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Nautilus Insurance Company

Regional Underwriting Director - Midwest

Company : Nautilus Insurance Company

Location : Chicago, IL, 60661

Job Type : Full Time / Part Time

Date Posted : 4 January 2026

Company Details

Berkley Fire & Marine Underwriters was launched in 2013 and is a W. R. Berkley operating unit offering preferred inland marine and related property risks and services. Headquartered in Chicago, Berkley Fire & Marine Underwriters serves customers throughout the United States, both regionally and nationwide.  With the ability to craft customized terms, we provide the most effective protection for those in the construction, logistics, manufacturing and transportation industries.

The Company is an equal employment opportunity employer. 

Responsibilities

As a Regional Underwriting Director, Midwest Region, Inland Marine, you will provide thought leadership on a continual basis to always be improving underwriting acumen and standards as needed and will pro-actively adjust to market and changing dynamics. You'll maintain Berkley Fire & Marine underwriting standards while supporting the business strategy initiatives and financial return goals through underwriting excellence. Your extensive and diversified technical property and inland marine underwriting expertise will be utilized to evaluate risks in a referral capacity. The role will also support underwriting projects including inland marine product, guidance, tools and continual underwriting education. As the Regional Underwriting Director, you will also be responsible for training & development of the technical acumen, compliance and underwriting standards of our underwriting teams along with the RVP. 

What you can expect:

  • Culture of innovation, teamwork, supportive colleagues and leaders willing to invest in talent
  • Internal mobility opportunities 
  • Visibility to senior leaders and partnership with cross functional teams
  • Opportunity to impact change
  • Benefits – competitive compensation, paid time off, comprehensive wellness benefits and programs, employer funded health savings account, profit sharing, 401k, paid parental leave, employee stock purchase plan, tuition assistance and professional continuing education

We'll count on you to:

  • Provide feedback on coaching opportunities and develop related training as needed.
  • Collaborate with RVP(s) as needed to support risk quality & decision-making feedback and opportunities for individual improvement and coaching.
  • Deliver timely feedback to underwriting and leadership outlining areas for improvement.
  • Act as a resource for underwriting and support local teams with training for best practices and collaborative conversation related to underwriting improvement.
  • Continuously look for ways to improve underwriting standards. Shares value-added recommendations with Senior Management.
  • Maintain a strong pulse on the underwriting environment, market conditions, competition and other factors facing the industry.
  • Collaborate to develop products and tools.
  • Work with product to manage and maintain usage of manuscripts in compliance with regulatory needs and BFM directives.
  • Work with compliance to manage and maintain usage of filings, products, etc.
  • Work with Berkley Fire & Marine and Berkley Shared Services underwriting resources in support of project initiatives.
  • Act as a resource for the underwriting office for future platform integration such as Guidewire.
  • Other underwriting related projects as assigned.

Qualifications

What you need to have:

  • Bachelor’s Degree in relevant discipline or equivalent combination of education and experience.
  • 10+ years of Insurance Industry experience.
  • Expertise in Inland marine lines of coverage
  • Seasoned commercial property & inland marine underwriting expertise:
    • prior experience as an underwriter.
    • experience with underwriting best practices development and monitoring.
    • exposure to risk evaluation through referrals and/or in a leadership capacity.
    • knowledgeable about pricing evaluation, forms and coverage and regulatory compliance.
    • understanding and knowledge of treaty and facultative reinsurance structures.
  • Strong Project Management skills and experience.
  • Experience with direct or indirect coaching and development of people.
  • Advanced-level knowledge of insurance products/coverage, market segments and marketplace.
  • Must have strong interpersonal skills, business acumen, and sound business judgment and be capable of effectively communicating with a diverse range of individuals and teams.
  • Advanced knowledge of Microsoft office suite including excel, power point and Word.
  • Demonstrates ability to lead people and influence others to achieve results.
  • Must be action oriented and have strong drive to achieve results.
  • Ability to thrive in a fast-paced environment that continuously adapts based on customer needs and industry trends.
  • Strong aptitude for analyzing and translating data in actionable steps that result in expected outcomes.
  • Ability to consistently demonstrate the WRBC Leadership Core Competencies, Innovation Behaviors, and Berkley Fire & Marine Core Competencies and Values.

Additional Company Details

We do not accept any unsolicited resumes from external recruiting agencies or firms. The company offers a competitive compensation plan and robust benefits package for full time regular employees which for this role include: • Base Salary Range: $96,800 - $176,000 • Eligible to participate in annual discretionary bonus. • Benefits: Health, Dental, Vision, Life, Disability, Wellness, Paid Time Off, 401(k) and Profit-Sharing plans. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment.

Sponsorship Details

Sponsorship not Offered for this Role

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Frequently asked questions

A Regional Underwriting Director in the Midwest focuses on inland marine and commercial property risks unique to that region’s industries, such as construction and transportation. They balance local market dynamics with corporate underwriting standards, ensuring tailored risk evaluation and strategic leadership distinct from broader or national underwriting positions.

Proficiency in inland marine coverage combined with deep knowledge of Midwest market conditions is critical. They excel in coaching underwriting teams, adapting to regulatory changes, and developing innovative tools, leveraging regional insights to optimize risk management and maintain competitive underwriting standards.

Advancement often leads to senior executive roles in underwriting or risk management, especially within specialized areas like inland marine or commercial property. Opportunities may expand into national leadership or cross-functional positions due to the strategic insights gained from managing diverse teams and complex regional portfolios.

While not mandatory, credentials like CPCU (Chartered Property Casualty Underwriter) or ARM (Associate in Risk Management) are highly regarded in Chicago’s insurance market. These certifications demonstrate advanced knowledge valued by employers like Nautilus Insurance Company and support compliance with regional regulatory frameworks.

Chicago, as a major insurance hub, maintains robust demand for senior underwriting leadership, driven by its concentration of logistics and manufacturing sectors. Compared to smaller Midwest cities, roles here tend to offer greater complexity, higher salaries, and more opportunities for strategic impact within regional underwriting teams.

Nautilus emphasizes innovation, teamwork, and continuous learning, which means their Regional Underwriting Directors are expected to lead proactive underwriting improvements, collaborate across departments, and mentor teams. This culture fosters a dynamic environment where leaders shape both underwriting standards and business strategy.

Navigating diverse inland marine risks while aligning with Berkley Fire & Marine’s underwriting standards presents complexities. Additionally, balancing project management, regulatory compliance, and coaching responsibilities amid evolving market conditions requires adaptability and strategic foresight specific to Nautilus’ operational model.

Compensation typically ranges from $96,800 to $176,000 annually, reflecting experience, skills, and role complexity. This aligns with competitive market rates for senior underwriting directors in Chicago, factoring in the region’s cost of living and Nautilus’ comprehensive benefits and bonus structures.

Extensive understanding of Midwest market trends, local industry risks, and regulatory nuances is vital. It enables underwriting directors to tailor risk assessments effectively, engage with regional teams meaningfully, and maintain competitive pricing and compliance, which are essential for sustained underwriting excellence.

Beyond assessing risks, duties include mentoring underwriting teams, developing training programs, collaborating on product development, managing compliance processes, and leading strategic initiatives to continually elevate underwriting standards and align with company-wide financial goals.

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