About Pretty Smart Insurance

Pretty Smart Insurance was founded by Jennifer Donaldson, a licensed insurance agent, fractional CFO, and trusted advisor with more than 30 years of experience across the financial and health insurance sectors. Built on a foundation of expertise, integrity, and personalized service, Pretty Smart Insurance helps entrepreneurs and small business owners secure tailored health insurance solutions that align with their business goals and long-term vision. Jennifer’s background in both insurance and financial strategy allows her to provide guidance that is practical, informed, and results-driven.

What truly sets Pretty Smart Insurance apart is a genuine commitment to empowering clients to build businesses that reflect their values and aspirations. Whether you are launching a new venture or managing a growing organization, Jennifer offers clear insight, strategic planning, and thoughtful mentorship to help you navigate complex insurance decisions with confidence. Her mission is to simplify the process, support sustainable growth, and help clients move forward with clarity and peace of mind.