A Career Story: On Compassion and the Almosts That Shape Us
Hi, I’m Courtney Branson, one of the founders of EverMore — the performance glow-up. We’re big on reflection, storytelling, and conversation as the key bits of developing talent instead of reviews. As part of this mission, I want to share career stories, with no better place to start than with my own.
Tell us about yourself.
Gemini ☀️ Leo 🌙 Virgo ⬆️
I’m a prolific diarist, bruised idealist, and someone who’s always trying to leave people and places better than I found them.
I love innovating in employee experience, and I’ve spent 17-ish years in tech companies, big and small, crafting award-winning cultures.
I live in Austin with my husband, daughter, and four rescue pets. I love to hula hoop + roller-skate, and I’m forever working on letting go of perfect.
Here is my career story.
What career did you want as a child?
Fashion writer in NYC.
I spent hours in my room acting out Courtney’s Closet, my make-believe fashion show. I’d piece together k-mart clothing and hand-me-downs before strutting in front of my mirror. In the late ’90s, I even got Teen Digital Diva, so I could design my own fashion mag.
This was a quiet dream that felt silly to share as a child. But in retrospect, it set the stage for a lot of who I am today — scrappy, sustainable, and really alive when I’m creating/writing.
What were the circumstances you grew up in, and how did they shape your view of work?
I grew up lower-class in an upper-class town as the eldest of four daughters. We were acutely aware of money and how finite it was.
My dad gave everything to his job to ensure we were better off than he was. He touted mantras like “if you work hard, you’ll be rewarded.” I believed in meritocracy and fairness. Schools validated that with grades and honors.
I was ill-prepared for the realities of work. It was the first time my contributions didn’t speak for themselves, and the rules of the game weren’t clearly stated. I had to get good at reading people, understanding the politics, and then convincing others to address the unspoken norms.
(One day, I’ll tell you about the paradox of being indoctrinated in religion, only to end up leading culture at work.)
What did your first job teach you?
My first job that wasn’t babysitting was at Sun & Ski Sports in Grapevine Mills Mall. I was in high school, so it taught me the obvious bits of balance and humility. (The uniform was 🤮)
Most importantly, it kick-started my journey to shed my shyness. Whether at the front door, cash wrap, or sales floor — it was my job to talk to strangers. With each “hello,” I came more and more into my own.
I’m oddly grateful for that job.
What was your experience entering the workforce?
The title of that chapter would have been — Take what you can get.
I entered the workforce in 2008 with a liberal arts degree. My family had no connections or network. They gave me a place to live and my dad’s resume from 1982 for inspiration. I would sit at the public library all day applying to jobs. The few interviews I got were embarrassing; one was 100% a scam that I drove an hour each way to figure out.
The great recession left my options at minimum wage as I watched my friends, newly minted business grads, flourish. At 23, I felt profoundly behind. And no one tells you how lonely that can feel when your life hasn’t caught up to your high-achievement identity.
I had to accept that I was moving at my own timing. It also challenged me to find meaning in what otherwise looked like dead-end jobs.
We’re all asked, “What do you want to be when you grow up?” Rarely are we asked, “Who do you want to become?”
At that point, I felt the only thing in my control was how I showed up, so I spent a lot of time on who I wanted to be.
What’s your villain origin story?
Firstly, can I call out abercrombie for firing me from my college part-time job because I needed someone to take my shift when my grandfather died? I’m haunted by the glee in the store manager’s voice when she told me.
But, I digress. My villain arc happened in 2009. It was my first performance review, and I received a 3% salary increase out of a possible 4%.
I pried until my manager revealed a seedy underbelly — the leadership team lowered my ratings to balance out the team. I was seen as docile. (The sexism and ageism were so blatant even my 23-year-old brain clocked it.)
I kept pushing back until I got the full increase, giving me an extra $0.15 per hour. 🫠
Following this, HR put me in remedial sensitivity training for being “difficult.” I could not fathom why the people who were supposed to help were doing this. I could’ve gagged if they said “that’s just the way it is” one more time.
Out of spite, I pivoted my career to HR because I believed I could do it better. I’ve tried to keep that promise and be the advocate that I wish I had.
What was your first big career break, and how did it happen?
Joining Match Group in 2010 was my break — one that I did not squander.
I wanted to do HR at a “cool” company that let me wear whatever I wanted. So, I created a vision board of workplaces that fit the vibe in Dallas, which was basically Match Group. For over six months, I stalked their career board until a receptionist role opened.
I couldn’t believe I got the interview, much less the job. It was $35,000 a year reporting to the new VP of HR. Two weeks into the job, the HR Manager resigned, and I was asked to help in a bigger capacity. They hired a temp for reception, and I never went back.
The VP of HR truly believed in me. When I think about being 25 — creating the culture club, pitching social responsibility programs, starting an employer brand, planning over-the-top events, it’s hard to wrap my brain around it. I am endlessly thankful for that trust.
When did your career path shift — planned or unplanned?
Moving to Austin for my husband’s job allowed the current chapter of my life to begin. Match Group was my “dream job,” but I was stagnating in a tenure-based system, so I needed to leave to grow. Physical separation made that decision easier.
I see Austin as my invisible string.
Since I was a teen, folks would suggest it as a place for me. Once I finally got here, I joined the startup community, met my closest friends, decided to be a mom, and unleashed all the oddities I stuffed down in Dallas.
Is there a career moment of joy, pride, or surprise that stands out most?
So many. Being a head of people, you get to influence the things that can truly change someone’s life. It never gets old hearing stories from folks who benefitted from something I advocated for, like automatic raises, adoption leave, gender-affirming care, and more.
One thing I created, Learn Anything, was a $3k / year carte blanche to learn anything. It was formative for individuals and the culture of growth.
That program got Square Root on PEOPLE magazine’s 50 Companies Who Care list. It was a full-circle moment. I grew up reading those magazines at my grandmother’s house on Saturdays. It’s where I built my love of fashion, celeb culture, and crosswords. It felt like my past meeting my present.
Who or what has influenced your career story the most?
I’m an amalgam of so many co-workers who left imprints big and small on me. The way I stay calm in chaos goes back to a mentor in 2010. Keeping my boundaries came from team feedback in 2017. My use of whilst evolved through multiple Aussie colleagues.
These bits and pieces come together to shape you. I try not to stay in places too long if I don’t connect with the people. They’ll shape me either way.
But the person who’s been there for every year of my career is my husband. He’s proofread emails, set up events, tracked down supplies, and championed everything I do. He’s always believed in my creativity and encourages me to leave places that don’t use it. It’s a safety net.
What values have remained constant for you through different stages?
Compassion. Whether I was 16, telling someone their card was declined, or today letting someone go, it takes the same balance of honesty and dignity.
Being in people + culture isn’t life-saving, but I do encounter folks in some of their worst moments — being let go, bereavement, break-ups, betrayals. My words and support can either add shame or soften the blow. Compassion lets me find meaning in the work.
Did you ever feel pressure to conform to someone else’s definition of success?
1000%. I grew up with a set of ideals from a conservative, religious, Southern family. I was expected to be “good” in every way — good grades, good manners, good discipline. My main exposure as a kid to other ways of being was MTV’s The Real World.
In college, I got to redefine my belief system, but I still had this pull to be “good.” It was like etched inside of me, so I handed over my time, energy, and soul to companies, feeling lucky for scraps until I burned out.
I started to question if the money and praise were worth it, which meant grappling with my fear of financial instability. I also felt like I was letting down the generations before me by not pushing myself as far as I could.
At the same time, the evolution of social media masterminded this wave of comparison, so I felt perpetually behind again — almost like I couldn’t escape being a late bloomer.
So much of my 30s was reckoning with who I’d been molded to be, and turning inward to figure out what actually felt authentic to me. That came with letting go different versions of myself that did or could have existed.
I’m still examining the role society, childhood, and history have played in shaping who I am — constantly reflecting on who I’m becoming.
How do you define success for yourself today?
It’s mostly running through a gauntlet of questions:
- Am I in my values? Would those closest to me recognize how I show up?
- Am I doing the best work of my career? Am I learning new things?
- Is my family joyful and connected? Do I have time for my friends? Have I danced in the kitchen today? Can I romanticize my life?
What skills or mindsets helped you grow the most in your career
- Adaptability — willingness to hear someone out, change my mind, or learn something new. It helped folks want to work with and for me.
- Being Weird — confidence to say the whimsical, half-baked idea or share the messy draft. I learned to trust the process of riffing and iterating. I’m forever surprised by how many wacky ideas got greenlit. It’s why EverMore has a riff, don’t reject value.
- Intentionality — consideration of what’s best and possible in a circumstance, especially for any decision that impacts people.
Was there a moment when you felt like giving up or changing direction entirely?
I almost didn’t return from maternity leave. My salary barely covered daycare costs, and my baby was so cute, it was hard to justify going back.
I’m so glad I did. Motherhood changed me profoundly, and so did becoming a first-time manager — both happened at the same time. That overlap sent me on an epic journey of growth, and now motherhood and management feel inextricably tied together.
If I separate them, I fear I lose all the lessons: How to nurture someone’s potential without projecting yourself onto them. How to apologize. How to be a safe place for someone to admit a mistake. How to see — and hold — the contradictions in other people.
It’s easy to reflect on all the times we walk away from something, but sometimes it’s the almosts — the times we don’t walk away that end up shaping everything.
This was one of those almosts. And I hadn’t really thought of it that way until this question.
What were the biggest obstacles you faced in your career journey?
In so many ways, I fit the mold of naivety or femininity, so there’s an expectation that I be demure and deferential, but I have a bite to me that surprises people. So, societal expectations have worked for and against me.
The appearance factor mixed with assumptions about HR gives me an uphill climb in building credibility everywhere I go, but I just view it as a challenge to win people over.
What have been your biggest failures?
That list is just all the things I haven’t done. I’ve never regretted speaking up, saying an idea, or trying something new, even when it didn’t work.
If your career story were a book or movie, what title would you choose?
The Vision Board
I make them. I love them. I collage them.
What’s your favorite quote?
Don’t sell your soul to get anywhere
because you may need it one day.
I think quotes find us at a time and place. This one found me recently during a Project Runway rewatch from season one finalist, Kara Saun.
What books are canon for you?
The books I always return to are…
- Le Petit Prince — for a dose of whimsy and wonder
- Crucial Conversations — for when I need to say something hard
- Orbiting the Giant Hairball — for a quirky, authentic take on culture
- The Westing Game — for a taste of nostalgia and connection to the past
What are you listening to right now?
I’m forever listening to My Morning Jacket, Pete Yorn, and Mazzy Star. They’ve carried me through so many years that even the sad songs feel like a warm blanket.
But, right now, it’s The Summer I Turned Pretty Season 3 soundtrack, mainly because Bizarre Love Triangle by New Order was iconic (iykyk).
What’s your pet peeve?
Being asked to react to or decide something on the spot. (I need to mull!)
What’s your current passion project?
I’m writing a series of horror short stories inspired by my time in startups. It’s been cathartic to reimagine colleagues (and myself) as villains, heroes, and everything in between.
And, I’m building EverMore. 👇
EverMore helps you with regular reflections, coaching, and keeping track of your wins, learnings, and feedback over time (plus, you own it + take it wherever you go!). Join the waitlist to have early access to our beta 👀
