Shippo Leadership Q&A: Onward with Catherine Stewart

When last year’s search for a new COO began, our CEO Laura wanted to find a partner to help her run and grow the business — someone who knew how to design and structure an organization that could scale to 1000 people and up. Enter: Catherine Stewart.

Prior to joining Shippo, Catherine was the Chief Business Officer at Automattic, the company behind WordPress.com and WooCommerce. As CBO, she focused on putting the people and processes in place to enable the company to rapidly grow. Catherine joined Automattic in 2014, when the company had ~250 employees and a valuation of $1B, and helped grow the company to 1300 employees and a valuation of $3B. During her tenure, Catherine helped the company QUINTUPLE their revenue.

A few weeks before Catherine’s official start at Shippo, we connected with her over Zoom to talk about her time at Automattic, and hear how she plans to use her experience to tackle Shippo’s challenges. As members of the Shippo team joined the call, our recruiter Alvin unintentionally connected as a potato due to a zoom filter mishap. Catherine calmly provided potato-reversing guidance, tackling her first challenge at Shippo before even officially joining the team. Talk about first impressions. Here are some highlights from the team’s conversation with Catherine.

What did you do at Automattic? How did it prepare you for Shippo’s challenges?

When I joined, Automattic’s founder and CEO, Matt Mullenweg, asked me to “think about the money so that others wouldn’t have to.” 

What that meant on the ground was that every six months, my job felt completely different. What makes a growing company successful over the long term is adaptability, willingness to grow, and change. Change is never comfortable, but what takes a company from zero to $5M in revenue, from $5M to $20M, from $20 to $100M, and from $100 to $750M are different. 

What got you here, won’t get you there. The ability to adapt and embrace change is paramount to navigating these transitions well. I joke that my career has moved in reverse, because I’ve often joined companies that are on a path to becoming the size of the company where I just was. Having seen tech companies navigate different stages of growth helps me anticipate the scaling challenges we’ll encounter as we grow to $1B+ in revenue. 

What did you enjoy most as CBO?

I love working with teams. Helping people do more in their roles, clearing roadblocks, growing into a new role or a new level within their function is deeply gratifying. Aside from the day-to-day — when you build a better product, and help people find it — you help your customers succeed. 

Long story short, I’d say the people component on both sides — the team members and the customers — is where the greatest job satisfaction comes for me.

How would you characterize the way you like to work and communicate with employees and team members?

I like to have an open door so that people feel comfortable reaching out, even if they’re not team members or they don’t have regular interactions. I try to be as open as possible to feedback because I think it’s always valuable. 

What excited you about Shippo and the opportunity today, and why did you think now is an interesting time to make a career change?

I’d been at Automattic for close to six years, so it was less about leaving Automattic, and more about the excitement of Shippo’s opportunity. I met Laura back in 2015, when Woo was considering changing shipping partners, and was impressed then. In the years that followed, Shippo’s growth on Woo’s platform was impressive. When we were reconnected in 2020, I loved her vision. And ever since my days at Random House, I’ve had a soft spot for supply chain. 

As Laura has said many times, Amazon has changed the expectations in consumers’ minds, especially in the US. It’s redefined what a good experience looks like, how quickly a customer should receive that item, how reliably, how easy it is to track, and what it looks like when you open it. Amazon does not make that experience special or tailored, though, and there is an increasingly large number of small businesses that want to use the shipping opportunity as a chance to turn a first purchase into delight followed by long-term loyalty. 

A change like this is a significant opportunity. Right now, finding the best shipping solution is hard. Small businesses don’t have a lot of time to wade through the different options. I think there’s a tremendous value that Shippo can bring to people’s everyday lives. And if we do this well, then the sky’s the limit.

Just For Fun: What do you like doing outside of work?

With the current shelter-in-place, the world feels more limited. So, my husband and I are enjoying cooking. We just started growing some basil and it grew awfully high so I made pesto last night. I’m not cooking from Ottolenghi, or making cheese souffle, but it’s just been nice and relaxing at the end of the day. [Update: Since the end of covid, we now are cooking from Ottolenghi; I’m happy to report that our skills have improved!] I love books; I worked in publishing for a reason. I was an English when I was in college, and I love moseying around libraries and old bookstores.

What’s your favorite restaurant in San Francisco?

I like neighborhood places. Delfina Pizza is one of the first places I ate at when I came out to San Francisco. My brother, who lives in SF, took me there when I flew out for my Facebook interviews. It was part of his long-standing plan to convince me to move West, and it worked.

Are you interested in working with Catherine and/or at Shippo? Be sure to check out our job listings here: /jobs/