Cierra Olson, Head of People on Influential Women

Influential Woman · Tech

Cierra Olson

Head of People, DOOR

Lake Saint Louis, MO

Certifications · Degrees · Memberships

Degree Degree in Education from Lindenwood University

Her Story

About Cierra

I've been working in startups for about 10 years, starting in biotech and moving through health tech, though I'm currently in straight tech at a publicly traded company. I'm a builder - my career has always been about picking a company and building scalable infrastructure built on automations, AI, and really strong culture-driven policies from the bottom up. At my level, I focus on three main areas: executive business partnering, operations and organizational development strategy, and operational efficiency. My most notable achievement was at Velsara, where I was employee 25 and grew that company to over 300 employees globally in just about 4 years. I also managed the M&A of 3 companies across 17 countries into one space, all while in my third trimester of pregnancy with another little one at home. My background is unconventional - I have a degree in education from Lindenwood University and was actually an opera singer and choir teacher before entering this field. I started at a startup as an office manager and quickly became the HR manager, teaching myself the HR side and taking over things that nobody was doing. The rest is kind of history. My favorite part of my job is that I'm very much who I am, which allows people to come talk to me and tell me what's going wrong in the business so I can advocate with the executive team and remediate and fix it before it's critical mass.

Her Interview

Ten minutes with Cierra

01What do you attribute your success to?

I attribute my success to my family. I know that sounds corny, but you're talking to a girl who wanted to be an opera singer and turned around and was able to build a career into an executive HR position. I remember when I decided to stop doing music, I remember crying to my husband and my grandmother and saying, the only thing I know how to do besides this is bartend. And both of them kind of smacked me over the head and said, you're too smart for that. You can do whatever it is that you think you can do. And lo and behold, they were right.

02What’s the best career advice you’ve ever received?

The best career advice I ever received was actually from a college professor, and I'm glad I got it early because for those of us that are really driven and high achievers, when we get criticism, we beat ourselves over the head with it. But a lot of times, I was told, it sounds like you're clapping back at the criticism, but really, you're mad at yourself, and you immediately fix the behavior. But perception is reality. If somebody thinks that you're not taking their feedback, that paints you in a really negative light. So I'm very glad I got that early, because that can be hugely detrimental to somebody seeing you as somebody that can get promoted and can take on more, if you can't take feedback and learn from it.

03What advice would you give to young women entering your industry?

The advice I would give to young women is believe in yourself, which, again, sounds corny, but just because something isn't on your resume doesn't mean you cannot do it. The most transferable job skill is to be a lifelong learner. Figure it out. Do it yourself. Believe that you can do it. Having that versatility will get you so many places, and honestly, no matter what job you enter the field in, if you have versatility, you can go almost anywhere with it. And the other thing is, which I know we say to women all the time, but don't be afraid to speak up. Stand in a room, hold your space. Make sure you're making space for others, but don't be afraid to stand up and deliver space in the room. I think oftentimes women apologize for existing, you know, the I'm sorry syndrome constantly. I'm guilty of it as well. Don't apologize for existing in a room.

04What are the biggest challenges or opportunities in your field right now?

I think right now, the biggest struggle is that we are in a really transitional time with our workforce, both from the intergenerational standpoint. You know, at my company, we have Gen X all the way down to young millennials, and they want something different, and they all believe that how you get to that product is different. So we've got that difference in workforce, but also the AI forward versus the non-AI forward group. And so when you're trying to get a job or trying to build a team, you have to really look at it and say, okay, what is existing right now, or what is the environment I'm trying to get into, and what do I need to keep in mind? How do I need to position myself or my team for success?

05What values are most important to you in your work and personal life?

I think the things that are really important are clarity - and I just mean clear as kind, I mean telling somebody, this is what I need from you, this is how you're gonna own this, this is what I'm gonna own. I think ownership - clarity leads to clear ownership, which is a lot of reasons things don't get over the line. I also think time to impact. I cannot stand when we sit around and we talk about something, talk about something, talk about something, but it never gets put into action. So, time to impact is a huge one for me, and what you're doing needs to have that impact. And then that next one, you know, this is a little corny, but remembering that people are people, and not their job description. I think that is what's made me the most successful, is I build trust by just - I'm very on the - I'm who I am, and it allows people to come talk to me and tell me what's going wrong in the business, so I can advocate with the executive team and remediate and fix it before it's critical mass.

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