Finding Balance With the Weight of Being a Product Leader

Lauren Nagel, VP of Product, Stackhawk

I met Lauren Nagel, VP of Product at Stackhawk at their offsite where I facilitated a session for their leadership team. I was lucky to sit next to her at dinner where I got to learn more about her. I’d been wanting to feature more product leaders on the series and was happy she said yes. Our conversation covered her leadership journey, why she took the role at Stackhawk and her advice to other product leaders feeling the weight of responsibility.

It's so good to see you. I last saw you in October at an off-site for StackHawk in Colorado.

Yes. It was lots of fun. Very effective.

It was fun. It's such a great team. I'm excited to talk to you today. For everybody else who doesn't know you, who didn't get to spend a day with you, can you just give us a little bit of an introduction of yourself?

Sure. My name's Lauren Nagel. I am currently VP of Product at StackHawk, which is an application security testing software company. I've been in software since I was 10, I think. Something crazy like that. Started as an engineer, after college, at Microsoft. Then, I very naively and arrogantly decided that I could do better, just not designing any bugs in, as opposed to finding them later on in the product. Became a product manager. Moved to my first start-up from Microsoft, which was a blast and got me hooked on start-ups. That was acquired by Cisco. After that, I kind of bounced around a little bit. Stayed in consumer home networking for a while until I fell into dev tools about seven years ago with web performance. I was at a start-up called SOASTA which was acquired by Akamai.

I was at Akamai for about three years. Led the digital performance management and the web performance pieces, there, for a while. Then, in my last year, I shifted to helping them shift to a cloud-first strategy so we could keep up with Cloudflare and Fastly, and all of those cloud-first solutions that had come along after Akamai had already been created. Then, I had a former boss from SOASTA and Akamai, who had gone to New Relic, who recruited me to New Relic to lead up their front-end web performance. I ended up leading a good portion of the observability portfolio at New Relic for a while and then was recruited into StackHawk, which has been a wonderful decision. I was brand new to security. Because we build developer security tools, they were actually very excited to have somebody who knew developers and not security. So, it was a good fit, and I got to come back to my love of all things start-up, all the good, the bad, and the ugly of start-up life.

During all of that, I have a great husband. We've been married for six years. We have a three-year-old daughter. I have two big dogs who might very well bark during this. If they do, I apologize. I will mute it as quickly as possible.

We'll get to meet the dogs through some barks. (laughs)

Probably. Let's see. Born and mostly raised in California. Yeah. That's me in a nutshell. So about, I keep saying 15 years, it's probably more than that. 15 years and change in software, officially. 

That's a great introduction to yourself. For context for everyone, how big is the StackHawk team?

We are about 45 ish people so just under that 50 mark. I think I was employee 30 or so, and I just had my one-year anniversary yesterday.

Hey, happy anniversary.

Thank you. Yeah. So, we've grown quite a bit since I joined, over the last year.

Yep. How large is your team?

Currently, I have one PM and one I just hired, who will start in January. So, we are a pretty small product management team. Design also reports to me, with our VP of design and his team, which is two designers and a content writer. The PMM also currently reports to me, which is a team of three people.

Okay. Perfect. Got it. All in, around 10 ish?

Yeah. 10 ish with four directs.

Yeah. So, not quite a quarter of the company.

I have not thought of it that way. I probably shouldn't. It would freak me out.

Oops, sorry. You and I got to have a really lovely dinner when I was in Colorado, and we spent a lot of time talking. One of the things that stuck out is the weight of responsibility, the weight of leadership. I'm just wondering if you can sort of talk about when you first felt that weight.

Yeah. I was one of those kids that always felt like, "I need to be good for my parents," so that they didn't worry, so that they felt like they were good parents. Right? I was always that kid, the one who wanted to make teachers feel like they were successful teachers. I don't know why I took that on. I've done much self-development and personal growth work to not take on everybody else's feelings and emotions anymore. I do think I kind of naturally felt that weight.

From a career perspective, I very clearly remember, I was at my first start-up and we had been acquired. That acquisition wasn't awesome for me. The start-up had been just such a special time for me. Then, everything changed, and the new company and I just didn't mesh.

I remember, my boss at the time. We'd all stayed together as a team from the start-up, and he was so supportive of me. We'd known each other from Microsoft, and he took me out to coffee. I'd been really upset and kind of sharing my malaise with everyone. He was like, "You can't do this." He's like, "You are a leader at this company." I was still an individual contributor. I thought, "Well, I don't have a title. I'm not a VP. I don't have anybody that reports to me." He said to me, "You are a leader. When you are out there sharing your upsetness with everyone, it brings people down." He gave me a talk. He was like, "Look, either you can shift, or you should leave." Right? He wasn't at that moment firing me, but that was a very clear conversation.

I still think about that moment. I think that was the first time I realized you don't have to have a title to be a leader. Some, I think, are genuinely born leaders. I think some people grow into it. When you are in that position, however you get to that place, you need to recognize it. You have to own the impact that you have on those around you, being in that position. Me, throwing a tantrum about being unhappy with everybody else at work, was having a huge impact. 

I'm physically kind of small, but I'm not a small presence. I'm loud and I make myself known for better or worse, depending on the situation. Right? I don't say that out of ego, but out of acknowledging and owning the presence and the impact that I know I can have. So, that was a really clear moment for me.

I still look back on that, and I still take things from that moment as I grow as a manager, a leader, and an organizational leader. I will always have respect for the manager that had that conversation with me. Now, I've had to have those similar types of conversations. That also adds to that weight because you think, "Gosh, if someone else has to give me that feedback, that's really hard to do." Right? It's hard to get [that feedback]. 

You have to care enough about that person to give the feedback, as well. So, to understand how much that manager cared about me, and then realize, "When I give that feedback to other people, that's a way of showing love." That is a way of being a leader, of helping someone, redirect them, give them a different perspective, be like, "Hey, you're not on a path you think you're on, or that you want to be on. I know this, and I love/respect you, and let's see if we can reposition you."

It sounds like it was such an impactful conversation. After that conversation, did you change your attitude, did you leave? What did you do?

I did both. I changed my attitude, and I realized I needed to leave. I changed my attitude and in doing that, moving out of just being a complaining victim in this situation, I realized I had taken action. I tried to take a little more action. Then, I realized the situation wasn't going to improve for it to be healthy for me to stay. So, I did leave.

What a great opportunity for you to learn about impact, and "Where do I want to be?" To recognize that you have an impact, so young, I'm sure carried you into leadership in a different way.

Yeah. I definitely think so. It did help me.

I don't know how many people out there are product managers, but it's not one of those paths that... Promotion does not happen easily. Promotion takes a long time. There are one to two product managers to a whole engineering team so engineers have an easier path to promotion and management. As a PM, you're taking on the role of being a leader just by saying, "I want to be a product manager." You're saying out loud, "I want to be the one making the decisions, and scope, defining what we're going to build, and leading a team that's going to build it." You have to have that cross-discipline leadership to also understand. I think [the conversation] helped me. 

What was your first conferred leadership role? Did you seek it? How did that happen?

Oh, yeah. I sought it. I have always been very clear about what I wanted to do. There were two points. So as an engineer at Microsoft, I was there for almost five years, full-time. I didn't have direct reports, but I did start to take on a lot of initiatives where I would report out to executives. We had a testing team in East Asia so I took on kind of leading them. They didn't report directly to me. They had their own managers that were local to them. I was the one that kind of was like, "Okay. Here's our goal. We're going to report out on this." 

Then, once I moved into product management... It was a really long time. I had been titled director at a couple of start-ups, but I never actually had reports because start-ups just don't hire that many people. Right? 

The first time, I think, the title actually meant something beyond just a title from a vanity perspective, was at Akamai. I got promoted to product line lead, and I had some reports. The first time I had a portfolio of products as opposed to, "I have one product." You kind of have to think about the broader strategy. You have to delegate to people on your team, "Who's going to own this," and make sure you've communicated that strategy and your vision to them. Then, give them the room to also add their own flavor, their own opinions, and the data they've collected, and take feedback from them if they think your vision is wrong. That's always fun. Yeah. I think that was the first time that happened and that was, gosh, five years ago now.

Did the weight of leadership feel any different? Being an IC versus being in this conferred titled role?  

I think it did. (As a leader) their careers, their understanding of leadership, that all starts to fall on you. Whereas, when you're not titled, you're like, "Well, I'm taking care of myself." Right? "I'm okay. Someone else is doing their own thing, but that's not my responsibility.." You want to be a good colleague, but it's not the same. I think it's a little different when you have someone else's career, their life, their well-being... If you have to fire them, that's something that really impacts their whole life, or sometimes if they don't get a promotion that they want, the disappointment there, or if you have to move them to a different project. All of those things, I think, are added to the weight of leadership when you do have that actual title.

Yep. We also have to make sure we're being good stewards of the business so, again, people have jobs, so they can have their own lives. That can weigh on you as an organizational leader, you are responsible for that to some degree. It's not just the CEO, in my opinion, it's everybody. Every leader feels that.

Yes. Oh, definitely. It is not just the CEO. 

Especially now, I feel that weight much more. I mean, I'm setting the product strategy for our whole company. That's not something I do in a vacuum, by any means. I take a lot of feedback, and I make sure I'm aligned with the rest of the leadership team. That's certainly something where you don't want to whiff on setting the product strategy for your whole company. 

Then, you don't get a round of funding, or you don't get the usage that you need, or you don't hit revenue goals. There's a whole machine around building the pipeline, market leads, and everything. Ultimately, if people get in there and use the product, and don't like it and leave, that's on the product. That's a new weight I feel, even though I own a smaller amount of product from a square footage landscape than I did in my previous role, the impact is much more direct.

 I feel that much more than when I was a senior director at a publicly traded company. There's a CPO, and there are GMs, and there's a CEO, and while I owned a core set of functionality, I was one piece of a much larger puzzle in responsibility architecture.

I bet that it feels much more on you. I just realized. I think you’re the first product leader I've had on the podcast so it's great. I love that you're speaking directly to the weight of particularly what a product leader might feel. 

Yeah. Everyone's going to feel their own. I mean, gosh. I always say, "I could not be a salesperson."

I was just thinking of the weight of sales, too. Right?

Oh, no. I couldn't take it. Those are different muscles I do not have.

Yep, yep. Everybody has different muscles in those ways. Did you ever stop trying to be in a leadership role? 

The only time I can think of is when I did leave that first start-up. I was like, "I'm done with tech. I love fitness." I was like, "I'm going to go be a personal trainer and a group fitness instructor. This is my new life."

It was funny because I was thinking about this question ahead of this podcast, our conversation. I was like, "Oddly enough, that's still a leadership position." You're still leading your clients. You're leading your classes. While I thought I was maybe stepping away, I don't think I really did. Maybe this is just me, but I do feel like probably most people in leadership had those moments where they're like, "Forget this. I want to do what I want to do." We're human. Right? We have those selfish moments.

I think there are certainly some times when I've rebelled against leadership more subconsciously. I think that's where you end up in those moments like I had at that first start-up where my boss had to pull me aside and say, "Shape up or ship out." I've had those moments in my life where I've had feedback from other people I love who are like, "Your behavior is hurting us." 

In those moments I was just like, "I'm going to do whatever I want to do. I'm not worried about the impact.” Not that I was acting out. I think it can be more subtle. Are you not dealing with your anger, and therefore, you're being angry at everybody all the time. For me, one thing was I would overexercise and be over-tired. Then, I'm cranky all the time to everybody else. There are things like that where you're just not thinking about how you treat yourself, and how you are in the world impacts other people. Sometimes, we all probably subconsciously rebel in that way. You hope that someone loves you and cares about you enough that they can say, "Hey, this isn't amazing. You're an amazing person, and you should look at this."

Leaders need that support. My experience is people when they're under stress, explode or implode. I don't mean that they're screaming and yelling. I just mean that they put it externally versus other people sort of implode. I'm an imploder, which is also just as damaging. There's an impact there, too.

 You know? So as a leader, I tended to take it all in until I'm like, "Okay. I don't think I can hold any more of the world anymore in my hands." When I left Travis, I thought, "Do I want to be a leader again? Is this what I want to do?" I ultimately decided to go this path. It's great. I've not said I'll never be a leader again. But I do think a lot of us have wondered whether we wanted to do it again, or not.

I would offer, you are a leader. It's a different way, similar to when I was like, "I'm going to go be in fitness." Right? I don't know that I ever want to be a CEO. I don't know. Maybe, don't tell my investors that.

Yes. Same.

I think that (a CEO) is a different level and type of leadership, responsibility, and accountability. CPO, that's exciting to me. You had your experience at Travis. I had my experience at my first start-up. I think there are those times when it's just really hard. You have to step back and reevaluate, and say, "Do I want to risk that again?" You can make it through those hard times. Certainly, I think, it's sometimes kind to ourselves to take a break. It's always good to stop and reevaluate.

Yep. For sure. As we talked about at dinner that night, you're currently VP of Product at StackHawk. You weren't looking or even taking phone calls. What changed your mind?

I wasn't looking. The reason I took the call was they emailed me first, and they highlighted that Joni (Klippert) was the CEO. I was like, "Well, that's interesting." I'd reached this point where I had few other female colleagues. I was working with a company that specialized in mentors. They had nobody to match me with anymore. They would match me with a mentor and I was like, "The mentor had half the org size I did." I didn't have somebody I could go to and say, "I have this problem. What have you done before?" I wanted someone who was, as a mentor, a female. I mean, there were all sorts of male mentors I could speak to who had been in my position. I wanted someone who had a female perspective because it's different. I think it's good to acknowledge that, and whatever your sexual orientation is, or chosen gender is.. We approach things differently. At least, I can speak from a female perspective and being in a male-dominated industry. I wanted that [female mentorship]. 

So, that was number one. I was like, "Well a dev tools company founded by a female, with female CEO." I knew Victor Ops, which was where Joni had come from, and Victor Ops. I knew that they'd had a successful exit. I was like, "Well, this is all very interesting." I took the call, and I told them from the get-go, "I'm not interested in a start-up again." I wanted to learn more because of Joni. I said also, "I don't know anything about security." They said, "Well, just talk to Joni."

Just talk to Joni.

That was the beginning of the end of my time at New Relic. So, I spoke to Joni. Joni was like, "Well, just talk to my COO, Ryan." So, I talked to Ryan. Then it was like, "Well, just talk to our CISO, Scott." "Well, just talk to our head of design." Everybody I talked to, I was having flashbacks to that very special time at my first start-up. I was like, "Gosh. I haven't had this sense and this feeling in so long, but I know it. I recognize it." Then, the other thing that happened was I let myself realize that while I'd reached this level that I thought I wanted to be as a senior director at a public company, I wasn't happy. In your leadership training, you talk about the archetypes. I realized I was being forced into being in archetypes that were opposite to where my strengths are.

Right.

I don't know if people on here have done this. I wasn’t happy to be an organizational and people-mover archetype. That's not what I wanted to be. I took the role at New Relic because I thought, "Great, I can really impact strategy here." That's just not what middle management at a publicly traded company is like, and I didn't know that. So, now I know.

Speaking of the weight of leadership. I think one thing is to feel the weight when you're unhappy. "Is this a weight I want to be carrying? Is this a weight I have to be carrying, right now?" The weight of leadership can be joyful, too. It can be something that energizes you. It can be something that you honor.

That's what I just let myself kind of realize, "Yes. This is great money. I'm putting money away for my daughter and her future. I can provide for her, but what do I want to show her? Do I want her to see me upset at work every day because there's a good paycheck, and there's good stock and all of that? Or, do I want her to see me excited to go to work every day, and passionate about what I do? Maybe it's riskier, but what do I want to teach her about life?" I thought I was staying in this role that I was unhappy about, for her. When I kind of changed my perspective about it, I was like, "This isn't staying for her, at all. This isn't what I want her to grow up thinking she needs to do, and how she has to live life." So, I switched.

Now, my daughter sees mom go to work very happy every day.

What a powerful moment to say, "What's the lesson? What's the thing I'm trying to impart in my child, and what am I showing them?" I think that’s a really powerful reason to move, on top of the opportunity at Stackhawk.

Yeah. I think one led to the other. I mean, had I not liked the team, I would've been like, "Ah, whatever. I'm going to stay where I am." The fact that I liked the team had forced me into this... It was funny. I told the recruiter, "I feel like I've been on an existential journey to get to accept this offer. I thought I was done with start-ups, giving up all the benefits that come with working at a large public company that range from 401(k) matching to all sorts of things." StackHawk has very good benefits…Butou have to think through all of that. 

Ultimately the core moment came when I was on vacation with my family and I just broke down crying. I finally felt how unhappy I was. I let myself feel that and feel how great I felt when I spoke to the StackHawk team, and how excited I was.

I don't say any of this to knock New Relic. Right? It's a perfectly fine company. They produce great software. It just wasn't the right place for me. I think that as leaders it's good for us to understand, as well. Again, when we do have that presence, if we're unhappy, that reverberates out to everybody around us.

Right.

So, we should make sure that we're making choices. Everybody should. Obviously, it's a very privileged position to be in, to choose between two well-paying jobs. You know? You do have to have those moments sometimes. You have to make sure you're letting yourself feel where you are, and what your truth is.

Yeah. Being a leader is not the same in all places. At some companies, we have to shift into a different archetype or leadership style for those who aren't familiar with my model. Phase a business, start-up, size, what's the company doing at the time, industry, those are all different things that we have to think about. Being a leader at a dev tools start-up worked for me. Scaling start-up worked for me. I don't know if I could do that at another company. Maybe, maybe not. I think it really matters. 

So, what's the thing that you found hardest about leadership?

Yeah. Well, we spoke about responsibility, especially when you don't want it. Those times in life where you're just like, "I want to be selfish, and I don't want to have to worry about how I impact other people." I spoke about the responsibility, especially where I am now, being a small start-up, and understanding how much of the weight of the success is on me. That's one piece. 

Another thing that was very hard for me was making unpopular decisions.

Right? I don't know about you, but I was surprised by how hard that was for me. 

Yeah. I know you and I have similarities in this regard. It is hard to make unpopular decisions. 

It was hard for me to realize that being a good leader meant that I wasn't necessarily the most liked person in the room. It meant that maybe my team would disagree with me. That was hard for me to grasp. Part of being a good leader means someone isn't going to like you because you can't be a people pleaser. You have to be the leader. You have to stand as kind of that pillar and hold that foundation. Then, along those lines, which is slightly different from unpopular, but similar, would just be making hard decisions. 

You can make hard decisions that are popular, but they're still hard to make. Things about, "Where do we make investments? What do you say no to?" You can have a lot of great things going on, and you can't do it all, especially when you're a small start-up. That is an element of being a leader, that's hard. I think that it's something that you can address. You can prop yourself up. You're still going to have to make unpopular decisions. You're still going to have to make hard decisions, but you can create that support system for yourself with peers.

As you were saying, leaders need those support systems. My husband always says, "It's lonely at the top." He got into upper-level management at a very young age. All of a sudden his peers, then, reported to him. He was like, "Well, who do I talk to about stuff? Who do I go vent to about something because I can't vent to the people I did before." I know that I've spoken with a lot of leaders that kind of feel this.

The last thing is adapting your leadership to different situations and people. When I was younger, I was kind of a bulldozer. I was like, "My way, or the highway. I know what we should be doing. Why isn't everybody jumping on board? And, let's go," and not a ton of empathy or compassion necessarily. As I've gotten older and had more experience, I think that kind of naturally develops. Also, just understanding the nuance of, "Sometimes you do have to be strong, sometimes you have to be the friend, sometimes you have to give somebody feedback and how you do that. When and how do you lighten a situation with humor? When do you need to stay serious?" All that nuance about leading different people through different situations, I think is something that just... You have to have those times when you are in it. You're like, "Oof. That wasn't the right way to approach that.

You have to have the life experience yourself to be able to have compassion and empathy for people, and what they're going through in the situation, their process around whatever is happening. So, I think those are some of the other hard things.

What do you find rewarding about leadership? What's the best part about it for you?

Definitely when you see a positive impact. Especially if it's been through a difficult time, and you get to the end, and there's that light at the end of the tunnel. You see, "Wow. That hard work worked, or this product strategy was the right decision. Maybe it was a hard decision, but it was the right decision." Now, especially, when I have a team and they come to me, and they're like, "This is great." My sales team says they feel more confident selling the product because of decisions I've made, and things that the engineering team has been able to deliver this year. That's always amazing when you see that personal impact on people. As a PM, you talked about, in product leadership, you always want to see that customers love using your product, that you've made an impact for your users, as well, you've made their life easier.

When you think about direct impact, that's always, I think, one of the top things about being a leader. I think as a manager, when I see my employees grow, and when I see them... You always have to give feedback to people. Then, when you see them take and integrate it. You're able to support them. They move through it. Then, how proud they are of themselves. When you watch them grow, and then you watch them able to expand and take on more, and do more, and make more of an impact, and grow their leadership, that to me is kind of the ultimate. I'm such a people person so that's probably more important to me than the product.

Honestly, with StackHawk, and now being a VP of Product and another level up, it's great. I think I've worked hard to have a seat at the table, to be heard, and to be able to make some strategic decisions. Sometimes I just have to stop and be like, "I did that. You know? I'm here, and I deserve to be here." That may be another hard thing about leadership. Right? Knowing when you deserve to be there, and working through that imposter syndrome. 

Oh, yeah. Oh, yes. Yep. I think most of us have felt that (imposter syndrome).

When you do really acknowledge that you're a leader, and again, it's not an ego thing. It's just an acknowledgment.

From there, I think, to me, the process of learning and growing, and taking that feedback, and seeking feedback out, and seeking mentorship, and having that support system, becomes really important. It's an awesome thing about being a leader, I think because you can grow at such an accelerated rate. That, to me, is amazing.

I think back to that first conversation that I talked about, how I've used it throughout, and just how I continue to find lessons from it, and build from it. I got some tough feedback yesterday, in a meeting. Yeah. It's hard at the moment. I don't know if it was tough feedback, or whatever. I got some feedback. It was hard at the moment, but then a couple of hours later I'm like, "Okay. That was good to hear. I'm going to take that, and I'm going to remember that moment, and I'm going to do things differently going forward, immediately, and then also long-term." I also learned a lesson that I can help my team with, and make sure that I'm putting them in the right direction. I'm guiding them correctly. So, I think those are all awesome things about being in leadership.

Yeah. I mean, those are great. How do you feel about the weight of leadership today?

I think, now, I much more embrace, and honor it. I was always one of those people who could easily fall into, "Well, why bother?" I wanted to save the world. I wanted to save the whales as a kid, whatever. You just feel like, "I'm one person." People are throwing straws into the ocean, and turtles are inhaling them. I can't stop all that. I can stop using straws. For me, once I really took on the weight of leadership... Like I said, there can be joy in it. There can be happiness and excitement, and it's energizing. You understand that you have an impact as one person. This is something else I hope to impart to my daughter. Right? Maybe, you don't let your stuff spill out onto someone else. They take that, and they had a pleasant interaction with you. Maybe, they were having a tough day, and they take that and they talk to someone else. You never know how your presence is going to impact someone else.

Then, the chain effect that that has. I don't know. It sounds hokey, but to me, that really changed how I present myself to the world. Instead of feeling this why bother sense, it allowed me to feel like, "No. I can make a difference. I can make an impact." I may never see what that is, but I at least know that I'm going to go out in the world and be a positive presence. That's not going to hurt anything.

I strongly believe there's no neutral. If you're neutral, you're impacting the negative. 

If you can go out and just say, "I'm going to be a positive presence," it doesn't mean you don't process your emotions. It doesn't mean you stuff down and go out with a happy face all the time. It means you look at yourself, you process those emotions, and you're not just spilling them out on other people, whatever it is. You just go out and try to be a leader for yourself, lead yourself in the right direction, and ultimately you'll lead others. We're all leaders. We should all feel that weight. Again, it should energize you. You shouldn't feel burdened.

What advice would you give a leader who's feeling that weight, who's maybe wearing the weight of leadership a little heavy, right now? What advice might you give to them?

Build up that support system, and look at what do you need to carry versus what are you carrying? I've certainly had times in my life where I've carried all sorts of things I had no business, or need, to carry. Then, that skews your perspective of what that weight of leadership does feel like because it's not the true weight. It's like you just ran up a hill with a weighted vest on instead of walking your dog up the hill. Right? You’ve still got to go up the hill, but how hard do you have to make it for yourself? 

So, I think that would be the first thing, really examine, "What are you carrying?" Then, also, maybe it is just a really heavy time. Is it a moment in time? Right? Find moments of joy. Find times when you can take a break, set that weight down, and rejuvenate yourself. Then, pick that weight back up, and find a support system who, maybe, holds the weight for a few minutes for you. Sometimes, there are those times when it's heavy, but it shouldn't just be always like that. It should be momentary, or for defined periods.

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