KAIROS Insurance Group

Kairos Insurance Group is a true family-owned agency with deep roots in the insurance industry. Originally founded in 1992 by Sandee Wilson as First Choice Insurance in Boca Raton, Florida, the business grew through dedication, service, and trust. In 2004, Sandee and her daughter Summer Westerbur opened Aspen Insurance Group in Colorado Springs, which later evolved into Kairos Insurance Group.

After decades of serving clients, Sandee has retired, leaving a proud legacy. A single mother, she raised Summer in the business—Summer learned the ropes working in her mother’s office during high school and has now built on that foundation with over 22 years as a licensed agent. Continuing the family tradition, Summer’s child, Ari Westerbur, has joined the agency part-time, working in Kairos’ expanding cannabis division while completing an undergraduate degree in Ireland.

Today, Kairos Insurance Group remains a boutique, woman- and family-owned firm, specializing in medium to large employer groups and individual exchange plans with subsidies. With the recent addition of Lindsay Amos to the team, Kairos looks forward to continued growth while staying true to its core values of personal service, expertise, and family legacy.