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Catherine Stewart: My Simple (But Very Effective) Tactic for Emotional Connection

June 1, 2020
Sheena Badani

Sheena Badani

Revenue Intelligence

How can you still grow fast while building Sales and Marketing teams from scratch?

What are the advantages of either an in-person or remote workplace?

Is relying on remote work tools inevitable, even for in-person companies?

On a recent episode of the Reveal podcast, we connected with Catherine Stewart, chief business officer at Shippo, for answers to these and other questions that are top of mind for revenue leaders.

Key Points to Remember

  1. Don’t penalize employees who are exceptionally efficient, simply because they’re only working five or six hours a day.
  2. Success never comes from one person. It’s the result of great teamwork.
  3. Sales is part of everything you do throughout your entire company.
  4. Having a sense of where your team is at emotionally, as well as in their work, is important.
  5. Newer technologies like Slack or Zoom, even for companies that are not trying to be remote, are becoming increasingly important.

Building Sales and Marketing at Automattic

When I joined Automattic, it wasn’t so dissimilar from Facebook in that the philosophy was, “We should create a great product, something that customers love—and the money will come. We’re not sure how, but we think it will.” 

There was no Sales team. There was no Marketing team. There was some thinking that went into pricing, but nothing particularly structured. There wasn’t any A/B testing. There wasn’t any consumer research. We didn’t have any business intelligence or business operations. We didn’t have any Partnership teams. 

There was a lot of opportunity that we weren’t taking advantage of because we hadn’t made those investments. The company was very focused on engineering. So there was a lot of room. The first thing I did was put in place OKRs and just overall company goals, so that we could all make sure we were running in the same direction. 

The second thing I ended up doing was actually something I had not expected at all, which was M&A. We wanted to get into the ecommerce space, and we didn’t currently have a great solution for our customers. We knew that a lot of WordPress users wanted to also start an online store. We had integrations with a few other startups that provided ecommerce platform functionality. But we felt that it was important enough that we wanted to own it ourselves.

So we ended up purchasing an ecommerce platform called WooCommerce. It’s now our second largest division in terms of revenue at Automattic. So I think that ended up being a good call. 

And then after that, starting up Marketing, Partnership, Inside Sales, and a variety of other teams and functions that would allow us to better execute and monetize the great products that the engineers had already built.

We [Automattic] are still fairly focused on marketing as the priority. We do have inside sales. We’re doing a lot of that through a third party. We do also have enterprise sales, but it’s a relatively small team given that we have so much inbound interest, we haven’t needed to do a lot of proactive sales. 

I don’t want to penalize an employee who’s exceptionally efficient because they’re only working five or six hours a day. If they’re able to get their job done to a high standard on five to six hours a day, congratulations. Power to them.

Succeed as a Team

I love building teams because I like the creation of something new. I think there’s so much satisfaction that comes from when you build something that hasn’t been there before. And then you get to see it work. 

So for example, with Partnerships at Automattic, it was pretty exciting—within maybe a year of hiring that team—to see that it was already contributing to somewhere between 15-20% of the revenue. Which for a team that’s only been in place for a year, I think is something to really be proud of.

And what I think is most important is acknowledging that those achievements will not come from me. I’m just one person. I can put the right processes in place, and I can try to put the right people in place. Figuring out the right match between each person and what needs to be done at the company, and making sure that we’re making good hiring decisions. Those are the things that I can contribute. 

But ultimately, the success is the success of the team. And I’m really excited to join what’s already a great team at Shippo, and see how we can together take the company to the next level.

I think that sales is not just limited to sales teams. Sales is a part of absolutely everything we do, and almost every part of a company.

In-Person vs Remote Work

In-person I think is preferable for developing a relationship and establishing trust, because you get so much more information when you’re seeing someone face-to-face than you do when you’re hearing their voice, or when you’re getting a Slack message from them. I think it’s almost a hierarchy in terms of how much information you’re able to pick up from that particular interaction.

And while there’s so much value to Slack and to text-based communication, there’s so much value to long-form communication that keeps track of meeting notes, and decisions to be made, and strategic plans. There’s a time and a place for all of this. But I do think that onboarding, and meeting a new team, and developing new working relationships, is best done in person. And so what I’ll try to do is mimic that as much as possible. More Zoom calls, at least to start, so we can get a feel for where we all are. 

When you’re remote, you don’t get the same chit chat before the meeting starts. You don’t get to see how your colleagues are feeling. So something that a career coach told me to do is kickoff check-in meetings—weekly team meetings for example—with something called green, yellow, or red. 

So people will quickly go around the proverbial Zoom room and say, just in a minute or two, “I’m Green. My weekend was great! Very excited to kickoff this Monday. I have a lot of work that I can’t wait to dive into.” Or they might say, “Actually, I’m red because this deal has been going sideways. Not really sure how to handle it. It’s really been on my mind.”

I just feel that, particularly now, there’s a lot of anxiety. There’s a lot of change. We’re all doing our best, but having a sense of where your team is at emotionally, as well as in their work, is important. 

I think [remote work is] not only useful for hiring and for retention, but it’s also inevitable in some ways. So Facebook…was all about, “We want people here as close as possible, ideally in Menlo Park. We’ll accept commuters from other places in the Bay Area, but we will not be opening an office in San Francisco. We’ll have an office in New York for any sales reps that need to be close to clients. But we don’t want engineers there.” Same stance on London.

The goal was to find great people who would then be willing to relocate to Silicon Valley, or to hire locally. And at some point though, that doesn’t scale. Everything stops scaling at some point. So I’m not just saying that in-person stops scaling. There’s certainly challenges to scaling remote environments as well.

But certainly at Facebook, it’s already well beyond the point where the standards were starting to relax a little bit in terms of, “Okay, fine, we’ll let engineers work in New York because there’s so many who want to, that we’re really missing out if we don’t make that possible.” And, “Alright, we’ll allow there to be an SF office.”

But practically speaking, even if you’re in Menlo Park, a lot of your meetings will have to be over Zoom anyway, because it takes so long to get from one meeting location to another. We’re talking about a massive campus at this point. Not everyone can afford to take 20 minutes in between meetings to get from one to the next. It’s just inefficient. 

So, I think that what we mean when we say remote is starting to change. And that a lot of newer technologies like Slack or Zoom, even for companies that are not trying to be remote, are becoming increasingly important.

The main advantage [of remote work] is the flexibility and the geographic opportunity, in terms of being able to attract and retain really talented employees. 

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