How to Lose a Customer 💔

If you follow me on LinkedIn, you might have seen this post about my beloved Shasta that recently passed away. Shasta was with us for 12.5 years. She wasn’t just our dog. She was the heartbeat of our home. The grief that followed her passing was the kind that hits you in waves, at random moments, at Whole Foods, in the car, on a walk, at nighttime, really everywhere.

When I posted about her passing on LinkedIn, the response was overwhelming - in the best possible way. Hundreds of comments. Dozens of texts, DMs, emails. People from across the pet industry and beyond saying “I know this feeling,” “I’m so sorry,” “Let me know if you need anything.” Some I’ve never met, reaching out like they’d known us for years. That kind of human response in a moment of grief is something you don’t forget.

Which is why the following response to the cancellation of our Ollie subscription felt insensitive. When my wife went to cancel our 6+ year subscription for Shasta, putting the reason for our leaving as the passing of Shasta, we got this automated generic response. The wound was still fresh, and honestly, it felt kinda shitty.

We had been Ollie customers for more than six years, with only a few short breaks in between. That's not a casual customer relationship.

After Shasta passed, my wife went to cancel our subscription. When the system asked for the reason (via a multiple-choice menu), she selected the option Ollie itself provided: the loss of a pet.

In response, the above was the automated email she received.

It confirmed the cancellation. It thanked her for being part of the pack. And then, at the very end, it told her to "give Shasta an extra belly rub from us."

Shasta had just died.

I understand automation; I know how email flows are built, how cancellation sequences get triggered, how teams set these things up once and move on. But here's the thing: when you give customers the option to tell you why they're leaving, and one of those reasons is the death of their pet, you've introduced a piece of information that demands a response with zero room for error.

I sat on it for a few days, but eventually, I decided to post about it. I thought it was something that needed to be addressed, and because I believed, as someone who covers this industry, that there was something worth learning here. See post here.

What Happened When I Posted

The response was immediate and, again, overwhelming. People from inside and outside the pet industry chimed in. Pet parents who'd experienced the same thing - automated reminders about a dog who was gone, upsell emails sent to recently grieving customers, vet clinics sending wellness check-ins for pets that had passed.

It turns out that the administrative reality of losing a pet - the cancellations, the notifications, the systems that don't know yet - is a kind of grief that almost nobody talks about.

Here are a select few comments:

Britta Mulderrig, a founder building the future of pet loss grief support, commented on the post: after losing her dog Jasper, "canceling his food, supplements, medication, and pet insurance was brutal in a way I didn't expect. After 15 years of my life revolving around him, everything just stopped."

That's not a niche experience. That's universal. And multiple people pointed out the obvious: if your system is sophisticated enough to offer a dropdown that includes "my pet passed away," it is sophisticated enough to route that cancellation to a different flow entirely.

Ollie did respond. Their brand account left a comment acknowledging the failure, saying this was not how they handle the passing of members and that they would be in touch directly. Nick Stafford, the CEO, also commented — speaking to the heartache his team genuinely feels when a member of their community passes, and the protocols they take seriously. I thought that was genuine, and the fact that he personally commented, I thought, was important, the right thing to do, and I really appreciated it.

Giving the Benefit of the Doubt

When one commenter asked me directly whether the belly rub email was intentional or an error, I replied honestly: according to them, it was an error in their system. I've spent enough time in and around this industry to know that building and maintaining customer communication systems is not simple, and that gaps happen, and that the size of a company does not always protect you from a missed edge case.

A few hours after I posted, someone from Ollie reached out to my wife directly. They apologized and said that if we needed anything, to let them know. It was a kind gesture, though I'll be honest: it felt a bit scripted. But in a moment of reactive damage control, scripted is still better than silence.

Shortly afterward, flowers from Ollie arrived with a condolence note. It was a thoughtful touch and, for the first time, brought a sense of humanity to what had, up until then, felt like a largely digital experience.

They also noted that they had made a donation in Shasta's memory.

Here is what the note said:

“Dear Rumika, on behalf of everyone at Ollie, we are so deeply sorry for the loss of Shasta and truly heartbroken that our automated email added any pain to your grief. Thank you for allowing us the privilege of being a part of her life. To honor her memory, we are sending a donation in Shasta’s name to Marley’s Mutts Rescue".”

Chewy set the blueprint

In the comments, Chewy came up again and again. This is well-trodden ground in the pet industry, but it bears repeating because the underlying principle still matters.

Chewy has built a reputation for showing up when customers are going through one of the hardest parts of pet ownership. Flowers, handwritten cards, unsolicited refunds, thoughtful gestures - stories like these have circulated for years. They've become part of how people talk about the company.

Can smaller brands replicate that?

One commenter made a fair point: Chewy is a massive public company that spent years investing heavily in customer experience and had resources that most family-owned businesses simply do not have. That's true.

But the lesson isn't that every company should send flowers. The lesson is that grief is a moment that reveals who you are as a business.

Empathy doesn't require a million-dollar customer service budget. It requires paying attention. It requires intention. A thoughtful note, a sincere message, a waived fee, or simply knowing when not to sell can leave a lasting impression.

The specific gesture matters less than the mindset behind it.

As the comment below explains:

I saw that same intention in a gesture from Trees for Pets founder Marlen Farley, who reached out personally to let me know they had planted a tree in memory of Shasta.

I didn't ask for it. I certainly didn't expect it.

The tree itself mattered, but what mattered more was the thought behind it. Someone saw my post, recognized what it represented, decided a gesture was appropriate, and took the time to act on it.

That's the human touch.

It's not about the cost. It's about noticing. It's about caring enough to do something when there is nothing to gain from doing it.

And that's precisely the thing automation cannot replicate. By definition, genuine empathy requires a person on the other side making a conscious choice.

On Saying Goodbye the Right Way

I want to talk about one more thing, because it's not separate from the rest of this.

Three years ago, I lost my other dog, Tako, at 16. We went to the veterinary clinic. And I'll be honest: it was traumatic. Maybe because I didn't know what to expect. Maybe because he'd been with me through my entire adult life. But it felt clinical. It felt strange to leave him there afterward as we left. I walked out feeling like something important had been mishandled, even though nothing technically had.

With Shasta, we used Lap of Love. It was different in every possible way. She was in her bed. She was at home, surrounded by people who loved her. It was quiet, and calm, and felt like what it actually was: a goodbye.

I genuinely believe it is the only way I would ever do this again. Not because the clinical alternative is wrong, but because there is something about a dog leaving in the place they felt safest that feels like the dignity they deserve. If you've never heard of in-home euthanasia, or dismissed it as not for you, I'd encourage you to reconsider. It made one of the hardest moments of my life bearable in a way I didn't think was possible.

Automation isn't the enemy here. Automation that ignores its own data is.

If you are a pet brand that collects cancellation reasons, and one of those reasons is pet death, you have two options. One: do not offer that option at all if you are not prepared to respond differently to it. Two: build a separate flow. Route that to a human. Pause every automated follow-up in that customer's journey. Flag the account. Give someone on your team the information and the instruction to act like a person.

The cost of doing that is not high. The cost of not doing it - in customer trust, in public perception, in just basic human terms - is.

One last thing I’ll add: around the same time, I received a cold pitch from a founder I've never spoken to before with the subject line: "We Make Euthanasia Less Suck."

I know, great headline. Clearly, this founder is still learning how to use AI, but the email was tone-deaf and unnecessary. I genuinely do not understand treating a moment of grief as a sales opportunity.

Where We Land

Ollie sent an email that landed badly in the worst possible moment. They responded, eventually, with some level of genuine acknowledgment. Flowers arrived. The CEO responded. Whether any of that wins back a customer in the long run, I honestly don't know; time will tell. What I do know is that reaching out to a long-time customer after a mishap is the only way to remedy it, and overall I think Ollie did a pretty good job.

The human touch in a world of automation isn't a feature. It's a differentiator. The brands that figure that out - not performatively, but structurally, in the way they build their systems and train their teams and think about the moments that actually matter to their customers — are the ones that earn the kind of loyalty that doesn't show up in churn models. It shows up in the stories people tell.

Shasta was the best of us; I know everyone says this about their dogs, but Shasta really was. A quiet confidence, a pure heart; she loved all, purely & unfettered.

I hope heaven is filled with tennis balls. RIP Shasta; we miss you forever.

One final note: if you are dealing with pet loss, Love Baxter is an amazing resource.