How Ollie cut churn and maximized efficiency

"For a premium brand like Ollie, the experience has to match the product. Gladly was the partner that got us there."

Benjamin Devey
Sr. Director of Customer Experience, Ollie

The challenge when tickets kill relationships

Here's what keeps subscription CX leaders up at night. A customer emails on Saturday evening about their dog food order saying they want to cancel. Maybe their dog didn't love the new recipe. Maybe a box arrived partially thawed. Maybe they're just overwhelmed and need someone to walk them through adjusting their delivery schedule.

You find out Monday morning. By then, they've already cancelled. The moment to save that relationship has passed.

For Benjamin Devey, Sr. Director of Customer Experience at Ollie, this wasn't theoretical. When he joined Ollie in 2022, he walked into exactly this scenario playing out dozens of times a week. The premium pet food brand was delivering personalized, human-grade meals to thousands of dogs nationwide. Every recipe customized down to the calorie. But their customer service? Built on a platform designed for tickets, not relationships.

"Even with connectors to our ecommerce platform, you had to hope that tickets were related to the same customer. If someone sent an email and then an SMS, those were completely separate conversations. Our team had to play detective just to understand what was happening."

Benjamin Devey
Sr. Director of Customer Experience, Ollie

The cognitive load was crushing a lean team of 20 "Canine Care Advocates." Worse, the platform couldn't identify high-value customers automatically. A subscriber spending $200 monthly got the same generic queue as someone on their first order. For a business where lifetime value determines survival, this wasn't just inefficient. It was existential.

And adding the channels customers actually wanted? Chat, SMS, proactive outreach? That required expensive enterprise upgrades and engineering resources Ollie didn't have.

"I would have to update to their enterprise product and need internal resources to do something," says Devey. "I got it out of the box with Gladly."

The solution focused on putting people back at the center

Devey had seen this problem solved once before. At his previous company, he'd led the switch from a ticket-based platform to Gladly. He knew what good looked like.

So when he joined Ollie and saw the same broken system, he made a bet. Give me three months and I'll show you what customer-centric actually means.

"I felt really confident going in that Ollie wanted to make our customer experience a point of differentiation both from an acquisition standpoint as well as retention," Devey explains. "It was a no-brainer to come in and make the same choice."

The philosophical shift was deceptively simple. Stop organizing around tickets. Start organizing around people.

One customer, one story, complete context

With Gladly, every conversation lives in one continuous timeline. An email from Tuesday, a text on Wednesday, a call on Thursday. It's all there. One customer, one story, complete context.

"With Gladly, everything is under one customer view. It's a game-changer for efficiency," says Devey. "I can immediately look at what those Gladly topics were and have a pretty good sense in just a few seconds what's been the most recent events in this customer journey."

For retention conversations, this changed everything. When someone calls about canceling, agents instantly see their delivery history, recipe adjustments, previous concerns, and lifetime value. Not just transaction data, but the relationship.

"We really wanted to build workflows around high LTV customers and specific use cases, especially being a subscription business. Gladly is extremely easy to set those flows up and make sure that I'm getting those contacts to the right team."

Benjamin Devey
Sr. Director of Customer Experience, Ollie

Meeting customers where they actually are

Within weeks, Ollie added chat and SMS. Not because the platform forced them to consolidate channels, but because it made adding them effortless. The IVR now prompts customers to text instead of waiting on hold. 60 to 80 people take that option every week.

"I'm still a big believer that I don't care how customers want to reach out. It's more about getting to them quickly."

But the real unlock came from proactive chat. Specialists now engage website visitors during the meal plan builder, answering questions about ingredients and portion sizes in real time. The human touch at the moment of doubt.

The result? A 120% increase in new customer onboarding attributed to the CX team.

"I even had someone from growth recently say, 'Hey, this would be a great page for one of your proactive triggers.' So that's when you know they're really bought into it."

AI that knows when to crack jokes and when to just listen

By 2024, Devey knew AI was inevitable. The headlines were screaming about it. His team was worried about it.
So he got ahead of it.

He aligned with leadership first on a three-part strategy. AI to assist agents, AI to analyze data, and AI to handle routine questions so humans could focus on the conversations that actually matter. Then he brought the team in.

"AI was dominating headlines when we launched Gladly AI. We took a proactive approach by aligning with leadership first, then communicating our three-part AI strategy to the team. Being transparent about how AI would fit into our operation prevented the fear factor."

Three team members who were curious about AI got involved in testing. The team named the AI "Astro" after the Jetsons' dog. It felt like theirs.

But here's where it gets interesting. Ollie gave Astro different personalities based on emotional context.
For everyday questions? Astro delivers dog puns that would make anyone groan-smile. The team actually saves the best ones to use themselves.

But when someone reaches out about their dog passing away, about crossing the rainbow bridge? Astro knows to drop the playfulness. To be gentle, empathetic, present.

"We love dog puns for everyday conversations, but for rainbow bridge situations when someone's letting us know their pup has passed, we give guidance to be empathetic and appropriate. We have that level of control over our brand voice."

This is AI that actually gets it. Not a chatbot trained on generic support tickets, but an assistant that understands the relationship between a person and their pet.

The results? Astro now resolves 60% of conversations and handles work equivalent to six additional full-time staff. But more importantly, it solves the Saturday night problem.

"We're not 24/7, so if someone emails about canceling on Saturday night and we don't respond until Monday, they've often already moved on. With Astro responding immediately, we're seeing actual conversations happen and higher save rates as a result."

Turning complaints into quality control

The most sophisticated move Ollie made wasn't visible to customers at all.

Working with their data team, they connected Gladly's conversation topics to order attribution through Snowflake. Now when customers report thawed packages or consistency issues, those complaints automatically tie to specific fulfillment centers and production batches.

They built a dashboard called "Watchdog" that their food product team checks daily.

"Now when we see a spike in thawed packs or consistency issues, we can immediately pinpoint which fulfillment center it's coming from."

Customer service stopped being a cost center. It became an early warning system that protects product quality before small problems become brand reputation issues.

The outcome of growing without breaking what makes you special

Three months after implementation, Devey delivered the results that make CFOs pay attention.

"Gladly reduced our total contract by 15% out of the gate while improving overall contact efficiency by 30%. That makes a leader look really good, showing that kind of immediate impact."

Benjamin Devey
Sr. Director of Customer Experience, Ollie

Retention numbers that tell the real story

But the retention metrics tell the deeper story. Ollie's team now saves 45% of at-risk customers who reach out about canceling. Proactive SMS campaigns reduced churn by 7%. The seven-day vet tech text check-in improved retention by 4% compared to control groups.

The team scaled from 20 to 50 agents while maintaining the personalized, consultative approach that defines Ollie's brand. Astro handles the equivalent of six full-time employees, but it freed humans to focus on the complex conversations that drive loyalty.

"Gladly was a big win for employee experience. When we're focused on reducing agent effort, not just customer effort, we see better retention, higher engagement, and ultimately better customer service. Happier agents make for happier customers."

When CX becomes your best acquisition channel

The unified platform transformed how Ollie thinks about customer acquisition. With proactive chat on the website, CX specialists can now engage potential customers at the moment of consideration, answering questions in real time.

The 120% increase in new customer onboarding attributed directly to the CX team wasn't just a metric. It represented a fundamental shift in how the company thinks about the role of customer service.

"Proactive chat has become one of our main levers for driving incremental growth. We've gotten really bullish on it after seeing how it impacts conversions."

Finding a partner, not just a platform

For Devey, choosing Gladly wasn't just about features. It was about finding a partner who understands that CX leaders don't have unlimited engineering resources or patience for support teams that know less about the product than they do.

"Support's a big deal. I talked to existing Gladly customers before switching, and their support is truly different. With some platforms, I knew more about the product than their support team did. Gladly's people actually know their stuff and help you solve problems, not just point you to documentation."

As Ollie expands into Petco stores nationwide and continues building out their health screening capabilities, the platform scales with them. The roadmap includes expanding Astro's capabilities, but the foundation is already solid.

A system where every customer is known, every conversation is connected, and every interaction builds toward something deeper than a transaction.

"At Ollie, we believe pets deserve human-grade food, and pet parents deserve human-grade service. With Gladly, we've found a partner that shares our philosophy that relationships, not tickets, are what matter most."

Benjamin Devey
Sr. Director of Customer Experience, Ollie

For subscription brands trying to figure out how to scale without losing what makes them special, Ollie's story offers proof. The right platform doesn't make you choose between efficiency and humanity.

It helps you deliver both.