Levi McCrady

About Levi McCrady

I spent five years as a senior underwriter at Chubb in New York before coming back to Pittsburgh to join my family\'s firm. That\'s an unusual path — most people go the other direction — and it shapes how I do this job. When you\'ve sat on the carrier side and seen how underwriters actually evaluate risk, price accounts, and decide where coverage ends, you look at client exposures differently. Most advisors have never read a policy from that chair. I have. At Simpson & McCrady, I work primarily with private companies, nonprofits, and organizations navigating complex or emerging risk — management liability, cyber, professional liability, financial lines. Our firm has been doing this for three generations and insures $10B+ in assets across all 50 states and 23 countries. I\'m not going to tell you insurance is the most exciting thing in the world. But the gap between what most businesses think they have and what they actually have tends to get very expensive very fast. That gap is what I focus on. If you want to talk risk — genuinely talk through it, not get pitched — I\'m easy to find.

Experience

1. Account Executive

   Simpson Mccrady, Llc

   Apr 2025 — Present · Pittsburgh, PA, US

   Risk Advisor (Account Executive) at Simpson & McCrady. Third-generation firm, 45 people,$10B+ in insured assets. I focus on management liability, cyber risk, property and professional lines for private companies, PE-backed businesses, and nonprofits. My edge is that I came from the carrier side — I know how the other half thinks.

Education

• Brown University

  Bachelor's degree, Economics, Political Science

  2016 — 2020