Scrappy customer success at scale Doing more with less at scale

This article is based on a presentation given by Tolu at Customer Success Festival Chicago in 2023.

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Scaling customer engagement across hundreds of accounts has been one of the most demanding yet fulfilling aspects of my work. 

I lead our scaled customer success efforts for Chrome Enterprise – focused on helping customers adopt Chromebooks and manage them effectively using our software.

One question I often get is: Why is someone from Google talking about being scrappy? After all, Google is one of the largest companies in the world, and “scrappy” isn’t necessarily the first word that comes to mind.

I get it. Many of you reading this have been operating scrappily for years, often out of sheer necessity. But over the past two years, I’ve had to get creative with limited resources, and it’s taught me a lot about how scrappiness can yield surprising results.

What’s more, I’ve learned that the principles of scrappiness shouldn’t be abandoned, even when you have access to greater resources. Sometimes, thinking of yourself as a big corporation – or leaning too heavily on the resources that come with that – can actually slow you down.

In fact, embracing scrappy thinking can accelerate progress and open new opportunities.

If you’re after polished stories and tactics about flawless execution or guaranteed success, then I'm sorry this article isn’t for you.

But what these authentic stories show is the payoff you get from scrappy, resourceful strategies is attainable to everyone. Hopefully, you’ll find some inspiration in them for your own work.

Let’s dive in.

What does it mean to be scrappy?

Before diving into my experiences, I think it’s important to define what being “scrappy” actually means. 

Everyone seems to have their own take on it, so I turned to a classic source: Dictionary.com. According to them, “being scrappy” means “having or showing spirit and determination, especially in spite of obstacles.”

This definition is a great starting point, but there’s another definition I like even more, one I came across in a book by Kimberly Wiefling, Scrappy Women in Business (2010).

The book includes a variety of takes on what it means to be scrappy, but the one that resonates with me the most is this: “EDGY!... and is your edge in achieving outrageous results even when they seem impossible.” That sense of possibility, even when the odds are stacked against you, feels central to my own experiences.

Why did some results feel impossible in my context? I’ll get to that shortly. But first, let’s unpack how this spirit of scrappiness can lead to outcomes that defy expectations.

Setting the stage: The obstacles we face

At the Customer Success Festival in Chicago, I asked the room of professionals: “What corporate device are you using?” A show of hands revealed that the majority of the audience use Windows devices, followed closely by MacBooks.

And then I asked: “Who here is using a Chromebook?” Maybe one hand went up; two at the most. That’s the challenge right there.

When you’re championing a challenger product in a space dominated by well-loved, established options, getting people to adopt your offering is an uphill battle. It’s not that people dislike Chromebooks – they just love what they already have. 

Convincing them to try something different requires overcoming significant inertia. That’s obstacle number one.

Next, I asked: “Who here manages or is responsible for at least 50 customers?” Hands went up. Then I ask about 100, 500, and even 1,000 customers. The higher the number, the fewer hands remained raised. For most, managing fewer customers was the norm.

Now, let’s go back two years. I accepted a role with the mandate to engage and improve the experience for core enterprise-scale customers. My task was to identify challenges, determine opportunities for improvement, and build a small team – maybe three or more people – to execute this vision.

But shortly after starting, the landscape shifted. Like many companies at the time, ours froze hiring and halted additional resource allocation. Instead of building a small team, I found myself in a one-person team responsible for supporting 800 customers. 

And these weren’t just any customers – they were enterprise-scale businesses, tasked with adopting Chromebooks, a product we just established as notoriously difficult to get people excited about.

This was the moment when scrappiness became essential. How could I get 800 different customers not only to adopt but to feel genuinely enthusiastic about something that, in a room full of professionals, no one else was adopting? This challenge was where my journey into scrappy solutions began.