Jessie Roberts
Jessie Roberts (they/them) is a Customer Success Team Lead, Technical Writer, and Support Operations Lead at Clair. They bring over 20 years of experience in customer service, operations, quality assurance, and knowledge management, with a career built around empathy, communication, and systems thinking. From an early age, Jessie demonstrated a strong sense of compassion and emotional intelligence, often stepping in to mediate and bring calm in difficult family situations qualities that naturally evolved into a lifelong commitment to helping others feel heard and supported.
Over the past two decades, Jessie has advanced through progressive leadership roles in call centers and customer service operations, developing deep expertise in scaling support systems and improving customer experience. For the past four and a half years at Clair, a financial technology company, they have worked at the intersection of customer success and AI innovation. In this role, Jessie programs and trains the company’s chatbot using real-world customer service insights, monitors customer feedback and operational trends, reports key performance metrics directly to executive leadership, and serves as a critical bridge between customer support, product development, and design teams.
Jessie is especially proud of building and maintaining a company-wide knowledge base of over 300 articles, along with a comprehensive external FAQ system that improves customer self-service and operational efficiency. Their work reflects a unique ability to scale empathy through technology transforming lived customer experience into digital systems that support thousands of users simultaneously. In today’s evolving digital landscape, Jessie continues to focus on blending human-centered support with AI-driven tools, ensuring customers receive accurate, timely, and compassionate assistance at scale.
• Salt Lake Community College -
Certificate, Fine/Studio Arts, General
• Bloodborne Pathogens
• Top Performing Chatbot recognition from ForeThought
• Helping Women Period
What do you attribute your success to?
I would definitely say self-advocacy and developing my skill set. Having that experience under my belt and really being confident with that experience has been crucial. Being able to let people know the experience that I have and seek out expansions upon my position has made all the difference. It is not just about possessing the skills, but about being able to articulate that experience to others and demonstrate how those skills apply to the broader goals of the organization. By remaining focused on refining my expertise and advocating for my professional advancement, I have been able to navigate my career path with both clarity and purpose.
What’s the best career advice you’ve ever received?
The best advice I ever received was to be louder and advocate for myself. I had a mentor who was very, very successful, and she spent time with me and told me about all of my skills. She said, you have this skill, and you have this skill, and these are great things that any company would be lucky to have. You need to put your best foot forward, and you need to advocate for yourself. As soon as I started taking her advice, it was like a light switch. The tech industry is really hard to get up there as a woman, it is definitely a boys club, and so is FX Makeup. I had experience trying it out in my FX makeup in my off time, and then I was able to just put it full tilt boogie into FinTech, and it was a meteoric rise. It was every 6 months I was getting a promotion. The other critical piece of advice is to document everything. I have a little plaque on my desk that says, but did you document it? Because you can do all of the things, you can create an entire system on a back end, but if you don't write it down, you may not remember all the things that you did. Making sure you document everything makes advocating for yourself a little easier.
What advice would you give to young women entering your industry?
I would say be loud. That is the biggest thing that I see as the difference between men and women in this field. Men will just naturally be doing the work, and because of societal misconceptions, generally they are seen as going above and beyond just because they are being compassionate, whereas a woman in this field could work very hard and not get anywhere because she is not being loud about where she wants to go. So advocating for yourself and being loud are the major things, and knowing where you want to go. You must be intentional about articulating where you want to go and what you want to achieve. It is not enough to simply do the work; you must ensure your contributions are visible and that you are actively negotiating for the positions and titles you deserve.
What are the biggest challenges or opportunities in your field right now?
Right now, one of the biggest challenges is navigating financial landscapes. Currently I work for Clare, which provides wage advance loans to America's workforce, their hourly workforce, generally people who make $60K and under. Some surveys have shown that a large percentage, like 70 to 80% of Americans, are living paycheck to paycheck, and our goal is to assist those individuals. When people have money involved, it just gets so complicated. Trying to find a way to provide these services for people to not get them into a repetitive cycle, to not be predatory, and then to help them with their issues without getting riled by their needs is incredibly challenging. People can get very passionate when you are talking about their money. That is one of our biggest ongoing challenges throughout the industry, to make sure that they are having a good time with it and being able to get themselves out of those paycheck cycles.
What values are most important to you in your work and personal life?
Integrity is number one. If you say it, you should do it. That is the foundation of trust and ensures that colleagues and partners can depend on your contributions and your character. And I would say another one would be transparency. Transparency is equally vital, as it fosters an environment of honesty and open communication. By being clear about intentions, processes, and challenges, we can build stronger relationships and solve problems more effectively. Together, these values create a framework for accountability that leads to more authentic connections and sustainable success in any endeavor.
Locations
Clair
Magna, UT 84044