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Small Business Territory Leader (Western Zone)

August 5, 2026

Job Description Job Summary: The Territory Leader (Western Zone) is responsible for driving profitable small business growth across a multi-state territory (AZ,NM,CO,IL,WI,MN), supporting both field and a national virtual 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 <ul><li>Translate the Small Business strategy into clear regional priorities, sales plans, and execution rhythms. </li><li>Drive disciplined sales management practices, including goal setting, forecasting, pipeline management, and performance reviews. </li><li>Lead regional execution of segmentation, agency engagement strategy, and growth initiatives.</li></ul> People Leadership & Talent Development <ul><li>Lead, coach, and develop Territory Managers supporting the assigned territory. </li><li>Own hiring, onboarding, performance management, and succession planning for the zone.</li><li>Build a strong performance culture grounded in accountability, coaching, and continuous improvement. </li></ul> Agency & Market Engagement <ul><li>Serve as a senior sales presence with key agency partners across the assigned territory, including joint planning, escalations, and growth discussions. </li><li>Ensure a consistent agency experience across field and virtual sales engagement models. </li><li>Monitor market trends, competitive dynamics, and agency needs to inform regional strategy and priorities.</li></ul> Cross-Functional Partnership <ul><li>Partner closely with Underwriting, Product, Distribution, and other business units to ensure alignment and execution. </li><li>Proactively identify process or capability gaps impacting sales performance and drive solutions. </li><li>Support change initiatives and operational improvements that enhance agent experience and sales productivity.</li></ul> Execution & Governance <ul><li>Establish clear operating rhythms for the region, including monthly reviews, performance tracking, and action planning. </li><li>Use data and insights to identify trends, risks, and opportunities, adjusting strategy as needed. </li><li>Manage priorities, remove barriers, and ensure focus on the highest-impact activities.</li></ul> Qualifications: <ul><li>8+ years of progressive experience in insurance sales, sales leadership, or business development. </li><li>Demonstrated success leading sales teams across multi-state or complex territories. </li><li>Strong understanding of small business insurance distribution and agency dynamics. </li><li>Proven ability to drive profitable growth.</li><li>Bachelor's degree in Business, Marketing, or related field, or equivalent experience. </li><li>Valid driver's license and ability to travel regularly within the assigned territory.</li></ul> Core Competencies: <ul><li>Sales Leadership & Execution </li><li>Business & Market Insight </li><li>People Development & Coaching </li><li>Strategic Planning & Prioritization </li><li>Accountability & Performance Management </li><li>Cross-Functional Collaboration </li><li>Change Leadership </li><li>Data-Driven Decision Making</li></ul> Additional Information <ul><li>Role includes a company car with regular travel within the assigned territory.</li></ul> 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. About Us 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.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...