Middle Market Underwriting and Sales Region Leader

Westfield; United States; Remote; USD 160,000 - 210,000; Full time

Job summary

Westfield is seeking a Regional Leader for Middle Market Underwriting and Sales to develop and execute underwriting and sales strategy for the assigned U.S. region.

You will lead regional teams, partner with Distribution, Product Management, Marketing, and Underwriting Operations, and drive growth while maintaining underwriting discipline. You will coach and develop leaders, leverage portfolio analytics, and ensure adherence to guidelines and regulatory requirements to deliver profitable results

Qualifications

• 8+ years of Commercial Underwriting experience and 5+ years of direct people management experience.
• Bachelor's degree in related field and/or commensurate work experience.
• Master's degree in a related field is preferred.

Responsibilities

• Leads the regional underwriting and sales organization, establishing priorities and ensuring execution of new business, renewal, pricing, and profitability objectives.
• Develops and mentors regional leaders and teams to strengthen underwriting expertise and collaboration across functions.
• Ensures adherence to underwriting guidelines, authority, policies, regulatory requirements, and QA standards.
• Drives agency and broker engagement, sales presentations, account strategy, and negotiations of coverage and terms.
• Monitors regional financial and operating results; develops action plans to improve performance.
• Allocates resources using portfolio analytics and market insights to identify trends and opportunities.
• Maintains disciplined underwriting authority based on capability and performance.
• Owns talent management for the region, including hiring, succession planning, and development.
• Manages regional expenses and provides forecasts and variance explanations as required.
• Keeps abreast of commercial insurance market conditions and competitor activity to translate insights into regional strategy.

Skills

Leadership

Underwriting

Portfolio management

Sales management

Data analysis

Agency relations

Pricing strategies

Regulatory compliance

Contract management

Team development

Education

Bachelor's degree

Master's degree (preferred)

Tools

CRM software

Data analytics tools

Job description

Job Summary:

The Middle Market Underwriting and Sales Region Leader is accountable for developing and executing the underwriting and sales strategy for an assigned region to achieve profitable growth and targeted financial results. The role leads regional business development, underwriting execution, and portfolio management while partnering with Distribution, Product Management, Marketing, and Underwriting Operations to achieve territory objectives.

The Region Leader provides leadership and direction to the regional team, using market insight, portfolio analytics, and sound underwriting judgment to identify opportunities, address performance issues, and make effective business decisions. The role builds strong agency and broker relationships, drives consistent sales and underwriting practices, and promotes collaboration across field and virtual teams. The Region Leader is also responsible for coaching and developing team members, strengthening underwriting and business development capabilities, and building a high-performing team positioned for sustained success.

Job Responsibilities:

Leads the Middle Market underwriting and sales organization for the region, establishing business priorities, monitoring performance, and ensuring execution of regional new business, renewal, pricing, and profitability objectives.

• Leads underwriting managers and underwriting teams to achieve appropriate productivity, service, and portfolio results while maintaining sound underwriting discipline and effective partnership across Underwriting, Underwriting Practices, and Underwriting Operations.
• Builds a strong culture of collaboration across field, home office, and virtual teams and models effective teamwork, communication, and shared accountability for results.
• Ensures adherence to underwriting guidelines, authority, policies, procedures, regulatory requirements, and quality assurance standards, including timely implementation of corrective actions and QA recommendations.
• Leads and develops other leaders, establishing clear expectations for performance, coaching, and accountability while strengthening the team's underwriting expertise and ability to manage larger and more complex accounts.
• Uses portfolio analytics, market intelligence, and business judgment to identify trends, prioritize opportunities, address performance gaps, allocate resources, and support effective underwriting and business decisions.
• Establishes and maintains a disciplined, objective process for granting and managing underwriting authority based on demonstrated technical capability, experience, judgment, and performance.
• Supports significant new business and renewal opportunities through agency and broker engagement, sales presentations, account strategy, and negotiation of coverage, pricing, financial terms, and service solutions.
• Monitors performance against regional financial and operating objectives, identifies emerging issues and opportunities, and develops action plans to improve new business production, retention, pricing, profitability, and overall portfolio performance.
• Owns talent management for the region, including hiring and selection, succession planning, performance and compensation management, employee development, career coaching, workload management, and resolution of employee issues that may affect team effectiveness.
• Manages regional expenses within established plans, monitors spending throughout the year, and provides forecasts and variance explanations as required.
• Maintains a strong understanding of commercial insurance market conditions, competitor activity, industry trends, and jurisdictional developments through agency engagement, industry participation, and other sources, and translates those insights into regional underwriting and sales strategies.

Job Qualifications:

• 8+ years of Commercial Underwriting experience and 5+ years of direct people management experience.
• Bachelor's degree in related field and/or commensurate work experience.
• Master's degree in a related field is preferred.

Location:

• Remote territories AZ/CO/FL/GA/MN/IA/TN/KY or Headquarters.

Licenses and Certifications (Possesses one or more of the following):

• Chartered Property Casualty Underwriter (CPCU) (preferred)
• Associate in Commercial Underwriting (AU) (preferred)
• Certified Insurance Counselor

• Certified Risk ManagerBehavioral Competencies:Collaboration Communicates Effectively
• Customer Focus
• Decision Quality
• Nimble Learning
• Builds Effective Teams
• Business Insight
• Develops talent
• Directs Work
• Ensures Accountability
• Manages Complexity
• Drives Vision & Purpose
• Strategic Mindset

Technical Skills:

• Commercial Lines Underwriting
• Underwriting Strategy
• Business Development and Sales Management
• Data Analysis & Reporting
• Agency Management
• Pricing Analytics
• Contract Management
• Predictive Modeling
• Customer Relationship Management
• Regulatory Compliance
• Financial ManagementThis job description describes the general nature and level of work performed in this role. It is not intended to be an exhaustive list of all duties, skills, responsibilities, knowledge, etc. These may be subject to change and additional functions may be assigned as needed by management.