Katie Harper - Managing Isolation as a COO
A while back I realized that while I’d been a COO, I hadn’t interviewed many for the series. When COOs do their job well, we don’t notice them so I wanted to bring more of them onto the series to reveal their work. I’m so grateful that I found Katie Harper, COO of Kard through our mutual connection Edwina Johnson.
We talked about isolation, a topic that’s so important for all leaders but especially for COOs who are often responsible for large parts of the organization and hold a great deal of confidential information.
We talked about
How leadership was different than she expected
How she knows if she’s doing well in the role
Her process for finding mentors
What she did to feel less lonely
Ok, let's get to introductions. Can you introduce yourself?
I'm Katie Harper. I'm currently the COO at Kard, a rewards-as-a-service platform. We focus on card-linked offers, working with any company that issues a debit or credit card and partnering with merchants that want to run ads in those issuer environments.
About me. I grew up in a small town in North Carolina in a military family. I was homeschooled for part of middle and high school and then went to a “middle college” program for my junior and senior years. I graduated with enough college credits for a two-year degree, but I opted to go to Duke, which didn't take any of the credits. (laughs) I got four full years of college and studied computer science and Russian. I didn't know what I wanted to do when I graduated, so I went to graduate school in computer science and ended up hating it. So I dropped out. I was pretty embarrassed by that. It was my first real failure. I moved out to California at the time and started at a company that I didn't know was failing. I accepted the offer sight unseen. I ended up staying for nine months. It was always a gamble if we were going to get paychecks or not.
The positive was that I got a lot of experience because there was so much turnover at the company, and I got to take on a lot of responsibility. Then I found a job on Craig’s List for a startup. I didn’t know what a startup meant but I joined as employee number eight and worked with that company through their Series B, when there were about 80 people. I knew I wanted to move to New York and be early-stage again. I lucked into Kard and have been there ever since.
What a great journey. That must have been so perilous to move across the country for a job at a company that’s failing but that’s what it’s like at startups. There’s always a concern: Do we have runway? Is the market going to hold up? Do we have product market fit?
There's a lot that has to go right. It didn’t feel particularly risky at the time because I had so little in my life that depended upon me. I was 23. I could have moved home if it really got dire, but I happened to find another job, thankfully.
It underscores, you know, the role of C-suite folks in startups. It's so much pressure. There are so many variables and complexity coming at you.
Yes, I think it's something that I try not to reflect on too deeply because it can be overwhelming, but it is knowing that 60 people’s jobs depend on how I'm performing in my role. That's a big responsibility.
I dropped out of grad school too. I was going to get a PhD in sociology. I dropped out of that program and just got a master's degree. It felt like a failure.
Yes, those are a big deal. I think it's trendier now to say, oh, I was a dropout of X, but it was not something that felt good at the moment at all.
I think part of that was what drove me to so quickly want to have an impact on a company. The sense of failure and the inability to contribute drove me to want to join a small company to have an outsized impact.
How did you get into leadership? Did it just sort of come as you were trying to have an impact?
I think it started earlier. There were 26 people in my high school’s graduating class, and I was the class president. I was in the marching band at Duke and was the president of that for two years. It's one of my nerdier things, but looking back, it gave me a great opportunity leading 100 of my peers in an unstructured volunteer role, where there was a significant amount of responsibility. I often worked 35 - 40 hour weeks doing that in addition to all my schoolwork.
When I joined the first startup, they made me the manager of the team I worked with after a year and a half. I was 25 at the time, so I got an early chance to manage employees. That was an opportunity that I probably would not have been able to get if I'd been hired somewhere else. So I've gotten very lucky in the chances that have come throughout my career.
Being the class president and then president of the marching band, what led you to seek those roles?
For the marching band, it was that I didn’t see someone else ready to step into the role. It wasn’t that I wanted to be in charge, it was very much, “I’m not sure who else will be” and I felt a deep sense of obligation to make sure this went well.
You’re articulating something I think is misunderstood about leadership – that people want power or to be in charge. Some do, but there are plenty of people who feel this deep sense of responsibility and that's why they get into leadership. They see a void and step up into it because they want it to go well. It’s how I’ve gotten into leadership too.
Yes, and sometimes there's a misunderstanding of, “Oh, you love to lead a company, so you must always lead.” Actually, I really love to follow.
Was the C-suite something that you had envisioned for yourself?
When I was in my mid-20s, I was looking to set goals for myself. I found it much harder to set goals at that particular time in my career, so I decided that C-suite was a goal that I wanted. I had it in my mind that I’d be in the C-suite by 30, which is such a silly and particularly aggressive role goal… and I did it. But I put parameters on it. It wasn’t ‘C-suite at all costs’ because I could start my own company and decide to be CEO. I wanted it to be a C-suite role at a meaningful company by 30.
I distinctly remember the conversation with the CEO telling me he was planning to promote me. I got tears in my eyes. I think that there's an expectation that it's going to feel a particular way and then, “Oh, that's all it was.” None of my responsibilities were changing. I was so grateful and yet it was almost a letdown of how I planned I was going to feel at that particular moment. Sometimes putting too much emphasis on that sort of outward recognition is faulty. I think I've had to learn that the hard way a few times.
My first boss said something to me about wanting to be a 10 out of 10. I think that was part of my difficulty in grad school, I was never going to be a 10 out of 10 computer scientist in my mind. I never cared enough and never had quite enough natural aptitude. Operations was something I always felt that I could be a 10 in. I loved that it was so broad. There are so many ways to define it. I thought, “maybe I could be a 10 at that.” And if I'm going to choose to be a 10 at that, I want to be the very highest possible best that there can be. Maybe that was part of the reason for the C-level goal.
Doing well or achieving a target seems to be a motivator for you.
I would say yes, often to my downfall. A lot of my life was very achievement-oriented. I think the disappointment I felt in achieving the career goal that I’d set for myself was that I didn’t feel any different. That's sort of a theme I've had to process in other parts of my life too. I try to channel my drive into hobbies sometimes just to give myself something else to focus on and not be quite so achievement-oriented.
There’s no bar that tells me if I’m doing well or not. If the company’s doing well, maybe I’m doing well, but there are so many other factors that go into that. I’m constantly trying to assess where I’m needed in the company and whether I’m doing that particular role well.
Thank you for sharing that. How did the role at Kard come about?
I started as the Director of Operations at Kard. Six months into the role, it was looking like the company was going to fail, so we trimmed the team significantly. I had an offer for another role but decided to stick it out for six more months, because it would be so personally satisfying if we could turn Kard around, so I chose to stay, taking on a lot more responsibility and significantly helping with the pivot. When we completed it, that helped move me to the VP level. We continued to execute pretty well. We happened to luck into a lot of the right things at the right time. I’d felt that the CEO treated me more like a peer, like we were fighting together. I think that's what helped lead the conversations to being promoted to that particular level. I think it's also incredibly difficult as a solo founder. You're a party of one taking on the whole responsibility of the organization; that's a tremendous role to play. We are currently the only two C-levels at the company, and we've been working together for a long time. We have complementary skill sets. The joke I always make is that our Venn diagrams don't overlap at all. That’s been helpful in understanding what I'm good at, what I need to cover and what I know that he can cover, and what I trust him to do.
So there are only two in the C-suite. How big is the company?
We have about 60 full-time employees right now.
What are you responsible for as COO?
Of the VP level, the three that report to me are the VP of Engineering, Product, and Finance, and then under Finance is HR. I also run marketing right now. Each of the leaders within their particular verticals is amazing at what they do. I think about how the company is running overall and how the pieces are coordinating together.
The two go-to-market teams both report to the CEO, but I still keep tabs because there's so much operational stuff that happens there too. I'm not wanting to overstate my responsibility, but a lot of it is the internal workings of the company. Ben [Mackinnon, CEO] is so great at the external-facing stuff and speaking with investors and fundraising, getting on stage — all the things that I'm not good at. So I try to focus my time on everything else within the company.
That sounds about right for that size of company. How was the role different from what you expected?
I think it's hard to know what to expect in operations just because it can be so varied at different companies. It also depends on the strengths of the leadership team that you're working with – understanding where they're particularly great and where I can fill in the gaps because operational work is usually a lot of filling in gaps. I don't know that there was a moment when I had moved from the VP level to the C level and thought, “Wow, this is so different.” The mentality at Kard is that you sort of step into the role and take on all the responsibilities and the title comes later. So it was the stuff that I had already been doing that felt expected.
I have mostly been mentored by CEO types, which has been helpful for me in understanding my own role with my current CEO — understanding what he likely should be focused on, what he should be expecting from me, and how I can fill that gap. Hearing it through the lens of past or current CEOs from different companies was particularly helpful. So that CEO group was a mix of people that I worked with or specifically sought out. I try to keep that group fairly small, just because it's such a deep and personal relationship when you're sharing everything that's happening with you in your current role and where you want to go in your career. So I keep five people in that.
What's been most difficult about being a COO?
There’s no bar that tells me if I’m doing well or not. If the company’s doing well, maybe I’m doing well, but there are so many other factors that go into that. I’m constantly trying to assess where I’m needed in the company and whether I’m doing that particular role well.
I think another piece that's similar across probably all leadership roles, but it can be very isolating. We are an all-remote company right now, which adds in some ways to isolation, but I think isolation also stems from the amount of knowledge that I keep, with some of it confidential. I'm looking at the whole inner workings of the company. I'm being a thought partner to the CEO. There's a lot that I have to keep inside and a lot that falls on me specifically that I can’t easily share.
Have you felt this isolation in other roles or has it come about as COO?
I think any leadership role is a little bit isolating. I remember feeling it when I was leading the band, because there was stuff that I would know or be privy to or decisions that I would have to make that would affect my peers. That felt isolating.
I think even now, knowing who we're moving forward with, who we're choosing not to keep on the team, all those sorts of decisions are very brutal for me. I can't vent to someone at the company because most of the company reports to me in some way. I have to be very thoughtful about what I choose to share or not share.
I think that as a leader, you're always wanting to be a good listener. I think listening often requires vulnerability. It can be hard to be fully vulnerable when there's something that you know that you can't share. You also don’t want to be duplicitous either. Those are things that I have to weigh a lot in terms of how I communicate with those around me.
I agree that almost every leader feels this way. COOs and CEOs might feel it a bit more given their roles. How did you handle the isolation?
There are a few outlets that I've found that have worked. When I’d switched over to Kard, my old boss had told me, “No one is ever going to feel sorry for you. Everyone will always be vying for your role. So you're going to have to find a group of peers that you can be open with, because you can't vent to someone at the company.”
There are also two different types. Sometimes I just need to vent and have someone blindly agree with me and say, “Yes, you did the right thing.” Sometimes I need to vent in a problem-solving way. I use mentors for that particular thing. Sometimes I need to be understood. I’ve found that peers in similar roles can be the most helpful with that. Being able to say, we're in this particular stage, we're struggling with fundraising, we're struggling with setting OKRs, and have someone go, yes, here's how we did it. To have someone quickly pick up what you’re trying to say and know what it feels like. Having someone understand what I’m talking about, and say “This is valid, this is normal, and here’s something you could try” has been really helpful for me.
What's their career path? Not just promotions, because that's only one aspect, but can they grow in the role I’m offering? Is there an area with capacity for them to evolve? We need to think about growth with leaders. Great leaders always continue to grow in a role and want to stretch themselves.
How hard was it to figure out that support system?
It's been a lot of iterations over time. There was a turning point when I was in New York where I just wanted to meet people who were in similar roles to me. I wanted to see what they were doing so I could assess, am I in the right peer group? Am I doing the right things in my role? Just to have people to call on. So I partnered with someone else, and we started monthly beers and called it “Hoperations” — a group of people we could get together and vent about all this stuff and see what they were reading or thinking about. That was really helpful. We still have periodic text message threads where someone can reach out and say, “I’m dealing with this thing or someone reached out to me for this role, is this something you’re interested in?” A peer group was something I needed.
Peer groups are really powerful. What about mentors? How did you figure out your mentors? Were they people you’d worked with in the past or did you seek them out?
It's been a mix of both. I have never been formally mentored by a previous COO. I realized that was probably a pretty significant weakness of mine.
I have mostly been mentored by CEO types, which has been helpful for me in understanding my own role with my current CEO — understanding what he likely should be focused on, what he should be expecting from me, and how I can fill that gap. Hearing it through the lens of past or current CEOs from different companies was particularly helpful. So that CEO group was a mix of people that I worked with or specifically sought out. I try to keep that group fairly small, just because it's such a deep and personal relationship when you're sharing everything that's happening with you in your current role and where you want to go in your career. So I keep five people in that.
How did you identify and connect with them?
Two of the five are the previous CEO and CTO from my former company. I had great relationships with them, and they've always been on my side. One was a CEO who chose not to hire me. He said, “I'm not gonna choose you for this role, but I would love to stay in touch.” So we got monthly coffee and did that for four years when I was in San Francisco. We were just emailing yesterday. It's a relationship that I fostered over time, not knowing that it was going to be a mentorship or anything else. I had really wanted to work with him. That didn't work out and I pursued another path. Another was someone that an investor had introduced to Kard to see if there was maybe a fit for a particular role or aspect of advisory. I reached out to him later to say, “Hey, I loved our conversation so much. Would you ever consider mentoring me?” So I've been working with him for the past couple of years. And then one was someone that I happened to luck into meeting at a wedding and he was in a similar sector. We’ve talked a lot about particular aspects of my career that have been helpful for me.
That's great. Thank you for that breakdown. My favorite might be the CEO who didn't hire you. I think there's this feeling like I didn't get the role, there's something wrong with me, they didn't like me, but that's not always true.
He came back and told me the reason maybe a year and a half later, and it was that he thought I was going to be too good at the role, and that I was going to drive him crazy with how much I would want to do, and he didn't want to deal with that.
(laughs) How did that make you feel?
How flattering. That was such a nice thing to say. It was funny that it took him so long to say it, but I don't know that I was ready to hear it before that moment. It would have felt shallow maybe to have someone say you would have been too good for the role. It's just an easy way to reject someone and not have it feel hurtful, but it was deeply flattering.
I love that he confessed that later. But it's true. Sometimes somebody is going to outgrow the rule, or they're going to push us in ways that we're not ready to be pushed as a human or as a business. And that's really OK. That's just the nature of business.
I think that's part of hiring sometimes that people forget. It's not just fit in the role now, it's fit in the role long-term and where they want to go. Can I give them the things that they desire in their career? I never want to hire someone where I think like, yeah, I'm just going to stuff them into this role and hope they last for six months. No, I want to be thinking about whether I can help them grow as people and in their career overall. And sometimes you turn someone down because what you have to offer is not fair to them.
What's their career path? Not just promotions, because that's only one aspect, but can they grow in the role I’m offering? Is there an area with capacity for them to evolve? We need to think about growth with leaders. Great leaders always continue to grow in a role and want to stretch themselves.
That's a good way to put it. That's something I've had to be more thoughtful about leading VPs. It’s flattering to have any VP who wants to report to me because I feel so junior in my career sometimes. I have to be thoughtful about what I’m offering them. I'm likely not offering them any expertise in their particular sector because they're so much better at it than I ever would have been. I'm trying to offer them a view into the company that they may not otherwise see, or people from my network, or a shot at something that they may not have gotten at another company that we can offer. I try to be more just aware of those things in terms of how I'm helping someone grow their career as their manager.
Finding someone who you can be entirely open with is very helpful, whether that's a peer group, a mentor, or even a partner sometimes. It's really helpful.
Yeah, COOs are often leading people where they aren’t experts in their functional area. I interviewed Edwina (Johnson) about this. It can make us wonder what we have to offer them. However, COOs know how to collaborate across company lines. We have to work with everyone, otherwise you can’t get the job done.
That's a good way to put it. That’s something I've tried to play up as a particular strength, just the knowledge that I can bring from different parts of the company that maybe are not as visible to everyone else.
COOs are good at thinking about the business and the organizational layer. That’s a great lens for leaders, even VPs to get more sophisticated about that organizational layer.
Yes. One misconception I've sometimes seen is that, oh, you're the COO and so everything with an operations title must report to you. There are no people with operations titles reporting to me at all. I don't know if that's right or wrong, it's just the way it's happened, but my role is more about how the entire company is operating. Again, my performance should be based on if the company is doing well or not. If it's not doing well, I do think that a significant part of that is on me.
Right, it’s about what the company needs and how it needs to organize itself including reporting structures.
Yes, and we've changed it significantly over time. For instance, engineering and product only started reporting to me in the past year. There have been significant shifts as the company has grown in terms of different departments or different parts of the organization that have popped up. We've changed a decent amount.
How are you feeling about isolation today?
I don't think it's ever something that goes away. So I can only think about compensating factors. I would say that a significant change I made in my life a couple of years ago was that I moved from New York City down to Florida. I had bought a place in New York and my brother was living in the city when I first moved out there. He ended up leaving during COVID, and Kard went entirely remote as a company. It was just so hard for me to work out of my apartment every day alone and not have the office that we used to go into. So I thought, how could I make my daily life easier because my job life is so difficult? There was a house in the family that was sitting empty in Florida, and I just would periodically spend a couple weeks down here. It was nice to have a slower level of life that I enjoyed, so I moved full-time. I spend my weekends at the beach or diving; I'm trying to do something very low-key in compensation for how difficult my work life can sometimes be. And I think that's been a huge help for me.
What a personal life looks like can really matter in terms of combating feelings of isolation.
Yes. I'm still working out of my home alone all the time, which can be isolating, so I continue to think through what my support community looks like here. Part of the piece that's been nice is that my work life is so separate from my normal life. There are very few people here who know most of what I do or the stakes of the company. It's nice to sort of turn off my work brain and engage with my community otherwise here.
What advice would you have for other leaders who are battling isolation?
Finding someone who you can be entirely open with is very helpful, whether that's a peer group, a mentor, or even a partner sometimes. It's really helpful.
Sometimes I will call my mom just to get to vent about whatever has happened that particular day. It's nice to call my CEO and to vent about things sometimes and to just have him go, ”I know, me too.” So finding someone who will have that voice and that understanding in any capacity. I don't think that there's a set rule for what that looks like.