Anna Olenick

Anna thrives on keeping complex lives running smoothly. As Wingspan’s Onsite Executive Assistant and Household Manager, she brings a blend of precision, adaptability, and humor to every detail—ensuring Cathy, Ivan, and the entire team focus where it matters most.

Known for juggling it all with ease (sometimes literally—calendars, schedules, and grocery bags in one trip), Anna has a talent for creating structure that feels effortless. She anticipates needs before they’re spoken, keeps operations tight, and ensures clients feel genuinely supported along the way.

Her work is fueled by curiosity, connection, and the satisfaction of lightening the load for others. She believes that when leaders are freed from distractions, they drive impact with clarity and confidence—and she’s proud to play a role in that mission at Wingspan.

When she’s not streamlining systems or keeping the team on track, you’ll find Anna outdoors with her pup Rue, hiking, traveling to visit family and friends, or sharing good food with people she loves. She brings the same intentionality, warmth, and lighthearted energy into her personal life that she carries into her role at Wingspan.