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Catherine Stewart on Scaling Ops at Shippo and Automattic

Jan 19, 2022 · 33 min read

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Catherine Stewart is the former Chief Operating Officer at Shippo and Chief Business Officer at Automattic (WordPress),  joins us in part one of a special two-parter, to talk about the craft of scaling operations at hyper-growth tech companies. Topics include shifting strategic priorities at Automattic to also focus on revenue generation and e-commerce through the acquisition of WooCommerce, the shift from Facebook to Automattic, balancing the entrepreneurial mindset with the need for processes, not sugar-coating it, and why her time at Random House yielded some of the most valuable learnings of her career.

Part two, coming next month, focuses on scaling the go-to-market and creating $B's in value.

Shippo is a shipping software company backed by Bessemer and D1, where she led Marketing, Sales, Business Development, Customer Success, Customer Support, People Ops, and Strategic Planning. During her time at the company, Shippo's revenue grew 3x faster than the US eCommerce shipping market, and the company's valuation grew from $220M to over $1B in just 18 months.

Prior to joining Shippo, Catherine was the Chief Business Officer at Automattic, the company behind WordPress.com, during the company’s growth from a valuation of $1B to $3B. While at the company, she led the acquisition and integration of WooCommerce. Previously at Facebook, she helped launch the Facebook Audience Network and led the three-year planning process, and at Random House, worked on the transition from physical to digital books. Catherine began her career as a strategy consultant at McKinsey.

Topics Covered

  • Introduction and Catherine's track record (0:08)
  • From McKinsey and publishing into tech (1:07)
  • Go-to-market passion over finance (3:24)
  • What drove Shippo's outsized growth (4:53)
  • First 30 days and the listening tour (6:17)
  • Change management and Automattic's monetization shift (10:35)
  • Regrettable versus non-regrettable attrition (14:54)
  • Hiring quality during hypergrowth (17:38)
  • Defining the COO role with the CEO (22:25)
  • Recycling playbooks and org structures (25:10)
  • Cherry-picking lessons from Random House and Facebook (27:15)
  • Mentor advice and the Audience Network launch (29:29)
  • Tiger teams balance innovation and process (34:24)
  • Advice for COOs joining a new company (39:26)
  • LinkedIn: https://www.linkedin.com/in/catherine-stewart-800b841/
  • Website: https://catherinetaylorstewart.com
  • Episode Webpage: https://www.betweentwocoos.com/catherine-stewart-part-one-people

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About Between Two COO's

Hosted by Michael Koenig · betweentwocoos.com · b2coos.com

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Full Transcript

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Michael Koenig: Between Two COOs is a podcast where phenomenal chief operating officers from all sorts of companies come to share their insights, advice, and crazy stories. Hello and welcome to Between Two COOs. I'm your host, Michael Koenig, and I'm excited to welcome our guest, Kathryn Stewart. Former Chief Operating Officer at Shippo, a software company delivering amazing shipping experiences for e-commerce businesses, which I can attest to as a former customer. During her time there, Shippo grew 3 times faster than the US e-commerce shipping market, and the company's valuation grew from $220 million to over $1 billion in just 18 months. Prior to joining Shippo, Catherine was the Chief Business Officer at my alma mater Automatic, the company behind WordPress. And prior to Automatic, she was at Facebook helping launch the Facebook Audience Network. Welcome, Catherine. Thanks for being here. I'm really excited to have you on.

Catherine Stewart: It's a pleasure being here. Thanks for having me.

Michael Koenig: Yeah, absolutely. So I always love to start this off. What was your path? How did you end up as COO at Chippo?

Catherine Stewart: Um, let's see. Sort of hard to know where to begin. I think I started my career as something of a generalist because I was at McKinsey. Funny story is I'd actually applied to work in publishing, but my first offer was from the Oxford University Press for $16,500, which was a standard salary at the time in New York City, and realized that that would be really hard to live on. So I decided to work at McKinsey and figured I could always come back to publishing, which I actually did end up doing. I came back to publishing on the business side, but that's how I ended up at McKinsey. And then at McKinsey, I learned really how to sort of swoop into a company's operations and figure out how we could make improvements, try to increase revenue or decrease costs. I ended up working on a project for MySpace, which was my first introduction to tech. That was back when MySpace was actually bigger than Facebook. I also worked on Pfizer clinical trials, to give you a sense of the diversity, and actually just participated in a Pfizer clinical trial. My son was a test baby for the COVID vaccine. So that came full circle. I knew a lot about how they run their trials. And then, yeah, so that was the very beginning of it. And I sort of stayed a generalist throughout. When I was at Facebook, I wore a number of hats from product management to marketing to even worked on the finance side. That's actually how I joined the company, worked on the 3-year plan and a variety of things that ultimately made it such that when I met Matt, Matt Mullenweg, who both you and I worked for back in the day, he said, look, I need somebody who can worry about the money so that the rest of us don't have to. And it seems like you might be a good person to do that. Would you, how would you feel? And ultimately ended up joining the company in sort of the commensurate jack of all trades role, which is COO, CBO, or CRO, whatever you want to call it. And, and started working for Matt. And then the rest is, is a history of 7 years of working at Automatic and then Shipbound.

Michael Koenig: Fantastic. And not only do you have finance experience, but you work a lot on the go-to-market side as well. Would you say that one is a bit stronger than the other? And also, for those COOs out there, Did having a strong finance background help you in other areas?

Catherine Stewart: Yeah. Um, I have to admit that my passion is not in finance. I, whenever I'm asked if finance is a division that I would like to report into me, the answer is usually no. Um, that I will do it if I need to, but I prefer to work with a partner, um, who can essentially be a buddy to me as opposed to, um, It's just not my passion. That said, I have run finance teams on a few different occasions, and so I can do it. I'd say that my passion is much more on the go-to-market side. I love things that you can measure in dollars and cents, and building things that will generate long-term sustainable revenue. So not just revenue this year or this month, but how can we build a business that will be productive and be healthy and sustain the rest of our growth trajectory for the longer term. And so that's the marketing, the sales, the customer success, the, the business development and partnerships, and then anything that's directly supportive of that, like customer support or sales ops, biz ops.

Michael Koenig: Fantastic. And of course, as I mentioned during the intro, the business at Chippo grew 3x faster than other e-commerce businesses in the US. What was some of the success behind that? What drove that?

Catherine Stewart: Well, at the time when I joined Shippo, COVID was just beginning to change the way businesses were operating in the US and abroad. And that meant that there were tremendous opportunities for us, but also real challenges. For example, it's a good problem to have, but when your number of customers doubles or triples overnight, you can imagine what happens to your customer support tickets, to your product's ability to handle that kind of volume, and the likelihood that certain things might break or go down. And so it became a real operational challenge to make sure that all these teams were able to absorb that volume and then keep it, retain it, as opposed to having people come in and test out your product and then turn on to another solution. So, I'd say that the growth that we achieved during that time was certainly partly fueled by COVID, but the growth that we achieved over the market, I think, had to do with building and maintaining a tighter ship to make sure that we were providing a good experience for our customers.

Michael Koenig: That's quite interesting. And you went into this new role as a Chief Business Officer coming from Automatic, a lot of sounds like a crossover between the two roles. In terms of that growth experience at Shippo, when you came into it, how did you evaluate what maybe needed to get tweaked a little in order to sustain that growth and make sure the wheels don't come off the bus?

Catherine Stewart: This is where I probably betray my DNA as an operations person, but I really like to get into the weeds of the company and hear from employees and hear from customers. And so my first 30 days at the company was mostly a listening and learning tour where I spoke with— I think I had at least 50 interviews over the course of about 3 weeks. So it's just one after another after another where I was talking to, um, mostly employees but also customers and hearing directly from them what was working and what wasn't. And then layered onto that, customers who were not currently ours, but were either prospective or customers of a competitor, and then learning why they had selected a solution that wasn't ours. And through that, learned a fair amount about where we were strong and where we were quite weak, and took that to the board. Um, and share those, um, those learnings and also my, my own plan. And I set goals for myself as well where I said, okay, here are all the things that I've heard distilled into ultimately 5 themes to correct these issues or to take advantage of the opportunity that we have. Um, here are the actions that I personally am going to be taking, and here's how I'm going to measure that success. So in 6 months or in 3 months, here's what you can judge me on, right? So one thing that we actually had that I won't go into too much detail on, but we had a fair amount of employee churn at Chippo. And so one of my goals was to reduce that. And reducing employee churn is not something you can do overnight. It takes a fair amount of time and it's a fuzzy thing. Ultimately, the output is highly quantitative and measurable, but what's leading to that churn. And what you can implement is something that's a little bit trickier, takes a little bit more time, but I still had a 3-month, 6-month, and then the 12-month goal was the most important one because a lot of these initiatives would take a little bit longer to deliver, um, and to see the impact. So regardless of what the issue was, there was usually something quantitative along with a set of initiatives, um, that I was holding myself to. And after that board presentation, I actually made the same presentation to the company. And said, hey, I made it a little bit higher level, took it out of the weeds a little bit more, but told the company, hey, here's what I've heard from you. And by the way, after this all hands, if I got something wrong, please let me know. But here's what I'm planning to do, and this is how you can keep me honest, and this is my commitment to you. This is what I'm doing to improve. And I think that's a pretty nice transparent way to Let people know what your priorities are because they're only real priorities if you can talk about them. And if I want other people to hold themselves accountable to particular KPIs or metrics, I need to do the same thing for myself. And I need to be honest if I thought we'd be somewhere in 6 months and we're actually not there. That's something that I need to be quite transparent about, not pointing any fingers, not, but, and certainly not find a scapegoat. But it is something that I want to make sure I'm public about and I'm talking about openly and I'm learning from so that other people will also do the same thing. Because ultimately people don't do what you tell them to do. They do what they see you doing. It's sort of the same thing as you often hear in parenting conversations. So I'd say that was, that was one of the most important things I feel that I did in my first 90 days at Chippewa.

Michael Koenig: It's such a great introduction to the rest of the company to put a face and a voice behind the name of COO, which can be sometimes a little unnerving when a new COO comes into a company, at least for the rest of the team. This sounds like a really great step in removing those nerves. I imagine that there was a lot of change as well. How did you go about some of the change management and how would you have done it differently, perhaps?

Catherine Stewart: Yeah, I think the first thing that's important about change management is acknowledging where you are. I think a lot of companies are tempted to sugarcoat the situation and the status quo. That said, employees know they're there on the ground. If you try to tell them that XY

Michael Koenig: And how did it go? How was it received?

Catherine Stewart: There was a very vocal minority of detractors, but they were a minority. But ultimately, um, I think most people were really excited to see that kind of change, were really excited and had felt that that change was needed for, for some time. And ended up with like little pockets of people within the company who said, hey, this is, this is a fight I really want to get behind, how can I help? And, um, And I think it's valuable to have those public minorities and detractors. It's good to have debate within the company, but ultimately, you do want people pulling on, you want people rowing in the same direction. So if ultimately after a few conversations, it felt like some people were sufficiently unhappy with the company's priorities, that they could no longer be productive, then ultimately it may not be the right place for them. Now, did that happen overnight? Like, absolutely not. And if people privately disagreed but were producing great products, then that was fine too. You know, you don't have to have everybody exactly on the same philosophical page, but if people really felt that, you you know, the company's strategic push into e-commerce was anathema to what they wanted to do for a living, then, um, ultimately e-commerce was a strategic priority for us, so maybe it wasn't the best fit longer term.

Michael Koenig: So you start to get some of that natural turnover that happens when new strategies or initiatives are put in place and prioritized. The turnover itself though, outside of just the person leaving, can be quite disruptive for the rest of the team. How do you help your team maintain focus and also confidence when they see some of their peers leaving the company?

Catherine Stewart: It's a great question. It's one that's been top of mind for a while. So, Automatic's level of attrition was very low, very low. Chipos was quite high. So you always want to be measuring against the baseline, and the baseline is something that is sort of available based on talking to VCs who work in your industry and other COOs or CEOs. And, um, in tech it's probably a bit higher than in other industries, but if you have 40 to 50% attrition, I call that high. And if your attrition is 4 to 5%, I'd call that low. Um, and I think that it's more than just what is the attrition rate, but how much is regrettable versus non-regrettable. And some people measure it more in terms of voluntary and involuntary, which I think is also a useful metric. It tells you different things. It tells you about the effectiveness of your hiring versus, you know, how much people want to stay and continue working at your company. But regrettable versus non-regrettable, I think, is the more meaningful metric to look at. And ultimately, you don't want to keep people who are underperforming for whatever the reason, whether it's an attitude issue or it's a work ethic issue, or they are not at the level of quality that you need from that engineer or from that marketer or whatever the role is. Keeping that person around for too long is actually quite demoralizing to the people you want to retain the most, to the, to the A players, the people who are working really hard to make the product better, to make the experience better.. And I think that it's just as damaging to have people staying too long who have, who are not a great fit for the company as it is to have people stay not long enough. And when they don't stay long enough, particularly if you're talking about the A-players, then that's a different problem. And that's a really important one to solve because naturally your company is only as good as the talent that it employs. And turnover can be very disruptive, as you pointed out, but a certain amount of turnover, I think, is also necessary in most cases to make sure that you've got the right people and that the team is overall inspired and working well together.

Michael Koenig: It's so true that it entirely comes down to people. And so that was a really nice segue into the next question I have. If you look at Automatic or Shippo at the times you're entering these businesses, you're in the hypergrowth stages. And during hypergrowth, sometimes the skill set of the people who got the company to that point aren't necessarily the right skill set to go beyond. How do you manage that? How do you evaluate it? And then how do you make the necessary changes while not rocking the boat too much, leading to more turnover?

Catherine Stewart: Yeah, oh my goodness, people management is really the name of the game. Um, it's funny, I've only run HR for one year of my time, but HR questions are so important because ultimately the tools that you have to work with are, are the quality and the kind of the people that you have, and having the people be matched to the right, um, jobs and roles, and then providing those people with what resources they need, whether that's mentorship, or whether that's more headcount, or whether that's a better work environment in some other way, or better processes. So I think it really does come down to people, as you described. And I think that there are all kinds of challenges that companies experience when they go through hypergrowth. So for example, at Facebook, The company was about 2,500 employees when I joined, and that was about a year and a bit before the, the IPO, roughly. And the company was growing so fast, it was doubling headcount at least year over year most years I was there. And sometimes we did that better than others. Doubling headcount while keeping the quality of the talent high is quite challenging. And I remember that the first year I joined, I guess the first year, the year after I joined, there was one year where we relaxed our quality standards a little bit too much. And there was a bit of a meme, almost like a vintage of wine. It was like, don't work with engineers who were hired in 2013 because, you know, that was the year when we opened the floodgates a little bit and we just cut corners and just needed people. And that really slows you down later, whether because suddenly you're now trying to fire people who aren't a great fit or because products are not being built in the way that you want. And often people who are not the perfect fit will be hiring, right? The first thing they need to do in hypergrowth is to start hiring. And so if you have somebody who's not a great fit and then they're hiring more people like themselves, that can also sort of exacerbate the issue. So it's a real tension. How to hire quickly. But well. And that's where I think the, some of the attrition numbers and some of the processes can really, can really be helpful in terms of measuring how well you're doing that. Another challenge that companies will run into is how to layer, because often you do have the right people, but it's very easy to give out titles when you're young, and maybe what it means to be a VP at a Series A startup is different than what it means to be a VP of the Series D company. And how do you bring in the right amount of outside talent while still developing the internal people and making sure that they have lots of opportunities to continue to rise and grow and stay at the company? And it's a real balance. And I think that's where the art comes in because it's rarely the right answer to just hire externally exclusively and to layer everybody. Who's at the company to start with. On the, on the flip side, you do want to make sure that you're bringing in external people who have the skills and experience to buttress the existing team and to improve it and to bring it to that next level. And I don't think there is a one-size-fits-all answer. It really comes down to getting to know the team that's in place and where they're strong and what they need and what their career aspirations are. And then working within that to make sure that the star players have what they need and the support they need and the opportunities they need to stay, but also bringing in the external talent where there are holes and gaps in the company to make sure that the company is living up to whatever the new expectations are, right? You go out, you raise a Series C or a D or an E, and suddenly, you know, the new expectations are even higher than whatever you were hoping to achieve before., and you need to make sure that you're ready to execute against it.

Michael Koenig: Much easier to give a title than take it away. So there's a lot of management that comes, that comes with it. And you said there's no one size fits all. I'm glad that you said that. Otherwise my next question would've been, what's your secret? So in terms of your switch to becoming COO, from Chief Business Officer. What surprised you about the role?

Catherine Stewart: The role of COO at Shippo after CBO at Automatic? What surprised me about the role? I think what it means to be a COO at a company, or really any of these C-level titles often, is quite different depending on what the company needs. And somebody once told me, you know, in tech, COO is whatever job the CEO doesn't want to do. If the CEO is the founder, that's often the case. So if you have a technical CEO, then the COO job might be everything that isn't technical. But I know COOs who are also running product and engineering. And at a lot of companies such as healthcare startups or health tech startups, sometimes you'll see the COO is just running HR, finance, legal, and any other sort of back office, more supportive roles, as opposed to go-to-market, front office, revenue-generating teams. And the CBO in a lot of those companies will do the go-to-market side. And all of these roles— and some companies, CBO really just means pricing or special projects or strategic planning. And so it can be It can be almost anything you want it to be. And the you in this case is often the CEO. And getting to know what it is your CEO wants and expects is, I think, the first step. And ideally that happens before you even join the company. So you say, hey, what is it that you like to do with your time? Where is it that you feel like you shine? Why are you looking for this role? Like, what is it that you want to spend less time on or that you want to go better than it's going today? And then let's see if that's a fit because here's what I'm strong at. And if there's too much overlap between us, then actually it may not be the best fit unless what you really want to do is gently retire. Or if there's, if there's too, you know, too little, then how do we make sure that we, we also bridge those gaps and we're speaking the same language and we're working alongside each other as a team and are really well aligned in terms of our priorities. So I'd say those are the conversations to have even before joining the company. Because ideally there shouldn't be too many surprises once you do. It's better for everyone if there aren't.

Michael Koenig: When joining a new company, do you ever feel the urge to maybe recycle some of the policies or some of the procedures that you had at prior companies?

Catherine Stewart: Yeah, I mean, when things work, That's what, that's what learning is all about. It's saying, hey, when I saw this problem at XY

Michael Koenig: I was just gonna comment on that. Certainly in going from Facebook, 2 Automatic, 2 very different company cultures. There has to have been some sort of adaptation, if nothing else, just within your mindset, I'd imagine.

Catherine Stewart: They are, they're very different companies. I think that's the beauty of experience though. Um, it helps me, uh, honestly, one of the experiences that very few people think about in my in my life, when they looked at— when they look at my LinkedIn profile, the experience most people tend to just kind of raise an eyebrow at and then just quietly move on from is, is my time at Random House. And yet that was a really important time in my career because it gave me a chance to see what it is like to work at a very successful, the world's largest English language publisher. But a very old-school company, and to get a feel for what are the pros and cons of managing this way. And then to go to Facebook, totally different. Yeah, really different. What are the pros and cons of managing that way? And that way you can start to cherry-pick some of the things that make each of those companies great in very different ways. And to try to move fast like Facebook, but then also to have really high-quality managers and an emphasis on people and developing people and keeping people at your company for 20, 30 years if you can, and having deep industry experience. Like, there are certain things that Random House does really well. And how do you take all of these, all of the gems from, from the different companies that are out there and the different ways that you can operate a company and, and try to put those together to, to make your company great, as opposed to your company a bit of a stereotype or just doing it the way every other company in the industry, industry does it, because there are always pros and cons of different approaches. And it's, I think, helpful to be thoughtful about which are the pros and which are the cons that you're willing to, that you want to have within your company, if that makes sense.

Michael Koenig: So in terms of getting advice, it's very difficult to find advice for COOs. It's so situational. But we all have a few mentors that we go to every now and then when we have a new challenge or need some advice, need to, to have a sounding board. Is there any that you could share that you experienced that you've carried forward?

Catherine Stewart: Maybe I'll go back to Random House. The beauty of working at Random House was working with people who had been doing something well often for decades. And the kind of person that I got to work with there is very different from the kind of person I ended up working alongside at Facebook, who were often really smart, very hungry, very, very competent, but often had only been working for maybe 8 years or 6 years or 10 years. And so some of the things I think back on, I learned from, from people at Random House, especially around management. And how to build things that will last and how to develop talent. And I remember I was working for somebody who later became the COO. He's the COO at Penguin Random House now. He was more junior in his career then, but he— I was very eager to get a promotion at the time. I've been doing well, and then there had been a promotion freeze because it wasn't the best of times in publishing back then. And he told me, hey, don't be, don't be too eager. Don't, don't measure your success based on your title or your compensation. Like, those are, those are helpful things to keep track of, but ultimately it's what you learn and it's what you know, because you won't be in this job forever. And when you get to that next level, what determines whether you succeed in that level or fail, or it will often be what you've learned. So don't be too eager to move ahead. Move ahead when you're ready. Move ahead when you already know how to do that job well. That was something that stuck with me. I think depending on the moments in time, different pieces of advice or wisdom, um, stick out to me. But I do feel that I've learned different pieces from different companies. —like I remember at Facebook, one of the things that was frustrating at Random House was we moved very slowly. We would launch products so much more slowly than it felt like we could and should. And the movement from physical to digital books was something that took the company years. I'm not even sure they've still finished in terms of just changing the workflows and optimizing for the fact that everything can be digital first and really should be at this stage. And when I was at Facebook, we launched the Audience Network, the Facebook Audience Network, in about 3 weeks. The way we did that was just by getting a tiger team together, and the company was sufficiently disorganized that we didn't even really get any sort of higher-ups approval. We just said, hey, wouldn't this make sense? Let's just build it, and we'll just quietly launch it because things are disorganized enough that, you know, probably we won't get caught. And if it's doing well, then it's gonna be really hard to shut down because then it's doing well, you know. And that's exactly what happened. There wasn't some sort of special approval process to get that product going. We just needed enough people to buy into it that we could actually just build the thing. And it was so chaotic and cowboy and Wild West that we did. There was really no bureaucracy to stop it. And that was a pretty spectacular experience to have, to learn how you can do something with fewer people than you expect you need. With less process than you might think you need. And then you just iterate. And that was the Facebook way, right? Just launch it and then we'll make it better over time. And there, again, there are pros and cons of different ways of managing a business. And I think it's helpful to pull whichever process suits that company best. If you're doing zero to one, I think launching fast and iterating and learning and relaunching if you need to, just hacking it together makes a lot of sense. But if you're talking about a product that's already serving lots of customers and you're really at a point where you need to scale, then I think you often want to plan a bit more for the future and be thoughtful about where this company is going and where this product's going, and just try to build it the one time in a way that's scalable so that you're not— so that you are actually moving quickly in the longer term, so that you're not redoing it every 3 months or so. Um, so again, I think that it's like having a toolkit. Lots of companies have different ways of doing things. And I think that the best way is often very dependent on the situation and you just want to try to read what the company needs at that point in time.

Michael Koenig: That's part of the beauty of software, isn't it? That you can move so quickly, but eventually as the company grows, I mean, you certainly couldn't do that at Facebook now. Right. And I wonder. What you just described is this really entrepreneurial mindset that Facebook has embraced, that, that most tech companies embrace in general. I wonder how you maintain that entrepreneurial value as a cultural value, that is, as the company grows and you have to come in as a COO and start having more process, start introducing some best practices. How do you do that and still balance the entrepreneurial mindset?

Catherine Stewart: Not everyone has to be an entrepreneur. Your risk operations team, your legal team, they don't necessarily need to have the entrepreneurial mindset. They need to be able to work within it. Um, they need to be able to support that kind of development and not slow things down too much. But you probably don't want a lawyer who's hacking together contracts and just getting it out the door at 80% good enough. So I think it depends on, I know I keep answering, but you're asking me a lot of questions about people management, and those are just hardly ever black and white in my mind. And what I like to do is companies scale and grow. So Automatic at the time I left was almost 1,300 employees. You don't want everyone to be entrepreneurial. Things will not work. If that's the way everyone's trying to get things done. So you need, you need teams to be coordinated. You need teams to know what other teams are doing so that they can, by the time the product launches, there's a product marketing plan that goes out at around the same time. If not, you know, you don't want surprises when you're operating at scale. So what I like to do is have tiger teams, as I call them, pockets that are small, and don't have a lot of bureaucracy and have the freedom to innovate and to iterate and to try new things. And they need to have whatever resources, with some exceptions. They probably don't need their own finance person, but they probably need their own engineers, their own product manager, their own, you know, business person or 3 business people, whatever, whatever the needs of the product or the initiative are, so that they can just go run. Quickly as possible. And they don't have, they have the oversight they need, but they don't have too much. They own too much process. And that's how I like to preserve innovation within a larger company. I like to separate it out in some ways.

Michael Koenig: Well, it's interesting because you're talking about some of the GNA and what you described is sort of setting up guardrails or bumpers where people can just kind of, hey, fly throughout this process and build build and experiment. And I've set up processes though. We have our legal team that's going to make sure that no one's breaking the law. We've got our finance team to make sure that this isn't going to bankrupt the company. So it seems like it's setting up the guardrails but also creating the space for the creative magic to, to continue on. Yes.

Catherine Stewart: And I think it's so important to not overly venerate a particular company as well. Like, this is the way to do things. I'm hearing like back in the day it was Google, we need to all copy Google, we need to all copy Facebook. And now it feels like we need to all copy Stripe, we need to all copy Twilio. And I think things go in vogue and out of vogue, but there are pros and cons. Like the Facebook move fast and break things is quite effective for moving fast, especially if you're an engineer. But the Cambridge Analytica issue and some of these fake news issues are byproducts of moving quickly without having everything figured out. And depending on what industry you're in, you can get away with that more or less. So if you're Coinbase, you may not want to move quite as fast and quite as, you know, breaking quite as many things because you're operating in a world that has a lot of compliance issues. Like Robinhood, it's another great example. Like, you— when you're, when you're guarding people's money and you're working with large institutions, it's a different standard. And so I think that copying Facebook is great for the right situation, and copying Stripe is great for the right situation, but don't include more overhead than you need. Or less than you need. That's the art and the magic of being an effective operator and leader, is how much process— what's the minimum process I can get away with that will keep this company from wasting a ton of time by making a costly mistake?

Michael Koenig: Well, that kind of ties into the last question that I have, which is for the COOs that are going into a new company, new role, meeting a new team, what advice can you give them?

Catherine Stewart: Often when you join a new company, particularly if it's a different industry, you will need to become expert quickly, very, very quickly. You also need to become an expert quickly on the culture and the individual people and their strengths and weaknesses. The new company. You will need to become an expert on your partners and your customers and their needs, and also the technology that, that company is providing, and the competitors. There's so much to learn. I would say succeeding when you are stepping into a new role often has to do with how quickly you can learn, because if you're still learning what makes the competition better or weaker than you are, you've been at the company for 9 months, it's too late. It's way too late. So how can you accelerate your learning so that you get it done? And you're always learning, of course, but you get the most important things done, um, either before you join or within a month or two. Because also know that people will expect you to start having quick wins. And operating. I think I started— I, I was within 3 days of joining Shippo, I was on a call with USPS negotiating a contract. Um, so you will not be able to stop and take a break. Once you join, you're in it. How do you balance the learning and the executing? And how do you learn whatever it is that you need to know to be effective as quickly as possible? And part of that is even figuring out what company is a good fit for me. Where, where do I still learn But maybe I have enough knowledge to know that if it's— if I'm used to operating in a B2C environment and this is a B2B company, and also it's in a different industry, and also I haven't worked with a lot of these employees before, like sometimes, you know, people follow each other in cohorts and sometimes they don't. So don't try to— don't try to set yourself up for an impossible feat. Make sure that, you know, you're learning enough to keep yourself fresh, but it's something that you think you can achieve. Whatever the company needs, that's something you think you can give it within a pretty short period of time.

Michael Koenig: Well, Kathryn, thanks so much for coming on the podcast. Where can people go to keep up with you?

Catherine Stewart: Oh, I don't know. Definitely not Twitter. Don't go on Twitter to keep up with Kathryn. I'm pretty active on Instagram. I guess I'm still loyal to my old employer. LinkedIn is fine. Probably LinkedIn is best. LinkedIn. LinkedIn. Or I have a website, of course, built on WordPress.

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