Expertise:
- National inspector network strategy and engagement
- Alternative inspection solutions field operations
- Fulfillment optimization and process design
- Leadership development and team development
A foundation built on fulfillment
Thomas Fleming's career began after he earned a bachelor's degree in business management and a minor in history from the University of Oklahoma. His early experience in the startup world involved managing large-scale fulfillment logistics and supplier partnerships. Impressively, he helped grow an e-commerce supplier base from five to 125 vendors, fulfilling more than 20,000 monthly orders. This experience laid the groundwork for a smooth transition into the world of inspections and claims support.
Thomas joined WeGoLook, a Crawford & Company subsidiary, in 2018. With over seven years of excellence and a career rooted in operational efficiency, he now serves as the director of community at WeGoLook. In this pivotal role, Thomas leads the growth, health and performance of the company’s 1099 inspector network, supporting the delivery of Alternative Inspection Solutions (AIS) nationwide.
Expanding reach and raising standards
After joining Crawford, Thomas spent several years managing five different areas of business, gaining deep exposure to operations, strategy and team development. His leadership in standardizing key workflows and implementing metrics helped shape Crawford’s scalable fulfillment engine. In May 2023, he was promoted to his current role as director of community. Thomas oversees the end-to-end management of Crawford’s national 1099 network of Lookers, property inspectors and roof inspectors. His team is responsible for onboarding, supporting and optimizing the performance of inspectors across a broad range of assignments, from basic auto checks to assisted roof assessments and commercial site surveys.
“We’ve built a team that’s not just experienced but deeply committed to the mission.” - Thomas Fleming
Making an impact through leadership
Thomas credits much of his growth to Crawford’s emphasis on people development. In 2023, he was selected for the company’s Emerging Leaders Program, which allowed him to build relationships with cross-functional peers, strengthen his leadership style and deepen his alignment with the company’s long-term strategy. He takes special pride in helping create scalable, tech-supported processes that serve both internal teams and client needs. Whether determining KPIs, coaching inspectors or enhancing workflows, Thomas maintains a clear focus: strengthening Crawford’s inspection infrastructure while supporting those who bring it to life every day.
Eyes on the future
There is immense opportunity in the continued growth of AIS. As inspection volume rises and client expectations evolve, Thomas and his team are working to deliver faster, more accurate solutions backed by the agility of WeGoLook’s platform and the strength of a nationwide network.
“Whether it is a complex inspection or a straightforward assignment, we show up with professionalism, purpose and precision.”
- Thomas Fleming
Looking ahead, Thomas is focused on expanding service segments, strengthening field engagement and helping Crawford remain at the forefront of inspection innovation.
To learn more about Crawford’s Alternative Inspection Solutions or WeGoLook, please contact Thomas Fleming at thomas.fleming@wegolook.com or visit our Alternative Inspection Solutions service page.
