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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, CA
James hails from Livermore, CA where he has spent the past 14 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.
Logan Alley
Founding Agent, CO
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.
Brett Wightman
Agent
Brett grew up on his family farm in Edinburg, VA, and completed his degree in Agriculture Economics 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.
Dustie Paynter
Agent
Born and raised in Idaho, Dustie has always had a deep respect for the land and the people who work it. Since 2014, she has specialized in crop insurance, building a reputation for delivering dependable risk management solutions to farmers and ranchers across the region. With over a decade of industry experience, Dustie combines practical expertise with a genuine passion for protecting agricultural operations of all sizes. Her hands-on approach and focus on long-term relationships make her a trusted resource in the ag community.
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Outside of work, Dustie enjoys camping in Idaho’s backcountry, riding her RZR through rugged terrain, and spending time with her grandchildren as they care for animals, grow food, and explore the world with wonder.
Tyler Hoopes
Agent
Tyler is a fourth-generation potato farmer and licensed crop insurance agent. Since 2017, he has helped growers across Idaho, Washington, and Utah protect their operations with practical, personalized risk management strategies. His firsthand farming experience gives him a deep understanding of the challenges producers face and how to navigate them.
He and his wife Necia live in Idaho with their four children, enjoying the state’s outdoor lifestyle: snowmobiling in the winter, riding dirt bikes in the summer, and staying rooted in the agricultural community they call home.