While Josefin O’Brien oversaw the filming of dating programs as a TV producer, she was unwittingly building the perfect skill set for a career in customer success.
Between overseeing multi-location shoots and managing production teams, she mastered the arts of clear communication, leading through ambiguity and driving alignment, all of which are critical to building strong, successful relationships. So when O’Brien entered the tech industry and discovered CS, she felt as though she had found the perfect career fit, which ultimately led her to her current position as a senior customer success manager at CertifID.
“Now, instead of elevating a host or a storyline, I’m helping customers succeed,” she told Built In Austin.
O’Brien isn’t the only CS professional who found themselves unexpectedly drawn to the field. Before Clare Peyton stepped into the world of CS, she worked in the sports industry, and while the experience was enriching in its own way, it wasn’t where she wanted to build a long-term career.
After joining a SaaS company, she was introduced to CS, setting her on a fulfilling career journey that would ultimately bring her to Closinglock, where she currently works as a manager of customer success. And while much of Peyton’s professional experience has served her well so far, her background as a certified scrum master has proven to be especially impactful.
“In CS, this has allowed me to more effectively work with product teams, whether it’s organizing and prioritizing client feedback, participating in roadmap discussions or driving feature adoption with customers,” she said.
For both O’Brien and Peyton, diverse professional experiences have served as a catalyst for success in the CS field. Read on to learn about each one’s career journey, the skills they rely on most in their day-to-day work and the advice they’d give to other professionals eager to get started in CS.
Closinglock’s platform is designed to protect real estate transactions by safeguarding money, documents and data.
Tell us about your journey into customer success. What kinds of roles were you in before CS, and what made CS the right choice for your career?
Before I moved into CS, I started my career as an inside sales account executive at Monumental Sports and Entertainment. I was making over 200 cold calls a day, pitching season ticket packages. While I quickly realized that the sports industry wasn’t the long-term path for me, that role taught me persistence, how to handle objections and the importance of clear communication. Wanting to stay in a client-facing role, I pivoted into the SaaS industry and joined Meltwater as an onboarding manager. That’s where I was first introduced to CS. I was responsible for getting clients up and running post-sale, making sure they understood the platform, saw early value and were set up for long-term success. I loved it.
That experience showed me how impactful it can be to build ongoing relationships with customers and help them grow with the product. I realized how much I enjoyed being a strategic partner and celebrating customer wins. My early sales experience gave me confidence in tough conversations and laid the foundation for renewal negotiations and driving retention later on in my CS career. CS ended up being the perfect fit.
What skills, proficiencies or background experience have you found to be most useful for your career in CS? Has anything surprised you?
Strong communication skills across all mediums, whether it’s email, Zoom, Slack or in-person, have been absolutely essential in my career in CS. Being able to clearly articulate value, manage expectations, and align internal and external stakeholders is critical to building trust and driving outcomes. One skill that’s been surprisingly valuable is my background as a certified scrum master. While it’s traditionally associated with product and engineering teams, it’s given me a strong foundation in agile project management and cross-functional collaboration. In CS, this has allowed me to more effectively work with product teams, whether it’s organizing and prioritizing client feedback, participating in roadmap discussions or driving feature adoption with customers. It’s also helped me manage internal initiatives and client onboarding or expansion projects more efficiently. What’s surprised me most is how much CS overlaps with so many functions — sales, product, support and marketing — and how critical it is to be a connector across teams.
“Being able to clearly articulate value, manage expectations, and align internal and external stakeholders is critical to building trust and driving outcomes.”
If you could give any advice to professionals looking to make the move to CS, what advice would you give them?
The best advice I’d give to anyone looking to break into CS is to be proactive about learning from those already in the field. Start by connecting with CS professionals on LinkedIn and reaching out for informational conversations; most people are more than happy to share their experiences and advice. These conversations can give you a better understanding of the day-to-day work, the skills that matter most and how to position your background. I’d also recommend joining CS communities, like Gain Grow Retain, CS Insider or Women in Customer Success, and attending webinars, meetups or local events. Immersing yourself in the space not only helps you build your network but also keeps you up to speed on best practices and trends. Finally, don’t underestimate the value of transferable skills. Whether your background is in sales, support, operations or something entirely different, highlight how your experience aligns with the core of CS: building relationships, solving problems and helping customers succeed.
CertifID aims to prevent real estate wire fraud with its platform, which enables individuals and businesses to verify identity and bank details before transferring funds.
Tell us about your journey into customer success. What kinds of roles were you in before CS, and what made CS the right choice for your career?
Before entering customer success, I built a career in TV production, producing live news, entertainment specials, dating and makeover programs, and even a daytime talk show. My roles ranged from casting and field production to overseeing multi-location shoots, both domestic and international, and managing production teams. I thrived in environments where I had to balance creative vision with logistical precision under tight deadlines. As I moved into tech, I realized I had been doing “customer success” all along, just with a different title. I made the switch officially because it gave me a new way to build meaningful relationships. Now, instead of elevating a host or a storyline, I’m helping customers succeed.
What skills, proficiencies or background experience have you found to be most useful for your career in customer success? Has anything surprised you?
My production background taught me how to plan ahead, pivot quickly, and keep people calm when things go off script, which happens often in both TV and CS. I also learned how to ask the right questions early, which has helped me uncover needs and manage expectations proactively. I’ve been surprised by how much my project management and people skills still serve me daily. In both industries, you’re only as good as your ability to communicate clearly, lead through ambiguity and keep everyone aligned toward a shared goal — even when that goal evolves. I always hoped my experience producing red carpet interviews or makeover shows would support me in my next chapter, and I’m thrilled to see that it has!
“I’ve been surprised by how much my project management and people skills still serve me daily.”
If you could give any advice to professionals looking to make the move to customer success, what advice would you give them?
Don’t underestimate the value of your non-tech experience. If you’re used to working with people, thinking on your feet and translating complex ideas into something approachable, you’re already doing the hard parts. My advice: Learn the language of SaaS, get curious about how products are built, and understand how success is measured in the business. And most importantly, lean into your ability to relate to people. It’s not about being the loudest voice in the room — it’s about being the one your customer trusts when things get tough.
