A little over a year ago, I made the leap from banking to surety underwriting. I didn’t have a clear roadmap — just a job listing, a little research and an open mind. I quickly discovered that the surety world is far more dynamic and rewarding than I initially imagined.
How I Got Here
I spent 8.5 years in banking, mostly in commercial and mortgage lending. When mortgage rates started climbing, I began looking for a new opportunity and came across a listing for a contract surety underwriter role. I didn’t know much about the field, but after meeting with my now-supervisor, Andrew, and doing some deeper research, I realized the industry played well to the skills I had developed: relationship-building, risk analysis and attention to detail.
What I Thought Underwriting Was (and What It Actually Is)
Coming from banking, I assumed underwriting meant being buried in the back office, reviewing documents with minimal client interaction. That’s how it was at the bank — underwriters were behind the scenes, rarely meeting customers or agents.
That was my biggest misconception.
Surety underwriting, especially at Old Republic Surety, is hands-on and highly relational. We attend networking events, make sales calls and spend real time with agents and contractors. The relationship-building aspect — what I’ve always enjoyed — turns out to be central to the job.
The Skills That Carried Over
Banking prepared me well for this transition. I had a strong foundation in risk management and financial analysis. Those skills help me evaluate work-in-progress schedules, assess contract risk and make sound decisions that benefit both the company and our clients. I also brought experience in networking and new business development — two things that are critical in surety.
One of the biggest things I’ve learned in year one: You have to be able to have honest conversations. It’s not about rubber-stamping every project. Sometimes you have to tell a contractor that a job doesn’t make sense and that you’re looking out for everyone’s long-term success, not just the next approval.
A Memorable Milestone
Completing our formal training program was a major accomplishment. It included multiple weeks of classroom-style sessions, case studies and testing at our Brookfield, Wis. office. It was fast-paced and information-heavy, and it gave me the tools I needed to hit the ground running. Being able to apply what I learned to real-world accounts was a great feeling and a reminder that the investment in training was worth it.
Culture Makes the Difference
One of the best parts of my first year has been the culture at ORS. From day one, I felt like I was part of a team. Everyone — from our local office to senior leaders at headquarters — has been welcoming, available and genuinely interested in helping me grow.
Even outside the company, the surety community has been incredibly open. It’s a niche industry and in many ways, it feels like a small town. People know each other and relationships matter. I’ve met other underwriters, agents and professionals who’ve all been more than willing to share advice and insight.
And it’s not just professional support that makes the culture strong. ORS promotes work-life balance and flexibility, including the ability to work remotely part of the week. That has made it easier to be present for my family while still investing fully in my career.
Lessons Learned and What’s Next
The biggest lesson from year one? Be a sponge. Ask questions. Listen. Whether you’re in a meeting with leadership, an agent or a contractor, there’s always something to learn. And preparation is key: Understanding your accounts and anticipating questions can make a big difference in how relationships evolve.
Looking ahead, I’m excited to grow my own book of business. I’m focused on building lasting relationships with agents and contractors, learning more about the construction industry, and gaining confidence in making decisions that shape deals from start to finish.
Surety isn’t a career I planned for, but it’s one I’m glad I found. If you enjoy building trust, solving problems and making meaningful connections, it’s absolutely worth exploring.
