Finance at the Jobsite

How Surety Underwriters Really Think: Cash Flow, Risk & Smart Growth in Construction


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What does a surety underwriter actually look for when deciding whether to support a contractor?

In this episode of Finance at the Jobsite, host Rishi Srivastava sits down with Jacob Studer, Construction Surety Bond Underwriter at Travelers, to unpack how bonding decisions are really made — beyond ratios and checklists.

Jacob brings a rare perspective, having worked in the field as a framer and electrician, run his own contracting businesses, and now underwrite bonds for contractors nationwide. That hands-on background shapes how he evaluates risk, character, and long-term potential.

In this conversation, we cover:

  • The 3 non-negotiables underwriters care about most (character, cash flow, and operating margin)

  • Why one bad project can take down an otherwise healthy contractor

  • How surety underwriting differs from insurance and mortgage lending

  • What contractors can do to earn support even with imperfect financials

  • Why WIP accuracy and financial discipline matter more than revenue

  • How contractors should think about stretch jobs and bonding capacity

  • Practical ways AI and automation can make contractors more bondable today

If you’re a contractor, CFO, controller, or advisor looking to grow safely — this episode is a must-listen.

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Finance at the JobsiteBy Rishi Srivastava