones, sharing tips or even just debating which office snack reigns supreme. Personality is contagious when it’s shared consistently and sincerely.

Final thought: be human first, expert second

Pirate Ship didn’t win me over with better postage rates. It won me over because it took a mundane chore like bulk shipping and made it seem fun. The CPA world has just as much opportunity to surprise and delight—without losing an ounce of credibility.

In a sea of sameness, showing a little personality might be the most professional thing you can do to differentiate yourself, your team and your firm.

What is your firm doing to inject more personality into your brand and clients experience?  I’d love to hear from you.

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