Discover how HAI Group’s front desk served as a launching pad for successful careers across IT, finance, underwriting, and more. Real stories of growth and opportunity.
From IT and finance to underwriting and operations, these employees embraced learning opportunities, built strong relationships, and found their path forward. While each story is unique, they share a common thread: HAI Group is a place where people grow.
Here are just a few of the many inspiring journeys that started at the front desk and evolved into something more. Responses have been edited for clarity and length.I joined HAI Group in 1989 as an administrative assistant at the front desk. At the time, the company was still fairly new, but a conversation with Sherry Sullivan—currently HAI Group’s chief insurance officer and, at the time, one of the company’s earliest employees working in the underwriting department—about its mission and vision convinced me it was the right place to grow my career. The company’s dedication to making a meaningful impact in public housing resonated with me—I knew I wanted to be part of a team with purpose.
My career has been a journey of continuous learning and taking on new challenges. I transitioned through several roles—including insurance service representative, assistant underwriter, underwriter, senior underwriter, underwriting manager, and assistant director of underwriting—before becoming director.
I embraced cross-departmental projects, sought out mentorship, and developed new skills through training programs. Stepping outside my comfort zone—and the support of my colleagues—helped me get where
I am today.
Starting at the front desk gave me a strong foundation in communication, problem-solving, and relationship-building. It helped her understand how different departments work together and taught her the importance of adaptability—skills that have been crucial throughout her career.
My biggest piece of advice is to stay curious and proactive. Learn as much as you can about the company, ask questions, and seek opportunities to get involved beyond your day-to-day tasks.
I relocated to Cheshire from Massachusetts and wanted to return to work as my son started kindergarten. I found a fill-in receptionist role at HAI Group through a temp agency—and that temporary opportunity turned into a long and fulfilling career.
I was hired full-time in 2003 as an executive assistant, supporting governance, managing the front desk, ordering supplies, and overseeing facilities. That broad exposure helped me build strong connections. In 2012, I moved to the software development company as a senior admin assistant, then became a client solutions rep. In 2017, I transitioned to IT and found my niche. Today, I lead the Service Desk team, helping employees and contractors with their IT needs.
Starting at the front desk gave me a chance to build relationships, sharpen her organizational skills, and gain a deep understanding of how the company operates—skills that continued to support her through every stage of her career.
There may not be a clear ladder for moving up, but there are always opportunities to grow, learn, and evolve your role into something more.
I joined during a challenging job market—after sending out over 100 resumes, HAI Group was my only interview. It turned out to be the perfect opportunity, launching a career I’m proud of.
I started at the front desk, then became an executive assistant. While working full time, I earned a bachelor’s degree and two master’s degrees in IT and management. Thanks to HAI Group’s tuition reimbursement program and a supportive work-life balance, I moved into IT as a project manager and now serve as a senior business systems analyst.
Working at the front desk and later as an executive assistant gave me insight into nearly every department. Handling board packets, assisting with department workloads, and daily administrative tasks gave her a strong understanding of company operations—knowledge that now helps her design and troubleshoot business systems efficiently.
Take advantage of the professional development and educational benefits that the company offers. Don’t be afraid to let others know when you have interest in another area—initiate discussions about possible opportunities.
I joined HAI Group in 2020 as a part-time receptionist. After working evenings in a hospital emergency room, she was looking for stability and better work-life balance—especially as a parent. The front desk role offered both, along with a chance to build valuable experience in a new setting.
Just two months in, the pandemic temporarily closed the office, and I jumped at the chance to take on new responsibilities. Within a year, I became a full-time Business Support Associate, followed by promotions to senior associate and now manager of the Enterprise Support Team. Relationships and mentorship—especially from Trevor Horn—were key to my success.
My time at the front desk gave her a strong foundation in communication, organization, and relationship-building—skills that helped me grow into leadership. It also allowed me to develop a deep understanding of the company and its employees, which proved invaluable in her career progression.
The front desk is the heart of many organizations. Learn the basics, ask questions, stay curious, and take initiative.
Fresh out of college, I joined as a Business Support Associate. I was still exploring my career path, and the front desk offered the perfect opportunity to get exposure, build confidence, and connect with colleagues across departments.
Through my front desk work, I got involved with finance tasks like processing checks and sending invoices. I became interested in billing and accounts payable. My manager, Heather Cibula, and assistant director, Trevor Horn, supported me with finance projects and helped me transition into my current role.
It gave me a solid foundation in communication and project management, and daily chances to collaborate with different teams—experiences that shaped my confidence and direction.
Be open to learning about other departments and take on new projects—it may help you discover what you’re passionate about.
I started as a temp, helping with backend data work in online training. With a background in library sciences, I enjoyed the work and quickly connected with my manager. When a front desk role opened, I saw a chance to grow. Just a few months later, a customer success role became available, and with support from mentors and colleagues, I made the transition.
Four months after moving to the front desk, I became a customer success specialist in online training. I sought mentorship, embraced new learning opportunities, and applied my skills in both data and customer service to find the right fit.
Working at the front desk gave me firsthand experience interacting with different departments, developing adaptability, and learning how the company operates. My willingness to learn, unlearn, and grow helped me navigate new opportunities.
Be open to learning, unlearning, and growing. Embrace new experiences, challenge your own knowledge, and use every opportunity to discover what truly excites and motivates you.
These aren’t just career stories—they’re a reflection of what’s possible when people are encouraged to learn, connect, and pursue what fulfills them. At HAI Group, growth comes in many forms, and everyone’s path is respected.
Whether you’re just starting out or thinking about your next move, remember: You’re in a place that values curiosity, initiative, and people who want to make a difference.
Looking for a workplace that invests in its people? Explore career opportunities at HAI Group!
This article is for general information only. HAI Group® makes no representation or warranty about the accuracy or applicability of this information for any particular use or circumstance. Your use of this information is at your own discretion and risk. HAI Group® and any author or contributor identified herein assume no responsibility for your use of this information. You should consult with your attorney or subject matter advisor before adopting any risk management strategy or policy.
HAI Group® is a marketing name used to refer to insurers, a producer, and related service providers affiliated through a common mission, management, and governance. Property-casualty insurance and related services are written or provided by Housing Authority Property Insurance, A Mutual Company; Housing Enterprise Insurance Company, Inc.; Housing Specialty Insurance Company, Inc.; Housing Investment Group, Inc.; and Housing Insurance Services (DBA Housing Insurance Agency Services in NY and MI).