Kjersten has 14 years of experience in the software industry, with over 5 years of fintech/insurance focused engineering experience. In her time as Head of Engineering & Product at CoverHound, Kjersten has successfully launched CyberPolicy and Coverhound Business Insurance.

  1. How has your life experience made you the leader you are today?  

Growing up, my mom was always the main breadwinner in the family. She grew up on a remote farm, got scholarships to pay her way through college, started working as a file clerk and was gradually promoted up to the executive level. In school there were always programs to encourage women to do more but my mom’s example gave me the belief that I could achieve almost anything I put my mind to.


  1. How has your previous employment experience aided your current role?  

I became an engineer after working in other roles at tech companies. Like many engineers, I feel a pull toward creating a robust technical solution for every problem, which can lead to over-engineering. A strong focus on business goals helps me avoid this and encourage a balance between engineering and business needs.


In my current role at CoverHound, I try to bring an engineering mindset to business discussions. Since engineers spend so much of their time building things, they start every subjective discussion (e.g. the pros and cons of various changes) by making sure that everyone has the same understanding of facts, for example how the system works. There are a lot more subjective topics on the business side and planning discussions can break down if people are operating with different views of the basic facts. An engineering mindset can help you identify when that’s happening and get people on the same page.


  1. What have the highlights and challenges been during your current role?  

The most gratifying part of being a manager is giving people new opportunities and watching them learn and grow. I’ve had the privilege to work with amazing people at CoverHound who are doing a fantastic job and headed for even greater things. It’s inspiring to know them and have some small role in their story.


Learning to be a better manager is a constant challenge. You hope you’re putting people in the right positions and giving them enough support and feedback. When that’s not the case, it has a big impact on people’s lives and that’s rough.


  1. What advice can you offer to women who want a career in your industry?  

Coding schools are a great way to get the experience you need to get that first job as a software engineer, you could have a job as a software engineer in a matter of months.

Another option is to learn on the job. I started ‘programming’ with Excel and was automating parts of my job ever since I was a temp administrative assistant. From there, I worked on more complex problems – writing scripts to transform and load data. Eventually I was asked to start contributing to the code base. I know a lot of people who got started updating web sites. Everyone’s path here will be different – the important thing is to start solving simple problems, build up your technical knowledge over time, and progress to more difficult tasks.


  1. What is the most important lesson you’ve learned in your career to date?  

When you’re deciding where to work, it’s important to look for a place that’s going to give you opportunities to grow and great people to learn from – I have been lucky to find that in my role at CoverHound.


  1. How do you maintain a work/life balance?  

For me, the trickiest part of work/life balance is to stop thinking about work all the time. Meditating is by far the best way I’ve found to deal with this. It helps me relax and get out of my own head.


  1. What do you think is the biggest issue for women in the workplace?  

Asking for what they want. Women often don’t want to seem needy or demanding so they don’t ask for the opportunities and responsibilities that they’re interested in. Part of this is proactively asking for feedback about what you need to improve to get that position. If people don’t know that you want something, they’re unlikely to give you advice about how to do a better job at it.


  1. How can we encourage more women to start their own business?

The VC funds that focus on women-led companies are taking the right approach. We need to make it financially possible for the women who already want to start their own company to do so. There are probably a number of unconscious biases that are making it more difficult for women to receive funding. As it becomes more common, those biases will change and there will be a better network of women founders.


  1. How has mentorship made a difference in your professional and personal life?

I’ve never had a formal mentor but I’ve picked up different things from different people. If somebody’s good at something, I pay attention to how they do it and see if I can incorporate that approach into my own life.


  1. Which other female leaders do you admire and why?  

Sandi Metz has so many great insights about code quality. It’s an unglamorous area of engineering but it applies to all developers, regardless of their specialty, and it makes a huge impact on productivity. She explains complex and subjective concepts in a way that’s clear, concise and relatable. She’s amazing.

Sheryl Sandberg, of course. She’s accomplished so much and she doesn’t need to put her personal experiences out there and make herself vulnerable but she does it anyway. Lean In is full of great advice and so validating. There are parts of that book that I think about all the time.


  1. What do you want to professionally and personally accomplish in the next year?  

Now that I’m working with the engineering team again, I hope to get more hands-on with engineering problems. I’ve enjoyed the architectural discussions we’ve had so far and I’m looking forward to a lot more of them!


  1. What are the top three tips you can offer to an entrepreneur starting out?

I’m sure somebody who has started their own business will have a lot more insights here than I do but here are my thoughts:

  1. Have a clear idea of what you want to accomplish but also what is going to be different/unique about your business.
  2. In addition to a big hairy audacious goal, set up milestone goals to keep the team motivated.
  3. Negative visualization techniques are useful both to manage stress but also to plan for all possible outcomes.


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