Her Story
About Kaitlin
Kaitlin Zidar is a People Strategy and Solutions professional at Thatch, where she focuses on helping employers design and execute forward-thinking benefits strategies that align with broader organizational goals. She partners with organizations of all sizes to support both short-term and long-term benefits planning, viewing employee benefits as an integral component of total compensation and overall people strategy. Her work emphasizes the importance of aligning salary, bonus, equity, and benefits into a cohesive package that enhances employee understanding and strengthens the employer value proposition.
Her career in insurance and employee benefits began at Aon in Chicago, where she developed an early interest in the complexity of insurance regulations and systems. Driven by curiosity, she created her own unconventional career path, transitioning from insurance consulting into ad tech to gain technical experience working with APIs and digital infrastructure. Over time, she recognized her strongest interest remained in employee benefits, where the impact on individuals is both tangible and meaningful. This realization led her to roles in HR compensation, where she gained a deeper understanding of how benefits function as part of a holistic compensation philosophy.
She later joined Sequoia Consulting Group, where she contributed to growing the New York office’s book of business while playing an active role in operations and product development. At Level, she helped advance fintech-driven solutions aimed at reducing inefficiencies within the insurance and benefits ecosystem. After relocating to Austin, she advised large enterprise clients, including Salesforce, HP, and HPE, gaining valuable experience in population health strategy and large-scale benefits design. Today at Thatch, she is focused on modernizing the employee benefits experience by bringing a consumer-grade, technology-driven approach to insurance enrollment, making it more intuitive, transparent, and aligned with how people shop for and experience modern services.
Her Interview
Ten minutes with Kaitlin
01What do you attribute your success to?
I attribute my success to a combination of curiosity, consistency, and a commitment to improving systems that impact people’s lives. At Thatch, I’m driven by our mission to build a healthcare system people love, and to help advance the first Individual Coverage Health Reimbursement Arrangement (ICHRA) platform. Joining the organization during its Series B stage, I’ve been energized by the opportunity to grow alongside a high-performing team in a fast-moving environment. My experience across employee benefits, HR consulting, and insurance technology has strengthened my ability to translate complex challenges into practical, scalable solutions.
02What advice would you give to young women entering your industry?
It is a long journey, and there will be unforeseen bumps in the road. Each bump is an opportunity to learn and polish yourself, while keeping a broad perspective. I would recommend to follow your curiosity because the only constant is change. The more solid your understanding is of the fundamentals, the better you will be when you get to the more advanced application. I would also add that this space of benefits and insurance is all applied psychology. When you have that mindset and look at the different pieces of psychology, people are very predictable. We are irrational animals and we don't always make the best decisions for ourselves, so providing the appropriate guidance and context helps with the change management. People don't like change, but being the professional that can guide that is where I found a lot of steadiness, despite all of what could be perceived as chaos. Benefits is a relationships business.
03What values are most important to you in your work and personal life?
I really try to focus on taking care of myself with working out in the morning and eating balanced meals. It's about keeping things in perspective, because a project that's really stressful is temporary, so I remind myself that high-stress moments are temporary. I also lean on the team I have around me. I'm very grateful that I've worked with a lot of talented people and learned from them as well, but also leaned on them, because you don't have to do it alone. I have a community that I've built and the family that I have, and having that support psychologically and mentally is very humbling during challenging moments. I'm also a big believer of working hard and playing hard, because you have to bond with the people you work with, not just through Zoom, but also be human about it. This is a relationship-driven business, and I still talk to people that I started my career with 13 years ago because of getting out from behind a computer and doing things together. I also believe in willingness to learn from everyone. The most senior person in the room, as well as the most junior person in the room, can teach you something, and that humility also helps.
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