Lead(H)er Profile - Jennifer Armstrong, VP of Engineering at Duck Creek Technologies banner image

Lead(H)er Profile - Jennifer Armstrong, VP of Engineering at Duck Creek Technologies

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Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Jennifer Armstrong, VP of Engineering at Duck Creek Technologies.

Where did you grow up and how would you describe yourself as a child?

I grew up in Lake Zurich, Illinois and I would describe myself as a quiet tomboy. I had two older brothers and a younger sister (who was 8 years younger), so I pretty much grew up with boys at a young age. I would play different sports or was running around outside until it got dark. I thought if my older brothers could do it I could as well. Which lead to a few injuries but also a fundamental belief that nothing could stop me if I wanted to do something.

What did you study in college and what was your first job out of school?

When I was growing up, I was always interested in the STEM classes. I knew I would eventually be focused on something in that space. When I started at DePaul University in Chicago, IL, I wasn’t sure if I wanted to study math or computer science, but I eventually settled on computer science, but took a lot of math classes for fun. I eventually graduated with a bachelor and master’s from DePaul in computer science. 

My first job out of college was as a consultant at a boutique consulting company where I worked for a few different insurance carriers over 6 years. This started my long journey in the insurance space. I always like to say that my soul is technology, but I grew up in insurance.

Can you share the details on your career path and what were the critical moments that got you to where you are today?

The first critical moment was when I decided to take a leap of faith in my abilities as a technologist and move from a role where I felt comfortable, I knew well, and I was an individual contributor with minimal responsibility. To a role that was in a space that was functionally and technically new to me. In addition, I would be leading a team of eight people. The project was an overhaul of a critical system purchased from a vendor that then could be customized for our company. Our job was to learn as much as we could from this vendor to become the experts but also lead this software design going forward. It was a lot of hard work, long hours, but I learned more in one year not only about this software but, more importantly, what I was capable of. I learned that I really enjoyed and was good at understanding the bigger business problem and coming up with the solutions for this problem. It allowed me to grow in mentoring or helping other engineers to guide them in their journeys.

Jennifer Armstrong Duck CreekThe second critical moment of my career was assessing my work life balance and realizing that I couldn’t sustain 70+ hour work weeks and attain the goals that I had both at work and in my personal life. I decided to leave a company that I loved, had great co-workers, and was advancing in my career, to an environment that I was able to truly balance my career and my personal life. After this change, I was able to focus on me, and I got married and now have three wonderful children who are my heart. My family has taught me a lot of good life lessons on compromise, patience, and most of all that you just need to roll with whatever comes your way.  The career change also allowed me to move to a company where I was able to leverage my strong core principles but grow significantly in my overall engineering leadership skills, influence without authority, and customer communication and presentation skills.  

What is your current role and responsibilities?

As VP of engineering at Duck Creek Technologies, I lead teams of over 120 engineers for some of our core products. I am engaged in all aspects of delivering product releases and service ownership of the products.

Looking back, is this where you thought you’d be professionally?  Was it always your goal to be in this position? 

This simple answer is no. When I finished my masters, I had fully intended to finish my PhD in computer science and be a professor. I loved being in the academic world. If I didn’t go into academics, I figured I would be a coder for my career. I was and still am an introvert, so being in a position where I had to interact with people constantly was a very uncomfortable concept. I learned that just because I am an introvert doesn’t mean I have to limit what I am capable of. I always mentor people to take a risk on yourself and don’t limit yourself on your or others’ preconceived notions of what you can do.

For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?

First, define your brand. Who and what do you stand for as a professional? Whether it is technology, the ability to communicate well, the ability to see the bigger picture, negotiation, etc.  Your brand will change over the course of your career as new interests are found or new talents are honed. Your brand will help you in any career path you take as it is the foundation that you can fall back on and lean on.

Second, find a good mentor(s) that you trust to help you on your career journey. A mentor doesn’t always have to be someone you have a direct mentorship relationship with. I have had people that I would consider mentors that I just watched how they interacted with people or handled situations. Everyone in your life/career can be a mentor informally. It is also important to find advocates for you outside of your direct management chain.

What are the most important skills that you need to do your job well?

The skill that helps me the most is asking questions. Most of the time people will tell you what they want and not necessarily what they need.  I had someone tell me early in my career to ask the 5 whys. If you ask why 5 times, it will get to what someone truly needs versus what they want or think they need. Asking questions allows me to fully understand a situation where I can make the most educated decision I can.

What do you find most interesting/rewarding about your work?  What’s the most challenging?

The most rewarding thing about my work is seeing an idea come to fruition. Watching a simple idea get designed and built out and users start to use it. In insurance, knowing that things I am involved in have a direct impact on companies that their job is to return a person/company life back to normal after an event.

What is your proudest professional accomplishment?

One of my proudest moments was when we were able to successfully roll out the overhaul of a major critical software at the company I was working at. It changed everyone’s ability to service our customers. The other moment was being involved in building out a program to foster and encourage innovation. In technology, innovation is critical to continuous improvement. This problem was a catalyst to change the innovation culture.


What do you enjoy doing in your free time?

Spending time with my family, Friday night pizza and movie nights, cooking, reading, traveling, and girls’ nights out with friends.

Jennifer Armstrong Duck Creek

How do you manage stress?

I don’t stress a lot, but when I do, laughter helps. So, I will do something that just makes me happy and laugh and I can usually manage my stress levels.

How many cups of coffee do you have in a day?

Probably around three, but nothing past noon otherwise I won’t sleep.

What advice do you have for recent college graduates?

Find what you enjoy doing. You will spend a decent amount of time doing it and if you really enjoy what you are doing in your career, opportunities will become available to advance in whatever ways you want. The second piece of advice I would say is believe in yourself and it is OK to take a risk or leap of faith. If something doesn’t work out, there are always other options.

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Duck Creek Technologies gives P&C insurers a genuine path to the future.

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