Senior Workers’ Compensation Underwriter - Midwest

Insurate Inc.; Northern (KY); Hybrid; USD 115,000 - 150,000; Full time

Benefits offered by this job

Comprehensive medical, dental, and vis

401(k) Plan

Paid Time Off

Internet/phone reimbursement up to $/€

Equity participation

Remote-first work environment

Job summary

Insurate is seeking a Senior Workers' Compensation Underwriter – Midwest to grow a profitable middle market portfolio with strong agency partnerships. You’ll make sound underwriting decisions, collaborate with leadership, and help drive growth in a remote, high-autonomy environment.

You will evaluate complex risks, work with Claims, Loss Control, and executives to improve processes, and guide pricing strategies while balancing growth with profitability.

Qualifications

• 5+ years of workers' compensation underwriting experience.
• Strong underwriting expertise across Midwest states (IL, IN, IA, KS, MI, MN, MO, NE, SD, WI).
• Experience underwriting middle market accounts (50k–1M+).

Responsibilities

• Underwrite a profitable Midwest middle market portfolio.
• Underwrite nationwide workers' compensation through agency partners.
• Evaluate guaranteed cost and deductible programs.
• Collaborate with Claims, Loss Control and agency partners.
• Partner with Business Development Executives and MGA Director to support growth.

Skills

Underwriting

Analytical skills

Communication

Agency partnerships

Remote work

Tools

Microsoft Teams

Proprietary submission portal

OCR tech

AI-assisted underwriting tools

Job description

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.

What You'll Do

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

Who You Are

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.

Qualifications

• 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

Tools & Technology

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 underwriting portal
• OCR and automated document extraction technology
• AI-assisted underwriting tools designed to enhance submission analysis and underwriting efficiency

What Success Looks Like

Within your first year, you'll:

• Build and manage a profitable Midwest middle market portfolio
• Deliver timely, thoughtful underwriting decisions with strong pricing discipline
• Develop trusted relationships with agency partners
• Successfully partner with Business Development Executives and the MGA Program Director to support agency growth and program success
• Collaborate effectively with Claims and Loss Control on complex risks
• Help improve underwriting workflows and operational efficiency
• Contribute to Insurate's continued growth while maintaining underwriting profitability
• Salary: $115,000–$150,000, commensurate with experience, plus bonus opportunity and equity participation.
• Comprehensive medical, dental, and vision insurance
• 401(k) Plan
• Paid Time Off
• Reimbursement for Internet and phone, up to $150/month
• Equity Participation: Every Insurate employee participates in our equity program, giving you a meaningful stake in the company's long-term success.
• Remote-first work environment that supports flexibility and work-life balance

Location & Travel

• Remote (U.S.)
• Candidates residing in the Midwestern United States are preferred.
• Existing relationships and experience with agencies throughout the Midwest are highly desirable.
• Travel is expected approximately once per quarter for agency visits, team meetings, and company events.

Our Culture

We're a collaborative team that believes great underwriting comes from thoughtful discussion, continuous learning, and shared accountability. We value curiosity, integrity, and sound judgment over bureaucracy, and we encourage our team members to ask questions, challenge assumptions, and contribute ideas that make our business stronger.
As a growing organization, every employee has the opportunity to influence our future. Whether it's improving a process, strengthening an agency relationship, or helping shape our underwriting philosophy, your voice matters here.

Why Insurate?

At Insurate, experienced underwriters do more than evaluate risk—they help shape the future of the business.
Here, you'll have the opportunity to:

• Be trusted to make underwriting decisions—not simply process submissions.
• Collaborate directly with leadership, Business Development Executives, the MGA Program Director, Claims, and Loss Control.
• Help improve underwriting processes rather than work around outdated ones.
• Leverage technology and AI tools that enhance your expertise—not replace it.
• Influence underwriting strategy and operational improvements.
• Participate in our employee equity program and share in the company's long-term success.
• Build meaningful relationships with strategic agency partners while helping grow a profitable portfolio.

Ready to Apply?

If you're looking for an opportunity where your underwriting expertise will have a meaningful impact—and where you'll help shape the future of a growing organization,we'd love to hear from you.