Six surety underwriting trainees, each with zero to three years in the business, sit outside Brock Masterson’s office in Morristown, New Jersey. Beside them sit four executive underwriters averaging 25 years of experience. For Masterson (pictured), senior vice president and chief operating officer of the surety division at Crum & Forster, that seating plan is the transformation that matters most.
Technology has cut surety decisions from weeks to hours. But in a credit business built on judgment and decades-long relationships, Masterson argues the scarcest asset is experience, and the job is moving it to the next generation.
“At Crum & Forster, our value proposition, how we differentiate ourselves in a very crowded surety marketplace, is the talent we have. The human capital makes all the difference,” Masterson said. “The industry is navigating a shortage of experienced surety professionals, and there are more market participants competing for a limited pool of seasoned underwriters. A major focus for us is transferring knowledge from experienced professionals to the next generation, and that takes time.”
Masterson spent 23 years in underwriting roles at Chubb before Crum & Forster named him to the newly created COO role in late 2023. He holds the Associate in Fidelity and Surety Bonding (AFSB) and Chartered Property Casualty Underwriter (CPCU) designations.
“Nobody goes to university to study surety. There are very few transferable skills from other industries,” he said. “This is an industry of trial and error – your surety knowledge is based on your experiences.”
He describes surety as a credit product designed to produce zero losses, underwritten one account at a time on capital, capacity and character. Financial analysis and credit reports can measure the first two. The third cannot.
“That is where underwriting cannot be replaced by an AI model – and it’s the most prevalent part of the work.”
“While you can assess financial acumen via software, how do you assess leadership skills? How do you assess grit or perseverance in times of struggle?” he said.
That judgment rests on institutional memory. “As the saying goes, those who forget history are doomed to repeat it. That’s very relevant in a credit industry,” Masterson said. “We need to be laying out the pitfalls and the ‘whys’ – why we do certain things – for the younger generation.”
When Masterson started in 2000, agents mailed hard-copy financials to field offices and a decision could take four to six weeks. Today, he said, a 24- to 48-hour response is acceptable for even complex submissions. Crum & Forster’s underwriters now use cash flow forecasting software and AI contract review tools that flag terms needing closer scrutiny.
He has also built his own tool. “I’ve built my own AI prompt that sends me an email every morning laying out everything that happened in the past day that could impact the construction and surety industries – court case reviews, legal reviews, project awards, bankruptcies – and tells me why each item is relevant to surety,” he said.
For trainees, that briefing changes the conversations they can hold with contractors and surety agents about rising costs, supply chains, and labor scarcity.
“That’s how we use AI to boost less experienced underwriters – accelerating their training and the value of their conversations by giving them access to data that previously took a 25-plus-year career to accumulate.”
The trainees will inherit a split market. Masterson said that while data centers and other mega-projects remain areas of significant activity, some other segments of US construction are experiencing softer conditions. According to an Associated Builders and Contractors analysis of US Census Bureau data, data center construction spending rose more than 73% in the 12 months to August 2026.
Contractors are stretching into larger work than they have performed before, while private equity rolls up trade contractors and family firms shift to outside owners or employee stock ownership plans.
“Surety relationships should last decades, but decade-long relationships require trust and consistency,” Masterson said. “Some of the surety bonds outstanding could last longer than the investment horizon of a private equity company.”
Those are the calls the trainees outside his office will eventually make alone, in shortfall. “If we’re doing our jobs as surety underwriters, we should be a trusted advisor to our customers,” he said. “To do that, we need both construction industry knowledge and surety industry knowledge.”
