Reini Chipman - Chief People Officer @ Simple

Reini Chipman is the Chief People Officer at Simple, an online banking/tech company in Portland, Oregon that was built on “genuine human goodness” and helps people save their money. She’s an engaging and insightful person who I’ve know for long enough to realize that she’s a powerful force in this world. I’m impressed with her genuine commitment to challenging and disrupting the status quo through making her company an inclusive and truly supportive environment. 

I asked Reini a couple of questions below and learned that her job is part Human Resources and part Social Work/Life Coach/Game Changer - disrupting the banking industry and HR at the same time.

Is this what you were planning on doing with your career?

In college I studied Psychology and Social Work and always envisioned helping, supporting, and being involved with people. Like many HR folks, HR sort of fell into my lap. My school didn't offer a formal path to study HR. I kind of stumbled upon it, and then I noticed that it’s interesting and complex, and every organization has some form of it. 

Until about 4 years ago, I didn't see myself as a C-Level Executive - and I certainly didn’t see myself working at a bank. But Simple is a tech company that is changing the way people bank and think about their money. We’re here to help people feel confident with their money, and I think that’s good for the world. I’ve always wanted to do good in the world and help people, and at Simple I get to do both. 

If I had the luxury and the privilege of going back to school and studying formerly again, I would probably study anthropology. 

How did you end up with this job and what were some of the challenges in your career?

Coming out of school, I had learned how to be a social worker and how to work within the non-profit and social services world. I took a position with a non-profit organization that was focused on helping women access training to find employment. Unfortunately I think a lot of non-profit organizations aren’t very effective at bringing about real change. And after several months of being part of this organization I started to realize that I was actually enabling and perpetuating oppressive institutionalized frameworks and systems. I was concerned that we were unintentionally doing harm. 

I had a candid conversation with myself and decided that real change starts with me and with my own community. Lots of folks have written inspiring words about “being the change you want to see in the world” and I am a big believer in that perspective. I’ve noticed the most powerful and sustained change happens when we build on the strengths of a community. And if we aren’t an active member of the community we’re trying to empower, how can we possibly be effective as change agents?

So I said, "Well who are my people?" I grew up with a mix of blue and white collar dynamics, so I decided to check out the for-profit world. I found a job in recruiting, and started helping people find jobs. I moved away from helping people in communities that I wasn’t actively a part of to helping people in communities where I better understood the strengths and possibilities. That’s when I found the practice of HR, it was through Recruiting. I loved recruiting because on many days, I felt like a job fairy! I mean, who wouldn’t want to tell someone “You got the job!” My first recruiting gig was in the healthcare industry and it was awesome learning, but I also learned that at my core I'm not aligned with much of the healthcare system in the US -- I am more interested in holistic ways of approaching wellness over traditional practices. 

I searched around and found a new entry level gig at a tech company doing recruiting. It was in this job that I started understanding the depth of what it means to be with people on their employment journey - the depth of recruiting and the depth of HR. I got really hooked. 

I've been intrigued by technology from an early age (even though I studied mostly social sciences, I'm decent at math!). I have a secret engineering/technical side to me - I love innovation and iteration and continuous improvement. The methodologies that engineers use such as agile have really come into focus and I see the agile methods extending beyond just engineering. Other departments such as finance and HR have taken a much more iterative approach to how they help build the business. I keep coming back to tech because this is where there's the most readiness for revolutionary thinking and acting around what it means to be at work.

Why is working at Simple your dream job?

Simple’s purpose aligns with my purpose. I've done a lot of personal work in the last couple years to get clear on what my purpose is and why I exist on this earth. I'm pretty clear now that I'm here on this earth to help people feel freer so that they can live their best life. And work (paid and unpaid) is a huge component of our overall wellbeing. I want to help people to feel free to live the life they want to live, to laugh and to love. And careers are a huge gateway to get there for most of us. So being part of Simple’s people team is a natural fit for me because we have the privilege of helping to build the organization in a way that empowers everyone to feel confident and to have epic experiences at work.

Simple’s values align with my values. My biggest personal value is gratitude - the opposite of which I describe as entitlement. A dark side of being in any given community can be the unintended impact of institutionalized oppression. Every institution has unconscious bias and institutionalized oppression and I know I participate in it every day. Because of my privilege, I’m inherently part of the problem. What is different about Simple is that every person that I meet here is curious and empathetic, in service of trying to understand what someone's superpowers are, their craft, and just who they are as a human. It’s a magical place because there's a critical mass of people who want to build a truly diverse and inclusive work environment. And, we know that is not a static thing where one day we get to say “hooray - we’re inclusive!”. We acknowledge this work won’t be done in our lifetime. But I've never been surrounded by a group like this of 300, or even 100 people who pretty much all feel that way. We do the hard right things and have the big conversations -- even though most of us aren’t quite sure how to do it and we’re scared that we might get it wrong. 

All this said, I strive to practice abundance thinking over scarcity mindset. So I’m confident there are lots of dream jobs out there for me and for all of us. And...I’m deeply grateful that I’ve found one because there’s nothing quite like doing work that we love.

What advice would you give someone who is trying to find their dream job?

Take good care of yourself. It might sound counter-intuitive to prioritize self care, but it’s one of the most important ongoing conversations that I have with myself. I know that when I take good care of myself I’m more likely to be present and in the moment.  This sets me up to be more likely to notice an opportunity or have a conversation with somebody that can lead to that next cool thing. Also when I’m feeling healthy, I’m more resilient during times of failure. 

We all have these moments in life when things pull us away from our self-care commitments. It’s okay to lose focus on self-care for a moment but ultimately finding and keeping a dream job is an energy game, and we need to remember to keep putting our own oxygen masks on first.

How do I do it? I try to remind myself to own my well-being and be deliciously selfish and indulgent. I’ll say to myself “wow, I have a lot to do, but I’m going to take a bath because I need some quiet time.” or “I’m going to have a dance party with my son because I’m craving connection with him and everything else can just wait.”  

I certainly don’t nail it every day but I know that everything is better when I prioritize self-care.