About Us

Jennifer Donaldson, a licensed insurance agent, fractional CFO, and the founder of Pretty Smart Insurance and Pretty Smart Accounting. With over 30 years of expertise in the financial and health insurance sectors, Jennifer has earned a stellar reputation for guiding entrepreneurs and small business owners toward success with tailored health insurance solutions, strategic financial planning, and insightful business mentorship.

What truly distinguishes Jennifer is her heartfelt commitment to empowering others to build businesses that reflect their personal values and aspirations. Whether you’re dreaming of launching your own business or already managing one, Jennifer’s deep knowledge of health insurance and financial strategies will help you build your business and navigate its complexities with confidence and ease, paving the way for swift and sustainable success.

Jennifer is truly passionate about her work—so much so that, without her husband’s gentle nudging to enjoy some downtime, she’d be helping clients around the clock! Outside of her professional life, Jennifer treasures moments spent with her three children, two bonus children, and five grandchildren, often exploring historic sites together as a family.

Jennifer has masterfully balanced running her thriving businesses, mentoring others to achieve their dreams, and prioritizing what matters most—family and personal fulfillment. She is a genuine role model, and can’t wait to get to know you!