What I’d say to me back then – CircleCI’s Jane Kim on being bold enough to make a scary mid-career change

When Jane Kim decided to switch from an established career in banking to technology, it was no easy task.

After majoring in economics, Kim joined Goldman Sachs in 2002 in an investment banking role, and then moved to the buy side, sourcing her own pipeline and closing multimillion dollar investments.

This was at the time of the Great Recession, and Kim wanted to broaden her exposure to different sectors, and make a change from sales and deal making. Seeing the growth of the technology industry in the 2000s, she decided to transition across. But her plan initially faltered. Kim explains:

It was terrifying. I didn't get a lot of interviews to start because I didn't have that background. It was a very big change. Not having those experiences, not knowing what skillset I needed was hard.

Disrupt your career plan

When Kim first started out in her career, she had a firm one-, five- and 10-year plan. Disrupting that drove a lot of uncertainty, especially with an established career behind her when she decided to move over to technology.

Having to force myself to see myself in a different way or see different new opportunities, and working in that unknown, was hard.

Kim has now built a career as a sales leader in technology, despite never being a tech sales rep herself.

I was a sales rep in finance, but not in technology. That's still something I have to talk through because I wasn't ever in the exact same role as the people in my team.

Initially that was a barrier, both from an employer standpoint, hence the difficulty getting interviews; but also for Kim herself, trying to think about how her past experiences met the requirements of a new industry, and her willingness to learn different technologies and skillsets to position herself as a great candidate.

I'd tried to cast a wide net and as difficult as it was to find the position that I thought would be the best learning opportunity, I'm glad that I did because it opened up not only new opportunities, but a completely new career path for me.

Kim’s first role in tech was in business operations at SuccessFactors, where she had the opportunity to work directly for the CEO on strategic projects. She then transitioned back into sales, but this time in a management position. When SAP acquired SuccessFactors, she became Global VP of Cloud Corporate Sales.

A year later, Kim made another transition from large enterprise to tech start-up, joining Optimizely as VP of North America, and then CircleCI, where she’s now Chief Revenue Officer (CRO).

The move to a start-up was more about the opportunity for a new challenge, rather than issues at SAP, she notes.

In any job, as long as I'm continuously learning and able to take on new and different challenges, that's what keeps me motivated. Going from a large conglomerate, it was a great learning opportunity but it was a much more established company, learning the processes they have and the way business is done there. Moving to a start-up is an opportunity to build that and there's no greater challenge. With start-ups, there are a lot of new challenges and growth opportunities, but potential pitfalls and changes in the market as well.

Representation equals diversity

Looking back on her early career, the biggest change Kim has seen for women is representation. As a Korean American woman, there weren't a lot of people that looked like Kim on her team, and definitely not in a leadership role. This was the case in both finance and enterprise software sales.

Without that level of representation, I didn't feel as much that sense of belonging or part of the team because I didn't have the same level of connections or shared experiences that my white male counterparts did. There were times because of that, it felt lonely in my career in the earlier stages.

Kim was fortunate to find mentors who saw her potential and helped cultivate her career, even without that level of representation. And now, Kim sees a lot more women and people from underrepresented minorities in sales and leadership.

It still isn't easy to establish your career as a woman, but the more that we have women on teams at the highest levels from a professional standpoint and leadership positions, that can better encourage other women to join the field.

As CRO at DevOps specialist CircleCI, Kim sees fewer women in this field. She puts this down to it being a very technical field with a technical audience, meaning a lower level of exposure and understanding. She’d like to see this change.

Rather than looking at the technology itself and being intimidated by it, it's about can you grow passion and have an interest in the customers that you're trying to serve. Ultimately, it's about trying to understand the business goals and challenges that your customers are facing, and how you can help them.

Having said that, CircleCI absolutely is the most technical product and market that I've been in. There has to be some level of interest and willingness to learn.

To increase diversity in the business, CircleCI is working to build a robust pipeline of female candidates and candidates from underrepresented backgrounds for all roles, especially management. This involves dispelling any unconscious bias in the interview process, and ensuring the firm is creating a great candidate experience from the get-go.

To counter a potential lack of exposure to the technology among more diverse candidates, CircleCI looks for people with a strong sense of curiosity and willingness to learn, and assures them they will be supported in developing the required skills and technical expertise.

Return to work

One of the main barriers for working women is returning to work after a career break, often after having children. This is something Kim has experienced first-hand very recently. Her son is now six months old, and she has just returned from 12 weeks’ maternity leave.

It was an incredible experience to be able to take family leave in order to bond and care for him before returning back to work. One thing companies can do a good job of, and one that I'm grateful to CircleCI for, is the family leave policy that we have, not just for birthing parents but for all parents and caregivers.

It’s good to normalize taking these breaks and demonstrate how it isn't detrimental to one's career. I've had a number of women across the company tell me they appreciate seeing an executive take time off, but also come back so motivated to step back in.

Kim’s transition back into the business was a smooth one, something she attributes to both her being proactive and building the right coverage plan, but also the support of the company.

It was a couple of months transitioning back in, and now I've been back in work for almost two-and-a-half months, I feel like I’m back up to speed.

Juggling having a child with being back in a high-pressure job is something Kim is still trying to navigate, but she feels the support from the company, other executives and her team.

Sharing her experience with the rest of the company is important to Kim, so she can contribute to building this inclusive culture, and showing other parents what it would be like for them to take leave and return back to work.

I try to be very open about the ways in which I'm trying to balance my life, the ways in which I’m continuing to drive our business forward, sharing both how it’s challenging but also how fun and how exciting it is for me.

Uncertainty is opportunity

Thinking back to the start of her career, Kim says the one piece of advice she’d give her younger self is embrace new opportunities. Making the transition from finance to tech was scary and difficult at the time, but those moments of turbulence and uncertainty are better viewed as opportunities to build different skillsets and get different experiences.

Sometimes the most interesting career moves are the ones that you make for yourself. I'd love to tell myself to be more open to new opportunities, even if they seem to deviate from your planned career path. Sometimes, that can be the most rewarding work you do.

I try to encourage my teams to think beyond business titles and roles, and more about the skills they want to gain, the experiences they want to have, and what I talk about as being the next next in their career.