Embracing Scrappiness
In 2015 I became obsessed with the idea of texting to buy a pair of glasses. Launching this product experience led to one of the most humbling and important lessons I’ve ever learned about building a startup.
I was working in ecommerce at Warby Parker, and my job was to grow the Home Try-On business in two ways:
Drive Home Try-On orders and
Increase conversion from Home Try-On to sales
We knew that some of the best ways to increase conversion involved simplifying checkout, and text-to-buy was our newest idea. I learned in user interviews that it was natural for shoppers to use their phones to take photos and send them for feedback. But when they decided on which frames they wanted, almost everyone’s instincts were to place orders on their computers.
“It will be easier to find the pair I’m looking for on my computer than on my phone.”
What if you didn’t have to find the frames again and you could just text us what you want? I wanted to make ordering with your phone as easy as sending a selfie.
I went to work to prove we could do it. I explored the technical requirements for implementing a high-deliverability solution that could reach all customers. I spoke to Twilio and several nascent companies that had built tools on their platform. I scoped how the orders would be placed with the engineering team, evaluated risks with finance and legal, and figured out how to trigger email flows with the data science team. I probed the CX team to understand how much engagement an individual could handle and the brand team about ways to communicate this new service.
In short, I figured out how to offer this innovative solution to our customers, and I couldn’t wait to show my team.
Getting Schooled
The meeting started well. Everyone was onboard with the idea. But as we started talking about next steps, our Co-CEO Dave stepped in with an appeal,
“This sounds good, but it’s going to take a lot of time and resources. Can you launch this with customers for free by Friday?”
Wow.
Here we are, a five-year-old company that has raised over $200 million. We are earning tens of millions of dollars of ecommerce revenue, serving hundreds of thousands of customers, and Fast Company has just named us the most innovative company in the world. Despite all of this and the care we put into building a lasting brand, our CEO was asking if I could launch a janky version by the end of the week.
It was absolutely the right question.
Instead of spending weeks handwringing over Jira tickets, drawing months of resources, and rolling something out to the whole customer base, I started by texting one customer the next day using a free Google Voice number.
Over the next few days, I texted hundreds of customers and developed a better understanding of their behaviors. A teammate from CX took over and soon we were texting hundreds every day. Over time we added people, integrated workflows, and pursued most of what I originally scoped. And by hacking it together, we iterated our way to a full offering, learning about our customers along the way.
This taught me what it means to have a culture of rapid testing and experimentation. Forget about engineering and design resources, I couldn’t even get this idea considered for the roadmap without learning more about how it might perform first. Adding it to the roadmap was a non-starter.
Scrappiness is a Mindset
In the end, text-to-buy didn’t have the impact we thought it would. Customers texted and engagement was high, but it didn’t translate to purchase intent. “Conversational commerce” never took off. Maybe it was because mobile checkout on the site got better or because the company launched a snappy mobile app. But that’s not the point.
Five-plus years after selling the first pair of glasses, we were still grinding out quick and easy tests. Remember, Warby Parker was a well-funded, hyper-growth startup in 2015. We were maniacal about delivering an exceptional customer experience and we had a lot to lose if we screwed things up. We had the capital to add headcount and take big swings. But that didn’t stop us from acting small and scrappy. We made little bets over and over and then piled resources behind the best-performing ideas.
In the new normal of 2023, where capital is difficult to raise and growth expectations for most companies are dampened, you may want to throw your hands in the air and say R.I.P. Good Times. To lament what you could’ve done with more resources.
I’m here to say that maybe these capital constraints will create good times. Airbnb, Stripe, Datadog, Slack and Warby Parker were started in the last recession. These companies were born in capital-constrained environments, and scrappiness persists in their cultures. Airbnb’s co-founders famously sold political cereal boxes in 2008 to fund their business when no one else would. What myriad ways does that entrepreneurial spirit spread through their people?
As startups look ahead into 2023 and beyond, capital efficiency, creativity, and scrappiness are more important than ever. But you shouldn’t just embrace them now in this market. They are distinct advantages in any market. The scrappy creativity that’s forced on you today might be just the thing that sets your business apart tomorrow.