From Trainee to VP: Doug Brekke's Underwriting Career in Commercial Insurance

From his early days as a trainee to his current role shaping innovative strategies, Doug Brekke’s experience highlights the multifaceted work of underwriting, where intricate risk assessment, financial analysis, and strategic decision-making come together in his role as vice president of commercial product and underwriting at SageSure.

Uncover more about what an underwriter does and the parallels Doug finds between his underwriting career and his passion for racing sports cars.

What Motivated You to Pursue an Underwriting Career?

Growing up in the Los Angeles suburbs, opportunities in the insurance sector were abundant. My mom spent most of her professional career at a large health insurance provider, so I’d hear about what the general insurance world was like. Many of her friends were health insurance underwriters, and I found them to be smart, curious, and informed people who made a good living, so the underwriting discipline planted a seed of possibility for me as a pathway to my ultimate goal of people and business leadership.

What Route Did You Take to the Insurance Industry, and What Is Your Background/Degree?

A few years after graduating college with a business management degree, I began my commercial insurance career with a small regional carrier as an underwriting trainee. While I certainly didn’t know what I didn’t know, which was a lot, I brought ambition, drive, and desire to learn everything I could about the world of underwriting and the commercial insurance industry. The company invested significantly in my development, and I was able to experience the roles of a production underwriter, senior underwriter, and underwriting supervisor early on in my career, which gave me an accelerated perspective of the exciting path ahead. I’m grateful for the individuals who saw something in me worth making a bet on.

Tell Us About Your Background and Experience as an Underwriter.

I’m a naturally curious, contemplative person who wants to understand the why behind whatever I’m focused on, which I quickly learned are characteristics integral to the role of an underwriter. Over my 23-year career in commercial underwriting, I’ve worked at regional and national carriers, in home office and field roles, with small commercial and middle-market business units, and within captive and independent agency distribution models, traveling to many of the 50 states to learn the environment I was underwriting. The richness of diversity of these experiences has shaped my perspectives on the business, art, and science of underwriting.

SageSure Is Known for Its Rigorous Underwriting Practices. What Makes Our Strategy So Great Overall?

When you’re in the business of insuring underserved markets, you need a best-in-class underwriting approach. The combination of our proprietary catastrophe modeling insights, our highly granular approach to risk segmentation, our experienced group of underwriting professionals, and the investment we make in inspecting every risk we write allows us to make thoughtful underwriting decisions that benefit our carriers and customers alike. This rigor positions SageSure to serve customers in coastal states as a long-term, trusted insurance provider.

What Does an Underwriter Do, and Why Is the Role of an Underwriter So Crucial in Insurance?

Being an automotive enthusiast, I’ll use a metaphor to answer the question in terms of driving a car. Our sales team is responsible for pressing the gas pedal to move us forward. Our actuarial group looks in the rearview mirror to understand what hazards we may encounter ahead based on the road already traveled. Our corporate risk management team is watching exposure concentrations to know when to pump the brakes. All the while, underwriting is managing the steering wheel, taking the feedback from these various stakeholders to know which way to steer on a deal-by-deal and portfolio basis. The underwriter also brings unique insights on an individual-risk basis that models and tools may not perfectly contemplate. This ensures we make smart risk-based decisions while providing a feedback loop to strengthen our models’ predictiveness over time.

How Do You Stay Updated with Industry Trends and Changes in Regulations Affecting Underwriting?

Proactively plugging into as many media sources as possible, including following key competitors on LinkedIn, subscribing to trade publications, joining topical industry webinars, and signing up for regulatory mailers is an effective way to ensure the right information is fed to you. Additionally, maintaining an active professional network across various insurance companies and distributors ensures you’re a part of the right conversations.

In Your Opinion, What Are the Most Important Qualities or Skills for a Successful Underwriter?

At SageSure, we talk about underwriting as an art and science. That means folks who enjoy tapping both sides of their brain will thrive in this role. This involves creativity in assessing and structuring risk, investing in relationships, and leveraging emotional intelligence in communicating decisions. It also means being a curious risk analyzer, a strategist who can balance core business objectives on a deal-by-deal basis, and someone who can make smart risk-based decisions. Combined, these attributes create the right recipe for generating desired outcomes for SageSure, our agents, policyholders, investors, and carrier partners.

How Do You Collaborate with Other Departments or Colleagues, Such as Claims or Sales?

At SageSure, we’re an intentionally flat and collaborative organization, so we’re naturally inclusive by seeking out a variety of departments’ thoughts to ensure we’re making the right decisions. Being collaborative is not something we have to force; rather, it’s part of the DNA of how we operate as an organization, which makes coming to work feel energizing. No matter what challenge we face, we face it together and are determined to find a way forward.

Can You Discuss Any Advancements or Innovations in Underwriting Technology or Methodologies That You Find Particularly Exciting?

The rapidly evolving technology of artificial intelligence (AI) is particularly exciting and something I watch closely. AI’s evolution brings new ways for underwriters to make highly informed decisions in a shorter timeframe. Instead of spending our time finding and assembling information to make decisions, the effective integration of the right type of AI at the right point of the workflow process can repurpose the underwriter’s time toward making more decisions versus spending time managing administrative tasks, which results in better business outcomes for all stakeholders.

Is Underwriting a Good Career, and What Advice Would You Give to Someone Considering an Underwriting Career?

Consider it! The insurance industry is one of the few industries largely insulated from economic cycles, as there’s a built-in demand for insurance products in our economy, which offers a good amount of career opportunity and job security. The richness of diverse experiences in our industry is second to none, yet somehow this fact remains a best-kept secret. The variety of underwriting experiences, specifically underwriting roles by business type, business size, and coverage need are vast and offer a dynamic path for a growth-minded individual who wants to make their mark on an industry that plays an integral role in keeping society functioning.

What Excites You Most About What’s Happening at SageSure?

Being a technology-focused, insurance-first organization, the rate of innovation at SageSure is like nothing I’ve experienced. It’s incredibly energizing to make decisions to improve our product design or customer experience in real time, versus the red tape and politics that hamper more traditional carrier organizational models. Everyone at SageSure is passionate about their craft, and we are self-motivated to “run down the hall” to produce optimal outcomes. Considering our Commercial Insurance group specifically, the opportunity to be a part of building a best-in-class commercial insurance provider for underserved coastal markets is as exciting as it gets!

What Do You Enjoy Doing When You’re Not Working?

I spend most of my free time as a proud girl dad to two grade schoolers, keeping up with their extracurricular activities, enjoying all that Colorado life offers, and traveling as a family. When I get my alone time, I’m an avid sports car racer in some time trial/autocross championship series, feeding my passion for speed, continuous self-improvement, and—of course, as an underwriter—calculated risk-taking.