Senior Workers’ Underwriter - Midwest

Remote (U.S.)

Make an Impact where your Expertise Matters

At Insurate, we're building a modern workers' compensation platform rooted in underwriting excellence, strong agency partnerships, and profitable growth. We believe the best underwriting decisions come from experienced professionals with a collaborative mentality utilizing the right tools with autonomy to do what they do best.
We're looking for a Senior Workers' Compensation Underwriter – Midwest to help grow our middle market portfolio through strong agency partnerships to shape the continued evolution of our underwriting organization.
This is more than a production underwriting role. You'll be trusted to make sound underwriting decisions, collaborate directly with leadership, influence underwriting processes, and help drive profitable growth. If you're an experienced underwriter who enjoys partnering with agents to help analyze complex risks while working in an entrepreneurial environment where your ideas matter, we'd love to hear from you.

As a Senior Workers' Compensation Underwriter, you'll independently manage a profitable middle market book while partnering closely with agency partners, Business Development Executives, the MGA Program Director, Claims, and executive leadership.

Responsibilities will include:

• Underwriting and managing a Midwest-focused middle market portfolio, including accounts ranging from $50,000 to $1M+ in annual premium
• Underwriting nationwide workers' compensation business submitted through agency partners
• Evaluating and structuring both guaranteed cost and deductible programs
• Performing comprehensive underwriting analysis, including Operational and exposure review, classification and payroll validation, experience modification analysis, loss run and claim narrative review
• Developing thoughtful underwriting positions, pricing strategies, coverage terms, and referral documentation
• Collaborating with Claims on complex accounts and open claim reviews
• Building strong relationships with agency partners through responsive communication and sound underwriting expertise
• Partnering with Business Development Executives to evaluate opportunities, provide underwriting guidance, and support profitable agency growth
• Collaborating with the MGA Program Director on program strategy, agency development, and portfolio management initiatives
• Identifying opportunities to improve underwriting workflows, operational processes, and overall efficiency
• Contributing ideas that strengthen underwriting quality while supporting profitable company growth

You're an experienced workers' compensation underwriter who combines strong technical expertise with sound judgment and a collaborative mindset. You enjoy building strong relationships while helping to solve complex risks through thoughtful underwriting decisions that balance growth with profitability.
You thrive in an entrepreneurial environment where you're trusted to work independently, contribute ideas, and continuously improve the way underwriting gets done.
You're comfortable making independent underwriting decisions, asking thoughtful questions when needed, and partnering across the organization to achieve the best outcome for our agents, insureds, and the business.

• 5+ years of Workers' Compensation underwriting experience
• Strong expertise underwriting workers' compensation business across key Midwestern states, including IL, IN, IA, KS, MI, MN, MO, NE, SD, and WI
• Demonstrated success underwriting middle market accounts
• Experience underwriting:
  High Hazard Operations, Construction risks, multi-state and multi-entity exposures, Guaranteed cost and Deductible Programs
• Strong analytical and decision-making skills with the ability to confidently communicate and support underwriting decisions
• Excellent communication skills with brokers, agency partners, and executive leadership
• Self-motivated with the ability to work independently in a remote environment
• Comfortable balancing multiple priorities in a fast-paced, growth-oriented organization
• Collaborative, solutions-oriented mindset with a desire to continuously improve processes and help those around you succeed

At Insurate, we invest in technology that allows our underwriters to spend less time on administrative work and more time doing what they do best—analyzing risk, making thoughtful decisions, and building strong agency relationships.

You'll regularly work with:

• Microsoft Teams and Microsoft 365
• Proprietary submission and…