Vol. 122 Chewy: The portrait of loyalty 🐾

Case Studied
Rewarding loyalty

Retention is an increasingly formidable challenge for brands across industries. Because of that, we’ve seen brands get pretty creative in their approaches to building it. 

Starbucks and Sephora are known for their highly successful loyalty programs. Spotify Wrapped became a major brand loyalty play for the streaming service. And for years now, Chewy’s surprised customers with custom oil paintings of their pets. 

This week, Case Studied explores how Chewy built customer loyalty with free personalized pet portraits. 

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The Brief

Chewy launched in 2011 with the ambition to marry the speed and convenience of Amazon with the warmth of a local pet store. It grew into one of the dominant forces in online pet supplies, commanding roughly 34% market share in the category. Amazon's share sits north of 50%, which means competing purely on selection or price isn't a long-term game Chewy can win.

Instead, Chewy built its competitive edge around customer service and emotional connection. Its 2,500-person customer service team is trained to answer nuanced pet care questions, from senior dog nutrition to finding local shelters. The company sends handwritten welcome notes to new customers, mails holiday cards to all shoppers, and has been known to send flowers to customers whose pets have passed away.

After seeing success with this philosophy, the brand started taking it a few steps further.

The Execution

Chewy's pet portrait program is an ongoing, in-house initiative that began in 2013, originally conceived by co-founder Ryan Cohen. Each week, Chewy selects customers to receive a free, custom oil painting of their pet. There’s no purchase required, no entry form, and no announcement.

The recipients are typically customers who have a pet photo on their Chewy account or who shared one with a customer service agent during a call. There's no public formula, which is part of what makes the program work: the element of surprise is baked in.

When a customer is selected, Chewy emails a photo of their pet to one of the hundreds of independent artists it works with across the country. Artists like Josh Lawson—who paints between 20 and 50 portraits a week—work from those photos to produce hand-painted oil portraits. 

It can take two or more hours per painting, and Chewy holds the work to strict quality standards. If a portrait doesn't look enough like the pet, it gets sent back to be reworked or rejected entirely. After all, these paintings are essentially equivalent to campaign design assets for the brand.

The finished paintings are shipped directly to the customer, unsolicited, with no accompanying marketing message or promotional insert. 

The Results

The organic lift from the portrait program became clear almost immediately. Customers shared their portraits on social media. Some tweeted at Chewy asking to be selected, while others posted unboxing videos. 

Eric Sheridan, a Florida-based sales specialist, requested a portrait through the Twitter account of his Boston terrier Gozer—which has over 3,000 followers—and received one roughly six weeks later. "Christmas came early," he tweeted from Gozer's account.

Not every reaction is positive, though. Chewy acknowledges that some confused customers return the paintings. But the ones who love them tend to love them loudly, giving the brand a highly shareable, emotionally resonant artifact that lives in a customer's home.

The program's timing also coincided with a period of significant growth. During the pandemic in the August–October 2020 quarter, Chewy's sales increased 45% year-over-year. The company added 5 million new customers in a single year, bringing its total customer base to nearly 18 million. Its stock tripled in value in 2020.

The Takeaways

1) Make the customer experience memorable.

Chewy doesn't compete with Amazon on selection or logistics. Instead, it invests in the kind of personalization that evokes emotions. The portrait program is the most visible example of that, but it's part of the brand’s larger strategy. Handwritten notes, holiday cards, and sympathy flowers all demonstrate personal touches that set Chewy apart. 

Think about the touchpoints in your customer journey that feel transactional and ask whether any of them could be transformed into a more personalized moment. You can start by identifying the emotions you’d want customers to feel in the moment and work backwards from there. Whatever it looks like for your brand, a “just because” gesture can do a lot by way of brand loyalty.  

2) Surprise is a retention strategy.

Part of what makes Chewy’s portraits effective is the fact that they’re unsolicited. If the brand ran a "Submit your pet for a free painting" contest, the effect would be entirely different. The surprise mechanism creates delight rather than expectation.

When designing customer experiences, consider ways to deliver value without the customers opting in or asking for it. It can feel more meaningful to proactively recognize customers through gifts, early access, or milestone celebrations. The surprise signals that you see and appreciate their business.  

3)  Cultivate organic engagement.

After receiving her portrait from Chewy, Annesley Clark took her portrait to a picnic and showed it to all her friends saying, “Look at this. It’s perfect.” She’s one of many recipients who posted their portraits on social media after receiving it, all without being prompted by Chewy. 

Think about what your brand could offer that would make a customer pull out their phone and post about it without being asked. It could be an experience, a piece of recognition, or even a piece of content that’s personalized enough that someone would want to pass it along (looking at you, Spotify Wrapped). 

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