Small Business Territory Leader (Eastern Zone)

Job Summary:

The Territory Leader (Eastern Zone) is responsible for driving profitable small business growth across a multi-state territory (FL, GA, TN, MD, VA, PA, NC, SC.), supporting the field sales model. This role provides leadership to sales teams operating within the assigned zone and ensures disciplined execution of Westfield’s Small Business strategy while delivering strong production and profitability results.

The Territory Leader serves as the primary sales leader for the zone, accountable for sales performance, talent development, agency engagement, and cross-functional alignment. This role plays a critical part in executing national and regional growth initiatives while building a high-performing, accountable sales culture.

Key Responsibilities:

Sales & Growth Leadership

• Translate the Small Business strategy into clear regional priorities, sales plans, and execution rhythms.
• Drive disciplined sales management practices, including goal setting, forecasting, pipeline management, and performance reviews.
• Lead regional execution of segmentation, agency engagement strategy, and growth initiatives.

People Leadership & Talent Development

• Lead, coach, and develop Territory Managers supporting the assigned territory.
• Own hiring, onboarding, performance management, and succession planning for the zone.
• Build a strong performance culture grounded in accountability, coaching, and continuous improvement.

Agency & Market Engagement

• Serve as a senior sales presence with key agency partners across the assigned territory, including joint planning, escalations, and growth discussions.
• Ensure a consistent agency experience across field and virtual sales engagement models.
• Monitor market trends, competitive dynamics, and agency needs to inform regional strategy and priorities.

Cross-Functional Partnership

• Partner closely with Underwriting, Product, Distribution, and other business units to ensure alignment and execution.
• Proactively identify process or capability gaps impacting sales performance and drive solutions.
• Support change initiatives and operational improvements that enhance agent experience and sales productivity.

Execution & Governance

• Establish clear operating rhythms for the region, including monthly reviews, performance tracking, and action planning.
• Use data and insights to identify trends, risks, and opportunities, adjusting strategy as needed.
• Manage priorities, remove barriers, and ensure focus on the highest-impact activities.

Qualifications:

• 8+ years of progressive experience in insurance sales, sales leadership, or business development.
• Demonstrated success leading sales teams across multi-state or complex territories.
• Strong understanding of small business insurance distribution and agency dynamics.
• Proven ability to drive profitable growth.
• Bachelor’s degree in Business, Marketing, or related field, or equivalent experience.

• Valid driver’s license and ability to travel regularly within the assigned territory.

Location:

Territory: FL, GA, TN, MD, VA, PA, NC, SC

Core Competencies:

• Sales Leadership & Execution
• Business & Market Insight
• People Development & Coaching
• Strategic Planning & Prioritization
• Accountability & Performance Management
• Cross-Functional Collaboration
• Change Leadership

• Data-Driven Decision Making

Additional Information

• Role includes a company car with regular travel within the assigned territory.

This 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.

Founded in 1848, Westfield is a global leader in property and casualty insurance, delivering superior risk insights and innovative solutions to customers through a diverse portfolio of insurance products. Westfield underwrites commercial, personal, surety, and specialty lines of coverage through a network of leading independent agents and brokers in the United States and specialty products through Lloyd’s of London Syndicate 1200. As a mutual insurance company with more than 3,000 employees, Westfield has revenues in excess of $4 billion and more than $10 billion in assets.