Singing dreams to HR teams - My Unconventional Path
- gillian1955
- Apr 23, 2024
- 7 min read

No one dreams of being in HR when they are a little kid, at least that wasn't common among us older millennials and Gen Xers. I didn't even know what HR was back then, and my small liberal arts school in upstate New York didn't offer it as a major. I'm writing this because I believe my success in HR isn't despite this lack of HR schooling. I'd argue my diverse, non-HR education and early experience equipped me even better with the skills it takes to be a successful HR leader. Many HR leaders have their versions of how they "fell into HR" and I'm sharing my story with you here. I hope you enjoy it, and more importantly, I hope you gain a piece or two of valuable insight that you can bring to your own life and career experience.
Early Influences:
I wanted to be a singer when I was little, Whitney Houston specifically. I would belt out The Bodyguard soundtrack in my bedroom with my hairbrush microphone and dream of being on a big stage one day. I did choir and participated in lots of plays and musicals. While I thought this was preparation for my solo vocal career, it was actually cultivating a stage presence and confidence that I would bring to public speaking and all-hands meetings for hundreds of people. (For those concerned, the dream of singing is not dead, but it's shifted to occasional karaoke moments performing Whitney's "I Wanna Dance with Somebody").
In school, I excelled in math, but math definitely wasn't my desired career path. There's a school of thought that pressures kids to know what they want to do early in life so that they can start taking AP classes in those subjects in high school, major in very specific areas in college, get internships every summer (and even during the school year) so that by the time they've graduated, they already have years of experience in their desired field. I do not prescribe to this school of thought. My childhood summers were spent at camp, and as I got older, I spent summers either as a camp counselor or a waitress. Reflecting on this, babysitting 13-year-old campers at an eight-week sleep-away camp, and dealing with restaurant customers unhappy with their burgers equipped me better than I could have ever imagined for a career in HR.
In college, I majored in French and International Relations - I studied in Paris and took courses in several different fields like Political Science, History, and Economics, so I could figure out what I really liked, and where I excelled. When I graduated, I got a job doing sales for a big consulting firm in Washington DC. I was a 21-year-old, calling Chief Legal Officers and General Counsels trying to sell them best practice legal research. I learned invaluable skills like how to negotiate, how to get to my point really quickly, how to speak the language of the person on the other end of the phone and really connect with them, and most importantly, how to hear "no" A LOT and keep going back for more with my head up.
I was promoted to sales manager, and for the next year and a half, I took the lowest-performing sales team and got them to be the highest-performing. My success was not because I had deep product knowledge or extensive sales experience, nor because I had read a bunch of leadership books. (My love of Patrick Lencioni, Brené Brown, and Simon Sinek would come later in life.) I got to know my team, personally and professionally, and figured out their strengths and weaknesses. When our pitch wasn't working and our numbers were down, I looked at it like a puzzle we needed to solve. We did script-editing workshops and tried a bunch of different pitches until we found what worked. They started to call our weekly 1:1's "therapy sessions" because our discussions were about struggles, challenges, and the support they needed, not just about their quotas and pipelines.
A spark was ignited in me. I realized that what I truly loved about my role was supporting and developing my team. It wasn't about the numbers or hitting quota. The fulfillment came from watching my team grow and achieve success, and seeing how my influence on them helped them get there. I was like a proud Mama Bear. And I knew I needed to take this experience into the field of HR.
The Big Pivot:
In the fall of 2008, I quit my job, moved halfway across the country, and embarked on my journey into HR. In my defense, I made the decision to do this in late Summer before the entire economy crashed, but nonetheless, one could look at this as a pretty reckless decision. It was the best decision of my career. I found an HR Internship at a small tech company, working for the VP of HR who needed help with HR operational tasks. I wrote employee handbooks, curated harassment training, ran payroll, and handled benefits. Six months in, they brought me on full-time as an HR Generalist, and I started to take on higher-level work - managing the HR system, recruiting coordination with hiring managers, and spending time building relationships with employees and leaders across the company. Three years later, the VP of HR left, and I was promoted to the HR leadership role. I was pretty sure the president of the company was nuts for promoting me then, but as a great mentor does, he saw something in me that I didn't yet see in myself.
For the next six years, I learned more than I ever could have imagined about building a team, HR vision and strategy, cultivating and nurturing company culture in a high-growth, global environment, M&A, and more. I sat at an executive table at age 27 listening to discussions of valuation and EBITDA right after the first Private Equity group invested in us. I was SO lost. I pulled our Corporate Development Manager aside after the meeting and asked him if he'd spend an hour with me and teach me what happened in that meeting "as if I were a 5-year-old." Because that's what I felt like. And his face lit up like one of those same 5-year-olds on Christmas morning. In my nine years at that company, I learned invaluable lessons about what having a mentor and advocate can do for you, and the power of asking for help.
For the last fifteen years, I've led People teams at companies of varying sizes in different industries - technology, oil and gas, sports, and real estate. Every time I join a team at a new company, I have the same approach: build relationships and uncover needs and opportunities by spending time listening and learning from people at all levels across the company; building and nurturing a People team that's mission-driven to help and support our customers - our employees. All the programs and initiatives that we implement should be in service of driving business success through cultivating an environment where people can be the best version of themselves. The details of the journey may look different depending on the company, but the goal is the same.
Key Principles for Success:
Here are a few keys I believe have been critical to my success thus far (spoiler alert! None of them require an HR degree):
Curiosity - learn how to love learning, and never stop. Learning looks different for everyone, so find what fills your cup. Look at challenges as jumbled-up puzzle pieces that you need to piece together to create a beautiful picture. And ask all the questions; you'll be surprised how many people are willing and eager to help you.
Humility - You are going to fail, probably many times. And that is a good thing - it's how we grow. We just have to be humble enough to take it all in stride, embrace it, and keep moving forward. When I fall down, I laugh at myself (literally and figuratively), and then I pick myself right back up, get back out there, learn, and try again.
Determination - I'm fiercely competitive (as my soccer teammates will tell you). My drive and determination are about bettering myself so the team can succeed. This has been such a powerful motivator in my professional life. It's not about being determined to achieve personal success, though that does come. It's about unwavering commitment to self-improvement in support of a shared goal. And it feels so good!

Fun - We get so caught up in getting good grades, fancy titles, and big salaries that we often forget we only have one life. If we can't figure out how to have fun along the way, then what are we doing? I make sure to laugh every single day, preferably with other people. It's such an amazing recipe for happiness.
Moving Forward:
In the next chapter of my career, I want to take everything I've learned and be able to help more people than I could by being part of one company. My co-founder and good friend, Gillian, has her own winding road journey that led her to this same place where we can bring our respective talents and passions together for our mission of elevating the people around us. Intrinsic People, as Gillian describes in her earlier blog "FunEmployment," stems from our shared innate qualities - empathy, integrity, and humor.
Gillian and I are excited for this new journey and all the possibilities that lie ahead of what we can accomplish, whose lives we can touch, and how many people we can elevate and influence for the better. It's also scary as hell because we've never done it before. So, we take the leap, together, and in the brilliant words of Lin-Manuel Miranda, we're "young, scrappy, and hungry, and [we're] not throwin' away [our] shot."
Keep rockin',
Casey
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