Leading an Engineering Team Without Having Been an Engineer

Jessica Darensbourg, Director of Engineering, Mailchimp

There’s this idea that only someone who has been in an IC role can serve as a leader for others in this area. I don’t necessarily think that’s true. I was happy to meet Jessica Darensbourg who disproves this stereotype. I was even more thrilled when she agreed to talk about her experience as a Director of Engineering at Mailchimp. Jessica and I talked about how she got into leading engineers, how her background is an asset and the best skill she brings to her role. 

It's been a bit since we saw each other. We met in the lead dev San Francisco LeadingENG workshop.

Yes, yes. That was my first LeadingENG workshop that I'd done. So, I was very excited to be there, learn from other people, and meet you. Your energy was wonderful.

It was fun. It was such a great group. It's from that workshop I discovered a bit about your background and I thought, "Oh, I bet Jessica has a great story to tell people." And so, here you are. Can you just give a quick introduction to yourself?

I’m currently a director of engineering with Intuit MailChimp. I live in Atlanta, Georgia, but I'm a native of Louisiana. And so, I always call that home. I’ve been in the industry for over 20 years. Well, maybe more than that, maybe 30 years. So, giving away my age a little bit.

You're at MailChimp. What’s the area that you oversee?

Yes, so I am part of engineering where we're doing the core offering of marketing products for MailChimp. So, I lead engineers who develop our analytics and our automation products.

I learned during one of the breaks during the workshop, that you have an English degree and a minor in computer science. How did that degree come about?

I was very technical-minded so when I was in high school my dad wanted me to be a mathematician. And it's like, "You are very smart in math, you want to go through that. You're very technical, you need to be a mathematician." I was like, "I do not want to do that." So, I was like, "This sounds so boring to me." But what we settled on was computer science. So, now this was in the '80s. My university had a business route and a technical route, I mean a scientific route. 

I started majoring in computer science learning Pascal, Fortran, and Ada. I don't even know if people know what Ada is. I did not like looking at a blank computer trying to figure out and write code. Just coming up with that creatively, here's this problem, how do you solve it in code? I hated that. I was like, "I just can't do this." I had to use relationships to get me through it. I relied on somebody else who would come help tutor me. It was  like, "Please come help me do this." 

So I did two years of computer science. I went through all the calculus, and differential equations,math and computer science classes and after 2 years , I went to my honors advisor and said, "I can't do this anymore but I still want to get out of school on time. What do you have where I won't lose any credits?" That's how it started. I said, "I don't want to lose any credits." So she's like, "Well, there's this new concentration called technical writing. You are great in English. When you write, you understand. We can transfer your computer science and math credits to a minor, and you will have your major courses in English. You're getting ready to start major courses anyway, so you'll do your major courses in English."

I was like, "Sign me up. I liked that idea because I can write but I don't have to program that much." So I ended up with an English degree with a technical writing concentration. I had a computer science and math minor with courses in engineering and physics. I ended up being able to do an internship with IBM as a result. They were changing their air traffic control system back during that time.. So, yeah, that's what happened. 

That’s so cool. How did you get into leading technical folks?

When I graduated and got my first job writing user documents for IBM, I started moving up as a technical writer. I was eventually hired by a company called Computer Task Group, CTG, to be an online technical writer for their virtual visual basic query tool that they were building for their data warehouse for Delta Air Lines. And as part of that,while writing online help for the tool, I was talking to people and coming back to the SQL programmers and COBOL programmers, and translating, being that conduit of understanding and writing and explaining how the program worked. Being able to talk back and forth and being that conduit between business and IT, afforded me to be promoted to business analyst. From there I was promoted to manager. I probably had 15 COBOL programmers at one point at Delta Air Lines. So using my knowledge of technical writing, as a business analyst, and working with the programmers to deliver something for the business is how I came into management. Most of my career after that was mostly either management or business analyst, depending on what company I was at.

This is your first director role, you're at MailChimp. How did that role come about?

Most of my background until MailChimp, was in the business intelligence area, in data warehousing. So, I spent nine years at Delta Air Lines when they were building up their data warehouse, and then another 14 years at Carters building up their data warehouse. So, I was learning about that as really either as a manager or a senior manager, but still being that conduit. However, during COVID, when everybody was going through difficult times, I was laid off.

Yeah. It happened to a lot of people.

So I said, "Let me take this opportunity to see what company where I can be my authentic self." And so, because I was at two large corporations as a senior manager and understood how to mentor, coach, and be a coach's coach with the folks that I worked with, that translated well to what MailChimp needed in a director role. MailChimp was the first private and the smallest company I had ever worked for. The job posted was for a senior manager. I went through the entire interview process, and when they offered me the job they offered it to me as a director position.

I love that. How did you feel?

I was like, "Oh my God, oh my God, oh my God. This is wonderful." 

I had felt for a long time that I could be a director but I wasn't afforded the opportunity because some people thought that I couldn't lead technically. But MailChimp saw that vision in me. They saw what I brought to the table as far as leading people and knowing what needed to be done. That was just thrilling. I was like, "Okay great, and I'm going to be able to be my authentic self."

I was going to be able to learn, I was going to be able to use my transferable skills. Excited was an understatement. Then I got there and I had to build the team. So, that was the other thing. "We are hiring you. This is a new position, and we need you to build this team. We want you to do all of the hiring, and so we want you to learn the process but also want you to find the right people." So, that was great.

Was building a team from scratch a challenge that interested you?

I had not thought about that before. At all. What I wanted all in my career was someone to trust that I can lead, trust my thought process, trust how I lead, and allow me to be my authentic self. I thrive better when I'm not completely off on an island, but when I'm able to ask questions, and be transparent, but trusted in my decision-making. I knew when I was interviewing what they were looking for, but not that I needed to build this entire team. I didn't know that at the time, because of course at the time, I was only interviewing for a senior manager. So, I think they were initially thinking maybe one or two squads at the time.

How big is the team now that you lead?

I have four managers now due to reorgs. But the team that I built, I hired six managers and 40-something engineers. So, we had about eight managers at one time that, at various levels, reported directly to me. And then hiring engineers too.

How long did it take you to build out that initial team?

About five or six months.

That’s pretty fast.

Yeah, we were rocking and rolling, let me tell you. We had one team that was already there, then a couple of others that moved over. But hiring the managers, I didn’t want to reinvent the wheel. I asked, “What kind of things do y'all use to hire people? This is what I'm looking for." We put together diverse, very diverse interview panels. I mean, we were rocking and rolling and making a decision knowing what we were looking for. So it really worked out very well.

What’s been the hardest thing about leading folks where you haven't done the work before?

One of the things that, just early on in my career, was not only having done the work before but also the personality type. I used to say I am an extrovert in an introverted world. I’m an extreme extrovert. So, even when I've gone to career matching folks, they were saying — I don't know if you're familiar with the DiSC profile, but I was like, "Definitely I'm an I," which is that very extreme influential extrovert, and most of the technical folks were C's, very analytical, very opposite in my thought process. So, it's like, "How in the world have you survived in this environment?" And I was like, "Yeah, I'm an I in a sea full of C's." So the hardest part was learning how to communicate to technical folks.

Like I’m an I personality. What did the C person need from me? When they found out that I hadn't programmed before, it was making sure that I was credible. I mean, I have a technical background, and I did complex computer programming in college. I didn't like putting it on paper, I didn't like coming up with the code. But once the code was there, oh, I could debug the hell out of it. Find the problem, look into the onion, and solve the problem. So, that was just making sure that they felt, if they had any doubt, that once I started talking and being able to ask the right questions, get them thinking, and show that I understood, made it better. 

It was just getting over that first impression, or that assumption of, "Well, will Jessica be able to know what we're talking about?" And getting to realize that it was ok that I ask a lot of questions. I'm a technical writer by trade, so I'm going to ask. I'm trained to be able to ask questions until I understand.

That’s how I get confidence from the people I lead and the people who manage me. Other folks might say, "Oh, well I need an expert to be able to do that. I need an expert in this technology." You don't necessarily need to. I can sit in a room with a consultant and a vendor and know if they're trying to BS me with the technology. I mean, I can certainly work through what you are trying to provide "What is it that you're offering? What does this architecture do? What does this technology do?” I also know when to bring in the experts. So, I think that’s the hardest part- making sure other folks see me as credible.

It’s changing, but there's a belief in our industry that you have to have done the role to manage those people. I don't know if that's necessarily true. It's a stereotype and why I wanted you to come on, was to help begin to change that. 

I absolutely agree. When it comes to teams, the whole thing about embracing diversity is you also bring in different diversity of thought. 

As you progress as a leader, you’re not expected to code. But every team has to know how to collaborate, every team needs to know how to determine the depth versus the breadth of how you deliver. You have to know what’s the right thing to do. But whether or not we are going to choose GCP cloud infrastructure or AWS cloud infrastructure, I can still ask questions about what's the business value that we need. 

Two different things need to come to the table. It doesn't mean that it needs two people. I mean, that requires two people, but it doesn't necessarily mean that I can't represent myself in a meeting, and what's going on because then it's a high level, you're not going down the details like, "Do you think this will work?" Well, I have enough background to be able to say that. So, I agree, it's not necessary to have programmed whatever. I mean, engineers are learning new languages all the time. You got PHP and you gotta train them in Go, or you gotta train them in Java, you have SQL ... It's just all the same.

I talk with leaders all the time who say, "Oh, I have to hire and manage someone in an area where I've never worked before." Let's say COOs have said this to me, like, "I have to hire and manage someone in finance, or accounting, or legal, and I've never done that." It can shake their confidence. But you seemed confident that you could do it. It didn't shake your confidence at all.

No, it didn't because I knew I had the technical aptitude. I mean, as I said, I was great in math — I understood the concepts. My favorite class in college was philosophy logic. So, the logic part of figuring out something is what you bring to the table. If I don't know something I will Google it. I have the background to ask the questions. So, it's like hiring a finance person. If I was a COO and was going to go hire a finance person, then I'm going to say, "Well, what makes the best finance people? So, here are the things I need to look for in the best finance people. Here are the questions I need to ask to discern if that person's going to be right for me and this organization."

Then I'm going to have somebody that's really skilled in finance go do a technical interview with them. It’s the same thing I do with engineers. When I'm interviewing a manager or interviewing an engineer, I want to know how do you solve problems? How do you motivate your team? How do you treat people? How do you get along? If someone is not doing well, what are you going to do to help inspire and motivate them to be their best self? I don’t interview engineers at this point but if I did, I can ask someone else. Can they code? But what I want to know is, can you solve problems? What is your method and your thought process on how you solve problems?

That is something that I love and that's what I do all day. Every day growing up I loved to solve problems. Like I said, my favorite class was philosophy logic. Those problems, that was my M.O, for real.

That's so true. You’ve talked about some things you bring to the role like the ability to ask questions. What else do you bring from your experience that allows you to lead engineering teams? 

I always say my philosophy is I like changing the world one person at a time. I like being able to meet the person where they are, seeing what makes them tick and what they want to do. And bringing out and helping coach them to be their best selves. So, that's very important. I love to teach. 

I had a VP tell me I’m a good teacher. I like to teach and explain. But that comes from technical writing because you're explaining to people how to do something. And then just specifically where I am now, I've always worked with public companies, large public companies. When I joined, Mailchimp was a private company, small. We were just recently acquired last year by Intuit. 

I knew how public companies work. There were people that may have always worked with startups and small companies, and now they were going to go through this acquisition process and this change of what does it mean to work for a public company. What it means to work for a large company? How can I be as impactful, like the big fish in a small pond versus a small fish in a big pond, how can my work still be impactful?

So, being from two large corporate brands, I've been able to bring that knowledge and that kind of calming sense as well. This is how it's going to be, this is what the processes are, this is what we've been through. And I think that makes it easier for me, but also easier for them, and me to be able to help them get through this process. Because it's a change, and it's definitely a transition.

Right. You’ve already made big changes and you love helping people. When it comes to change we have to understand the structural side of change and the emotional side. You can help people go through that.

Absolutely. And I think that's one of the things where even every time we would have team building classes with my other companies, it always comes out like I'm the only one of this personality type in the room. It gave me more confidence when they pointed out, "These are the people you need in the room because (of their personality).”

So, those are the people that, when you're talking about a change, they're going to think about how this is going to affect the people? How is this message going to come across? How are you communicating, and when you change how is that going to affect them and maybe give some ideas differently? I find myself doing that all the time. I'm like, "You know you said that but this is how it's going to come across. Might want to change that," or like, "Oh, I'm getting that emotional aspect. Let me kind of talk you through what this means and why." So, that's the part that I love, because I love helping people.

Right. You can help them in that way. It's interesting because my dad's an engineer, my husband is an engineer. I have a ton of friends who are engineers. People ask why I hang out with engineers so much. I find that we have complementary skills. The complementary things that we bring to each other can make us even stronger rather than all being the same.

Yes, yes. I mean, the engineers are visionary, they're creative. The engineers are why we have the medicines that we have today, and why we have all these different railroads and all these other kinds of things. They're very passionate people, passionate about what they're doing, passionate about their craft, and very highly collaborative about what they're coming in. So, that's what kind of makes it very compatible. Admittedly, I didn't necessarily know that from engineering because I had SQL developers and COBOL developers that wanted to go into their own world. "Nobody talk to me. You want me to code, I'm just going to code this. That's fine." And engineering was different. It's like, they have pairing, we worry about team health, we talked about the collaboration, they have their Slack channels and how they communicate, and going back and forth and talking.

And that was surprising to me initially. I didn't think about it but then I realized the person that hired me, and I think about what she knew and when she was talking to me, and then I'm like, "Oh, that's why I'm a good fit. That's why I can come in and help understand what they need to do." But I didn't necessarily know that till I got in. Just being able to connect the dots on how I fit in was cool.

What advice might you give to leaders who don't have discipline expertise with those that they're leading? 

You might not have disciplinary expertise, but what passion do you bring to the table to lead? If something is your passion, then it is being able to be vulnerable and transparent about what you know, but really what you don't know, and help. I just had that conversation with someone. I just hired a principal engineer. I told him, "Look, I'm leaning on you to help me with the new technical architecture that we know we need to do.. If there is a time when something that's coming out of my mouth technically doesn't make sense, I give you very much permission to say, 'Jessica, this doesn't make sense."

So, it's just being vulnerable. I’m transparent. I give them permission. “Tell me what you think, I’m going to accept what you say. And if something isn’t making sense, tell me why.” Other advice is to ask lots of questions and be confident. You're there for a reason. Somebody chose you and saw something in you for a reason. Just like the person, Alianor, that hired me. She saw what was in me, what they needed. You're there for a reason. So, just embrace that but be vulnerable and transparent about it.

Vulnerability is hard for a lot of leaders. I love that you lean right into it rather than trying to fake it until you make it.

Yeah. It's a balance because you never know, not everybody has the best intention, so you never know what their thought process is. I had someone tell me one time, "I don't know if I would want you to be my counterpart as an ENG leader making technical decisions if I know that you don't have that technical background." I was like, "But you only know I don't have the technical background because I told you. What would've happened if I was in a room, you didn't know, and I'm able to do that?" 

Part of being vulnerable is being aware of your audience. Not hiding it or anything, but knowing just the same way in your private life as you don't share everything, there are some things you decide what you share and then you go back and learn. Be your authentic self and have boundaries about what you share and what you don't.

So, it's like with this principal engineer, so I'm making sure that I understand the background but if I know the context of a meeting, I'm making sure that somebody has prepped me on what I need to understand, what I need to do, what I need to look out for so that I'll manage my audience effectively. So, it's not everything, but it's just a balance part of why you don't have to fake it. 

It's like I used to tell my son, it's like you don't share your whole world, your whole thoughts with everybody, but you do share it with the people who you know that can help you, and who you need to help you. Not who you know can, but also who you need to help you share that. My job is to help them be successful, and their job is to help me be successful in helping them. They help me help them.

I want to pull out what you said about knowing your audience. It's so important for leaders to know their audience and adapt their communication. It’s true whether you lead people where you have expertise in their discipline or not.

Yes, absolutely. And that doesn't come easy or without challenges. One of the things I think helped me to be successful when I was looking for this job is realizing that I needed coaching. I started with a career coach helping me find a job and pull out my authentic self, and helping me transfer my skills. Now she is a leadership coach for me. I didn’t always know I needed a leadership coach. It's being a continuous learner and being willing to be vulnerable and help someone coach me. So, we'll role-play, we'll practice, I'll share things, what's going on. She helps me get more confident and helps me be able to process and think about how to lead. 

If you're (feeling) unsure, hire a leadership coach. I was fortunate that most of the time, the company paid for it but other times they didn't. So, it's an investment in myself to always become better, and be a constant learner.

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