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Pivot! 7 Women on the Career Changes That Have Shaped Their Trajectories

‘Life is short, and we spend most of it working. Why have one career?’

Woman taking a course to change careers
Photo courtesy of Jason Goodman

This article is part of InHerSight's Career Trajectories series. Women's career paths vary significantly. Hear from women themselves about the pivotal career decisions that have shaped their growth and success.

How old were you when someone first asked you what you wanted to be when you grew up? I honestly can’t remember, but I know I didn’t have a good answer to that question until I was in my mid-20s. Even then, I was very aware that many of the jobs I might hold likely didn’t exist yet. Growing up alongside rapidly changing technology meant I, like you, witnessed new roles and industries pop up seemingly out of nowhere. 

That didn’t remove the pressure I felt to find a path and stick with it, however, and many of the women I’ve spoken with have felt the same way as they’ve navigated their careers. The prevailing mindset around career trajectories is that they should be linear: you decide what you want, you get a degree (maybe), and you follow that path until you retire or you inherit a large sum of money from a long lost relative. Whatever happens first.

If that straight-and-narrow mentality works out for you, great. You’re a rarity and, honestly, quite lucky to have figured out what you want so early on. 

But for most of us, a traditional career trajectory simply isn’t in the cards, and that’s okay. The average person will change jobs 12 times over the course of their careers. And women? Well, 73 percent of us want to change careers entirely. A large number of us do.

Throughout 2022, InHerSight will be featuring stories of women’s diverse career trajectories—ladder climbing, career breaks, entrepreneurship, careers without degrees, and more—to show you just how unique your path can and will be. In this first installment, we spoke to seven women who’ve changed careers multiple times about how they got where they are and, most importantly, about embracing change.

My favorite quote? “Life is short, and we spend most of it working. Why have one career?” Why, indeed.

7 women on the career changes that have shaped their trajectories

Koma Gandy

Vice President, Head of Curriculum at Codecademy

What do you do?

I lead and manage a team that creates high-quality interactive educational content that prepares our learners for rewarding careers in technology.

How did you get where you are?

I was a midshipman in Naval ROTC at Harvard University, so my first "job" was as an officer in the U.S. Navy. (I was part of the first groups of women assigned to combatant ships and was the first woman assigned to my first ship in its history).  

After a little over four years on active duty, I transitioned into the Navy Reserve and took a role in the private sector doing information security/cybersecurity work for the Department of the Navy at Booz Allen Hamilton. In 2003, I was recalled to active duty and deployed to the Arabian Gulf at the beginning of the Iraq War for several months.  

I returned from deployment, and then decided to pursue my MBA at Georgetown University. After graduation, I pivoted into financial services after a brief stint at The Cohen Group providing consulting expertise for firms involved in aerospace/national defense. I moved to New York in 2007 and started my career in financial services at an asset manager, where I had to teach myself and learn on the go about investment management, hedge funds, and financial operations.   

After a career gap in 2009 due to the financial crisis, I took a role at EY in their Advisory practice using what I learned to work with large asset managers and to help them solve their operational problems. I moved on to Morgan Stanley in 2015, and after getting an opportunity I couldn't refuse, I joined Codecademy in 2019. I have always applied the lessons of leadership and management I learned very early in my career to be successful in different industries, and consistently sought out opportunities to solve problems that make an impact.

What has most surprised you about your career?

It's been incredibly non-linear, but I wouldn't trade the breadth of my experiences for anything. I never thought I'd find myself working in finance, or making another pivot at this stage in my career into tech. I've learned so much about myself and different industries on this career journey, and I'm thankful for the colleagues and friends I have made along the way.

Kait Heard

Manager, Talent Acquisition and Strategy at Milhouse Engineering and Construction Inc.

What do you do?

Now, I am a manager of talent acquisition and strategy. More often than not myself and the talent team are called “recruiters” or assumed to be “just recruiting,” but talent acquisition is so much more than recruiting; it is stakeholder management and engagement, it is forecasting future needs and building a strategy to prepare for what's to come, it is learning market trends and ensuring we stay competitive, it is brand awareness, it is building and nurturing our candidate relationships and above all it is cultivating a culture of excellence. 

Talent acquisition professionals are not your admins. We are your business partners here to help you build success through people and culture.

How did you get where you are?

Due to a combination of an opportunity awarded to me and my willingness, effort, business acumen, and genuine attitude, I was able to move from Australia to the U.S. to pursue my career abroad. This led me to amazing people who have shaped myself and my career, furthering my education at night school at DePaul University and ultimately taking a leap of faith after five-and-a-half years with my previous employer to diversify my experience through new exposure, new learnings, and new corporate endeavors. I have now learned more than I ever could have imagined, and I owe that to taking risks, challenging myself, and stepping outside of my comfort zone.

What has most surprised you about your career?

How much I have been able to achieve outside of the "norm." Meaning, my journey has been untraditional and did not start with a business or HR degree. I put one foot in front of the other with the best of intentions and hard work at the forefront. To find myself living in Chicago, collaborating with C-suite leaders from all over the world, and aiding in the development of those around me would have surprised my younger self, while today I know I am deserving of the career I have made for myself.

Jessica Lam

Engineering Program Manager at CrowdStrike

What do you do?

As an engineering program manager, I lead project teams consisting of developers from various different disciplines to produce solutions and enhancements to our end point products. I am responsible for ensuring the proper conversations are being held, decisions are being documented, and strategizing when future work should be implemented.

How did you get where you are?

I went from administrative assistant (finance) to customer specialist (banking) to business analyst (banking), to project manager (banking) to product manager (banking) and finally back to program manager (information security). I read job descriptions and tried to find opportunities in my current role to gain some experience to apply later. I also studied and obtained my PMP to open opportunities for project management.

What has most surprised you about your career?

Relationships matter. I only had one opportunity that I obtained from responding to a job ad. All other transitions had been through my relationships. Also, that opportunity is everywhere, so you need to be prepared. My biggest transition was from being a customer specialist to business analyst, and I landed that opportunity at a social setting because I had my resume on my phone

Jaime Allpress

Agile Process Leader at Alley

What do you do?

As an Agile process leader at Alley, I coach and support my team through facilitating communication, problem-solving, making work visible, and encouraging ongoing experimentation with ways to streamline our work and gain efficiencies.

How did you get where you are?

As an account manager for a small digital agency, I learned the basics of web development, project management, and building client relationships. My next role, as a business analyst, started my Agile journey and gave me hands-on project experience as part of a development team. I learned how to break project deliverables into user stories, write acceptance criteria and test cases, and map out technical processes. Becoming a certified scrum product owner presented me with opportunities to grow and expand my skill set further. I led project discovery for large, cross-team projects, created roadmaps and release plans, negotiated with stakeholders as needed on projects, created and led Agile workshops, and trained new product owners. Along the way, I attended many conferences to expand my knowledge and my network. My current role as an Agile process leader at Alley allows me to synthesize all the tools I've added to my toolkit along my journey.

What has most surprised you about your career?

My career growth has been propelled by a love of learning and growing, and each experience has led me to the next. Most surprising to me has been learning that with so many opportunities available, a strong work ethic and sense of wonder can open many doors!

Kelly Gebo

Associate Director at thoughtbot

What do you do?

As an associate director, I am the first in a role dedicated to business development and marketing efforts for our thoughtbot teams. I also play a large role in optimizing client relations and sales processes.

How did you get where you are?

I spent time thinking through my talk track when elaborating on my experience. For example, I have a unique major and have spent time at companies of varying sizes, both in B2B work and agency work. At times that made me feel like my journey wasn't coordinated but now I think it gives me a unique background. I took time to plan what I learned each step of the way into a cohesive story instead of just a quick summary.

What has most surprised you about your career? 

At moments my career change didn't feel planned, but in reflection on how I've handled it, it's all helped to grow my unique experience and skill sets.

Eudora Linde

Scrum Master at Penn Interactive Ventures

What do you do?

I'm a people organizer and blocker remover; I make sure engineers are unblocked, are staying on track to hit deadlines, and track several data points so we can have a crystal ball reading into the future of what our capacity may be. I am also a keeper of process for the two teams I work with.

How did you get where you are?

My degree is in journalism, and I spent a few years as a local news producer. I always loved writing, but was getting burned out from all of the sadness in the news industry—so I pivoted to working as a copywriter at an agency, and LOVED it. A boss saw my potential, promoted me to project manager, and I began my path toward a scrum master.

What has most surprised you about your career?

If you had told a 22-year-old, freshly graduated version of myself that I'd eventually be working in tech, I would have laughed. I never initially thought this is where my path would take me, but I love it!

Elisa Verna

Developer at thoughtbot

What do you do?

I'm a software developer for thoughtbot, a Ruby on Rails consulting firm.

How did you get where you are?

At 20, I started a graduate program with the goal of going into academia. I quickly learned that it’s not much different than corporate America, so after getting my master’s degree, I got an editorial job at a magazine that reviewed romance novels. After several years in publishing, I did a coding bootcamp and convinced a small start-up to hire me as their first engineering intern. Five years later, I’m building software for all kinds of clients.

What has most surprised you about your career?

The most surprising thing has been how impactful solving people and process problems can have on an engineering team. Soft skills are like gold. I’ve met with engineering managers who could barely stumble through a serious conversation—and their job is to manage people! If you’re not talented at algorithms or feel self-conscious about your technical skills, leverage what you’re good at, and it will take you far.

Margaret Schneider

Customer Value Manager at CrowdStrike

What do you do?

As a customer value manager, I collaborate with field sales team members in account retention and growth with quarterly executive business reviews and value realized analyses. By developing a comprehensive understanding of their goals, objectives, and pain points, I support Crowdstrike customers in driving toward outcomes.

How did you get where you are?

After my college graduation, I started an analytics consulting firm where I helped small businesses manage their digital strategy. I realized I needed a broader business background to create a deeper impact, so I applied for and graduated from Rice Business MBA. After my MBA, I became a strategy consultant at Gallup and later at ZS Associates, helping companies in transformation. Then, a Crowdstrike recruiter called about the hyper-growth opportunities in cybersecurity and my current team.

What has most surprised you about your career?

Developing your ability to communicate and set expectations is potentially one of the most important parts of your role, no matter the industry or job title.

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