Anna Lenhardt specializes in helping startups build and scale to become high-impact companies, drawing from over two decades of experience as an HR professional. She brings a wealth of expertise to HR strategy, operations, technology, and executive coaching, thanks to her distinguished track record as an HR consultant, leader, and executive.
Anna started her career at McKinsey & Company, where she honed her skills, and then served as an HR consultant at Deloitte. Her journey working with startups began as Head of People at Hippo Insurance, where she played a pivotal role in building and scaling the company’s workforce and fostering a vibrant culture, ultimately achieving a successful NYSE debut. Then, as VP of People at Oscar Health, Anna spearheaded People Operations as the company expanded from 250 to over 1,000 employees. Her strategic leadership enabled the organization to scale effectively and prepare for its future IPO.
Before her work with Hippo Insurance and Oscar Health, Anna contributed her expertise to a variety of emerging startups where she established critical HR leadership, developed innovative programs, and built essential processes. Her efforts resulted in helping these businesses secure additional funding, generate revenue, and facilitate company growth for these startups.
Anna is a distinguished scholar, holding separate master's degrees in Counseling Psychology and the Arts. In addition to her professional roles, she contributes her knowledge and insights as an advisory board member for Budgie Health, a company dedicated to providing employees with valuable health claims data to inform better decisions regarding their benefits packages. She also volunteers at Kara, a grief support organization helping teens, children, and families.
"Anna has been an incredible asset to my leadership and up-leveling my skill set and strategy as a people leader. She is a powerful thought partner, an incredible strategist, and someone who understands operational rigor and empathy in building people teams and executive stature in the startup world. I’m incredibly grateful that I was able to leverage Anna as an advisor, mentor, and secret weapon when I needed her most."
Testimonial About
Tailscale - VP, People
