A Career Story: Kelsey Peterson On Authenticity and All That's Left to Learn
- Courtney Branson
- Oct 27
- 10 min read
Welcome to our series on career stories. EverMore believes reflection and storytelling are key to personal and professional growth. Meet our Cofounder + COO, Kelsey Peterson.
Tell us about yourself.
Hi, I’m Kelsey—professionally, I’m an entrepreneur and a People + Culture leader at tech startups. I enjoy creating and building things that support the future of work.
Right now, this is being put into EverMore, a reflection tool that I a) get to build with two of my favorite people, and b) truly believe will help people understand themselves + where they want to go next.
Personally, I’ve been writing songs since I was ~6 years old. What initially started as me processing my life experiences alone in my bedroom has turned into meeting other incredible musicians, getting to play my songs in front of others (sometimes with people knowing the words!), and a few years ago, starting a business around creative collaboration.
What career did you want as a child?
Musician and later on, a songwriter. I watched Coyote Ugly at ~11 years old and realized this was a job in the music industry.
When I decided to go to college, I initially studied music education, but later switched to music business with an emphasis on non-profit (like opera, orchestra, ballet).
I always knew music was going to be my longest relationship, and even though I don’t do it professionally, I’m grateful it’s what I do for the love of it.
What were the circumstances you grew up in, and how did they shape your view of work?
While we lived in a fairly wealthy suburb north of Chicago, we went through our own troubles as a family, often with my mom being the consistent sole provider. She would work late, pick up food on the way home, and I was often the older sibling who made sure everyone else was fed and safe until she got home.
While this was at times difficult, I also saw how committed and passionate my parents were at their jobs. My mom worked as a dietitian at a hospital for 20+ years before moving into home infusion—she spoke of helping both humans (elderly, those out of surgery) as well as veterinary clinics to help people’s pets. My dad was initially a painter + artist, but later went to Law School to practice workers' compensation. He always cared for people (and still does), sharing stories of companies putting people in risky situations.
What’s your career villain origin story?
Earlier in my career, I worked at a tech startup and was so thrilled when I finally could have colorful, pink + purple hair that I longed for—finally feeling like my outer identity matched my inner self. To set the stage: I have really dark hair with red undertones, so the process to bleach + color my hair was exhausting.
I was preparing to relocate with this startup to the Bay Area, bringing our culture to a company we had recently acquired. I signed my lease, coordinated my move, and was a few weeks out when this company “reminded” me of a deal I had agreed to (which I didn’t) to change my hair color to a “normal” color (which I eventually decided to do instead of risk my employment and move).
While working in the Bay Area, it became even more upsetting when I would meet with possible customers (a new role expectation) alongside a sales leader, who consistently remarked, “Kelsey used to have the coolest hair color. Why did you change it?” After so many times, I started coming up with different answers, hoping he would notice the inconsistency (he didn’t).
I left this company within a year, deciding I would make it my mission to never let anyone control how I express myself and help others do the same. This experience prompted me to move into People + Culture, first as a recruiter, then as a leader.
I would make it my mission to never let anyone control how I express myself and help others do the same.
When you think back to your very first job, what did it teach you about yourself?
I joined the workforce shortly after the recession (in 2010). My first job was as an unpaid intern at a prestigious opera company. It was my dream job out of college after studying Music Business, and I felt so grateful to have gotten my foot in the door.
It took a while to get the Assistant role (the next step up), working within fundraising and events, but I was so excited when I did. I learned a lot about working with donors, especially those at the highest tier, planning large (and small) scale events, and I met others who were passionate about opera + classical music.
There were challenges, and the pay was atrocious (I can’t bring myself to share, it’s that bad!), plus the very late nights running from an event to the train back home (where I lived with my mom) were exhausting. I can still feel the level of exhaustion, sometimes to tears, even as I write this out.
One thing that experience taught me — in a very roundabout way — is that it’s okay to make mistakes. Back then, I was penalized and shamed for them, especially as an intern and assistant. It’s incredible that I’m still unlearning that 13 years later, but I’ve finally come to understand that mistakes are part of growth.
Looking back, what was your first big career break, and how did it happen?
At any time, your career and life can shift and evolve for the better.
While I used to say moving from non-profit to a tech startup was my “big career break,” I think I’ve actually had far more in the last 10 years of my career—becoming an entrepreneur with another cofounder + friend, getting into several accelerators and pitching to investors for the first time, landing an opportunity to move into recruiting + people operations by my now cofounder + friend, and eventually growing into a Director of People working alongside leadership.
They all feel like equally big career moments, so it constantly reminds me that at any time, your career and life can shift and evolve for the better. Take each opportunity that’s provided.
Who or what has influenced your career story the most?
Courtney Branson
My mentor, friend, and now, cofounder, who took me under her wing when I moved into People + Culture.
Taught me what a great manager looks like and supported me through both promotions and personal challenges.
Helped me unlearn early career conditioning that mistakes = punishment, showing instead that mistakes are opportunities to ask for help and grow.
Opened my eyes to the possibilities of leadership and shaped the kind of manager I strive to be.
Mary Walker + Daydreamer App
Cofounding Daydreamer with Mary after moving to Austin was a huge influence. I wanted to pursue music after ~7–10 years in tech/corporate.
We shared the challenge of not knowing local musicians/artists, and built a geolocation app to connect creatives outside of Instagram.
Learned startup skills hands-on: pitching investors, building community, managing beta users, hosting events, running an app.
The experience was arduous, chaotic, fun, exhilarating—and it ultimately led me into People + Culture.
What skills or mindsets helped you grow the most in your career?
Growth Mindset
No matter what you think you know right now, there’s always so much more to learn. Even as changes or challenges occur, it’s important for me to stay curious, open, and humble in every stage of my career. Having a growth mindset has often allowed me to treat every role or experience as a chance to expand and learn more about myself.
Adaptability
I see the world as ever-changing and fluid—no one person is one thing forever, and that’s a really good thing. I find it really important to move through changes and challenges with openness, flexibility.
Across my life (not just at work), I’ve known the feeling of holding onto something, not letting it (or myself) change, and being a source of tension. However, I have gotten much better at understanding that things happen for a reason, that it’s better to go with it than force it to be any which way.
Reflection
If there’s anything that’s helped me the most in my career (as well as my personal relationships + life), it’s reflecting on a regular cycle. I really enjoy cycles, particularly monthly, quarterly, biannually, and annually. I don’t wait to reflect only when something great or bad happens. I focus on doing it regularly, so it’s a strong muscle and habit that feels exciting to do.
I see the world as ever-changing and fluid—no one person is one thing forever, and that’s a really good thing.
Can you describe a moment when your career path shifted—planned or unplanned?
While struggling to get investment at Daydreamer, I looked for a full-time job and applied for a Customer Success role at a startup—I didn’t get it. That rejection led to Courtney reaching out with openings on her team, including a ranking survey that made me realize how much I enjoyed the idea of People, Culture, HR, and recruiting.
We then had this honest, real follow-up conversation, with Courtney asking me, “Do you want to work in HR and recruiting?” I thought the same thing, and it was in that moment when everything earlier in my career clicked—how I was involved in company culture projects (like team off-sites, events, and interviewing new employees) and could leverage my deep experience as an employee to make sure it was better for others.
What started as an unplanned pivot turned into the clear path forward that launched my People + Culture career.
Was there a moment when you felt like giving up or changing direction entirely?
Have you seen my LinkedIn? I’m definitely the type to change direction entirely. People in the music community often say they don’t understand my career path when they find my LinkedIn profile or learn about what I do professionally.
Journey so far: nonprofit arts → billing/renewals in SaaS → training customers on financial software → record store → built an app → People & Culture → now founding EverMore.
Growth mindset shows up here: “I now know X, now I need more information about something completely different.” Every pivot has helped me learn something more about myself, and I really enjoy being a generalist turned specialist throughout my career.
What have been your biggest failures?
I actually don’t look at my career as having any failures—instead, I see these as pivots or moments where I outgrew a role or an environment. However, if I were to list a few:
Deciding to move on from DayDreamer, the startup I previously cofounded. We were trying to raise investment, not seeing the traction we expected, and I had this intuitive feeling that I needed to move on. It was a very painful and difficult decision, but ultimately one that was for the best.
All the times I didn’t trust my gut and intuition, which ultimately led me to play it “safe” when implementing a new process or project. From the HR role, I think this is actually what gets archaic people processes (like performance reviews, 1:1s, career goals + development) to remain in our everyday systems. We play it safe and don’t take the necessary time to wonder, “What are we really trying to do with this? How could this be carried out differently to help people?”
I actually don’t look at my career as having any failures—instead, I see these as pivots or moments where I outgrew a role or an environment.
What values have remained constant for you through different jobs or stages?
Curiosity – Since childhood, I’ve always asked why and how something works. I love going deep into subjects I’m excited about and believe life should be guided by curiosity.
Authenticity – Expressing myself as I am, whether that was Minnie Mouse leggings as a kid or crying in a meeting as an adult. Not hiding emotions creates safety for others to be human, too.
Integrity – I strive to be honest, transparent, and true to my word. It’s hard for me to lie or hold back, though in People + Culture I sometimes must (e.g., layoffs). Integrity shows up in being clear and thoughtful with others, even in small ways, like rescheduling with a friend honestly. It’s both a strength and a challenge, but always rooted in doing the right thing.
Did you ever feel pressure to conform to someone else’s definition of success?
I grew up with parents who valued stability and long-term jobs (15–20 years at one company). Early in my career, I felt pressure to stay longer in roles and pursue traditional success because “that’s how it’s always been done” before. This initially equated success with titles, money, and working at flashy, well-known companies.
How do you define success for yourself today?
Throughout my now 15+ year career, I’ve learned that chasing titles and intensity left me unfulfilled—my version of success looks very different now. I seek—having value, impact, and questioning how something can be done better. If I can help other employees and managers be their best selves at work, I’ll know I’m successful.
Ultimately, it’s important for me to be fulfilled and confident that I’m making change happen in the community around me.
What are your favorite quotes?
“We accept the love we think we deserve”—The Perks of Being a Wallflower
“It’s never a good time to take vacation, so it’s always a good time to take vacation”—my friend Chris (dungeon master)
“If you don't like something, change it. If you can't change it, change your attitude”—Maya Angelou
What books are canon for you?
Big Magic – Elizabeth Gilbert (my bible)
Radical Candor – Kim Scott
Give and Take – Adam Grant
Start With Why – Simon Sinek
The Tao of Pooh – Benjamin Hoff
The Art of the Turnaround — Michael Kaiser
What are you listening to right now?
Music—every 1-2 years, around my birthday, I make myself a new playlist and add songs over the course of the next year. So, right now, I’m listening to my “38” playlist (here). This includes some of my favorite artists, like: Misterwives, Orla Garland, Hayley Williams, Improvement Movement, and The Marias
Podcasts
Call Her Daddy with Alex Cooper
Good Hang with Amy Poehler
Ologies with Allie Ward
Reimagining Love with Alexandra Solomon
20VC with Harry Stebbings
What’s your pet peeve?
When someone can’t take responsibility for their actions/words and say “I’m sorry” or “I was wrong.”
If they can’t, I end up going to very creative lengths to get someone to see their part in conflict or disagreement, sometimes going so far as to tell them, “You did this, can you please say sorry?"
What’s your current passion project?
I would say gardening right now. I’m also preparing my house to sell, so there’s a lot of landscaping I have to do, as well as internal touches. If anyone has any staging advice, I would love to hear it!
Where can we follow you?
You can follow me on LinkedIn
as well as my music Instagram
Kelsey Peterson is a cofounder of EverMore, which is reimagining performance management, growing planning, and career reflections for the future of work. She's a 2x founder, former People + Culture leader for mission-driven startups, and a singer-songwriter.
