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Who We Are
Till is a team of agents, farmers and financial analysts with experience in insurance, investing, and marketing at organizations such as Syngenta, Farmers Business Network, and Google.
James Bennett
Founding Agent
James hails from Livermore, CA where he has spent the past 13 years working in the insurance industry. His roles have spanned from loss control to underwriting and finally as an agent focusing solely on crop insurance for the past 7 years. This experience across multiple roles within the industry gives James a unique knowledge base from which he can advise his clients on the optimal risk strategy.
Besides crop insurance, James, his wife Kelsie, and daughter Blair, own and operate 7Z Livestock. They enjoy raising sheep that get shown all over the country and working with the next generation of agriculturalists.
Callum Woolley
Founding Partner & Agent
Callum brings a background in climate risk management, with experience at Google and the World Bank. Before starting Till, Callum led climate risk and AI teams focused on pricing risk of weather-related perils. At Till, Callum is dedicated to improving the agent experience through streamlined application, AR and PR processing workflows, as well as FCIC policy analysis.
Callum holds a graduate degree in environmental economics from the University of Cambridge.
Tom Cole
Founding Partner
Tom has a background in investing, having worked at Cyrus Capital, where he focused on valuing and trading stocks, bonds and corporate credit insurance. Tom started his career in Millstein & Co.’s restructuring practice, where he worked on corporate and sovereign financial restructurings.
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Tom holds a BA in political science from Duke University, where he was a Robertson Scholar, and an MBA from Harvard Business School.
Brett Wightman
Agent
Brett grew up on his family farm in Edinburg, VA, and completed his degree in Agriculture Economics degree at Virginia Tech in 2008. He began his career in the field of agriculture with Syngenta Crop Protection.
After helping growers and retailers throughout the region troubleshoot crop protection solutions and navigating seed decisions for almost six years, Brett decided to switch gears and begin his crop insurance career. Brett serves farmers in VA, WV, NC, MD, TN, MO, KY, and KS.
Logan Alley
Agent
Logan is a fourth-generation cattle rancher from southeastern Colorado with deep roots in agriculture and a strong commitment to family and community. He holds a finance degree from Colorado State University and has spent the past decade as managing director at a Colorado Springs investment advisory firm. As a crop insurance agent with 8+ years of experience, Logan is passionate about risk management strategies that support long-term farm sustainability.
He lives on his family’s ranch with his wife, Jayci, and their four children, and is active in local youth sports and nonprofit leadership.