Unraveling the Illusion of Prestige
The powerful story of Felisha Wirtshafter: Finding prosperity in perseverance
🔖Welcome to Misplaced Musing! I’m — an unconventional leader in tech curious to explore damaging stereotypes that can ultimately prioritize ego over humans.
This week’s Misplaced Spotlight 🔦 features Felisha Wirtshafter, a proven trailblazer defining the landscape of high-quality customer experiences within some of the most competitive sectors in the technology industry.
Diving into her origin story below has completely reshaped my professional perspective on Felisha. The adeptness and gracefulness I've witnessed in her were forged, unbeknownst to me, through fundamental adversity from humble origins—adversity that didn't embitter her, but rather, sculpted her into a tenacious, empathetic leader.
Throughout her words, we're inspired by how motivated she stayed anchoring her pursuit in dreams that others may have dismissed as fantasies. If you know Felisha, this optimism permeates her very essence. It's incredibly fulfilling to understand its origins.
’s Story 🔦
Being in Customer Experience wasn’t part of my game plan.
One of the aspects I love most about a career in CX is that no one went to school for this. We all somehow stumbled into this world, and our backgrounds are incredibly diverse. Given that there are no blueprints for this career path, and very few veterans in the field, learning the ropes requires a lot of trial and error.
Early in my career, I was often the only woman in the room. I've also moved around to different industries that were completely foreign to me. I’m no stranger to the dreaded “imposter syndrome,” but that never stopped me from raising my hand to sign up for challenging projects or ask questions. I was (and still am) just so eager to learn.
I grew up in the middle of nowhere in southern Virginia, in a single-parent low-income home. We rarely had groceries, much less a college fund in place for me. When I was 13, I visited NYC for the first time. It blew my mind — I knew I had to find some way to get there. It was just so different from my small hometown, and I loved the chaos of it all. I was inspired by the people, the energy, and the possibilities it had to offer.
Growing up, I always loved art, and I dreamed of being a designer. From what I knew about NYC (which was very little!), I thought that it could be my ticket to move there.
So, I went to school for Advertising, with a focus on Art Direction. I won some fun awards for my work, interned at really great ad agencies, and worked at a branding studio.
I was still in Virginia, and while I felt like I had a real chance at continuing on my Art Direction path there... I couldn’t let go of the dream of moving to NYC.
After I graduated, I applied to a ton of different opportunities. Most were in advertising, but some were just at companies I admired. One of them being Squarespace… but, it was in the Customer Experience department.
I thought if I took this job in CX, it could be my stepping stone to something else. However, it became my island. Put simply: I found my calling.
I remember my friends telling me I was ridiculous for giving up design and working in CX instead. But, I didn’t care.
Accepting this position meant I could move to NYC, secure a salary, healthcare, and the best part… FREE lunch! I packed up my bags and moved to NYC with just a few hundred dollars in my bank account. I found a roommate on Craigslist, and my bedroom was technically a living room... but it didn’t matter, I was going to NYC.
Squarespace was considered a “startup” when I joined, but it really was (and is today) a well-oiled machine. They crush it at what they do. I am so grateful I got my start in CX there, as it really gave me the foundations of what a customer experience department should look like. I quickly grew from CX agent to their quality assurance team — where I evaluated CX agents' interactions with customers and coached them on how to create a better CX. I became obsessed with quality after that.
A few years into working at Squarespace, I got a dog. His Instagram was gaining popularity, and a company building a dog-walking app reached out to me to lead their CX team. Yes — my dog got me a job.
This was my first step into startups and my first role where I couldn’t hide in the numbers of a larger company. I was the 5th employee to join the team and quickly learned — I was crucial to making the company run. I was invited to join leadership meetings that happened to be all male and my initial reaction was to take notes vs. engage. After a few meetings, my boss pulled me aside to say "you're invited because we want your opinions, not to take notes." That was a huge changing point for me as a woman in the workplace, and I still think of this moment to this day! From there on I'd raise my hand for anything. I created and owned the entire customer journey and experience, designed our walker and customer education and onboarding, hired and managed my first team, navigated wildly emotional situations with customers (pet owners are strange, I am one!), wrote birthday cards for dogs—you name it. I caught the startup bug. I wanted to be part of everything in building a company. I loved the action, the speed at which we moved, and the ability to own and provide amazing customer experiences.
A few years later, I landed a role at Gorillas—the fastest-growing startup of all time in Europe. They were delivering groceries in less than 10 minutes, and I joined as their Head of CX for the US launch.
My time at Gorillas was like being at a startup on steroids. This was fresh off a $1 Billion-dollar round of funding and I was surrounded by incredible colleagues from some of the best companies in the world. I loved building out CX there and finding creative ways to wow our customers (and not just by showing up at their door within 10 minutes of ordering groceries!)
When our US team was laid off, a past colleague reached out to me about working at OpenSea. At the time, OpenSea was experiencing unheard-of growt— with over $14 billion in transactions in 2021 and over 1 million users. It was a really wild (and fun!) time. They weren’t hiring for a CX Director, but after chatting with the Head of Special Projects a few times– they created a role for me, which I’ll forever be grateful for.
I was hired to build out their team and develop what CX even meant in a world of web3 (which had never been done before!).
On my first day, I jumped right into hiring. A few months in, we had hundreds of agents answering tickets— I then continued on to build out an internal team of 20+ folks between customer experience, knowledge management, quality assurance, and data/analytics.
At OpenSea, I think I’ve really been able to find my superpower. I struggled a lot in school— I simply just learned differently. Growing up, I was beyond embarrassed by this. However, today, I thrive on breaking down incredibly difficult concepts and making them so easy, anyone can understand. Building simple messaging, un-complicating customer journeys, creating dynamic training experiences— it’s my zone of genius.
Personally, I never thought I’d get so lucky. I get to be in the same room as folks who’ve spent 10+ years at FAANG companies and led massive departments— really impressive folks. After all of this, I still let the dreaded imposter syndrome creep in some days— but I pride myself on my grit. I may not have the pedigree but I’m tenacious, and I’ll always figure it out.
I'm really proud of my journey. I'm glad I took a chance and I’m grateful Squarespace offered this poor girl from Virginia free lunch. Maybe I'll still pursue my dreams of art direction, but for now, I'm really excited about my future in Customer Experience.
If you’d like to follow
further, connect with her on LinkedIn and follow her blog, House of CX. 🔗 Reach out to her directly with any questions about career trajectory into CX or kudos for her courage to share her authentic story. | A guest post by
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