Regional Sales Manager - Remote

Regional Sales Manager

Join a high-performance sales organization where relationship management, strategic execution, and profitability drive success. At Stillwater Insurance Group, our Regional Sales Managers play a critical role in strengthening agency partnerships, expanding market presence, and delivering sustainable, profitable growth within their assigned territories.

Why Stillwater?

Stillwater Insurance Group is a mid-sized national insurance provider offering home, auto, and commercial insurance products across all 50 states. Headquartered in Jacksonville, Florida, with offices in New York and Omaha, we are known for our supportive culture, strong values, and people-first approach.

Our employees consistently describe Stillwater as a company with accessible leadership, collaborative teams, and a genuine commitment to integrity. We emphasize accountability, professional development, and measurable results within a performance-driven environment.

Position Overview

The Regional Sales Manager is responsible for achieving territory financial objectives through effective management of an independent agency force within a defined region. This role executes strategic sales initiatives, develops high-impact agency relationships, and implements tactical business plans to meet production and profitability goals. This position reports to the VP, Sales & Marketing. 

This position operates on a hybrid field schedule:

• One day per week working remotely from home
• Four days per week traveling within the assigned territory for in-person agency meetings

In-person meetings are a core function of the role and represent the majority of weekly activity.

Standard business hours are Monday–Friday, 8:00 a.m. – 5:00 p.m., with flexibility as business needs require.

Territory – Inland Empire, California

This role covers the Inland Empire region, including:

• Riverside County
• San Bernardino County
• Palm Springs
• Palm Desert
• Murrieta
• Temecula

Candidates must reside within the territory. Relocation assistance is not available.

Key Responsibilities

• Identify, evaluate, and appoint agencies that align with Stillwater’s target profile and production expectations
• Develop and execute annual agency production and flow plans
• Establish and maintain strong producer relationships through consistent, in-person engagement
• Create and implement territory-specific tactical sales strategies to achieve financial objectives
• Analyze local market trends, competitive positioning, and growth opportunities
• Maintain comprehensive knowledge of competitor products, pricing, and capabilities
• Lead execution of the Business Development Process and Best Practices
• Collaborate cross-functionally to enhance agency ease-of-use and operational efficiency
• Monitor performance metrics and adjust strategy to ensure achievement of product and profitability goals

Qualifications

Required

• Bachelor’s degree or equivalent experience; or five to ten years of related experience and/or training; or equivalent combination of education and experience
• 6+ years of insurance marketing or sales leadership experience
• Direct home insurance (personal lines property) experience is required
• Strong agency management expertise with demonstrated production growth results
• Financial and business acumen with the ability to analyze territory performance
• Proven ability to build and sustain long-term internal and external relationships
• Strong strategic thinking and market analysis capability
• Excellent verbal, written, presentation, and listening skills
• Strong organizational, analytical, and problem-solving skills
• Ability to manage multiple priorities within a dynamic environment
• Ability to travel extensively within Riverside and San Bernardino Counties

Preferred

• Combined personal and commercial lines experience
• Experience collaborating directly with agency principals and producers
• Demonstrated success executing territory growth strategies 

What You Can Expect

• A performance-driven, results-oriented culture
• Strong executive leadership support
• Opportunities to directly impact territory growth and profitability
• A collaborative environment focused on long-term agency partnerships
• A workplace built on trust, accountability, and integrity

Apply today to advance your sales leadership career with Stillwater Insurance Group.

Employment offers are contingent upon successful completion of a background investigation and pre-employment drug screening. Stillwater Insurance Group is a drug-free workplace and an equal opportunity employer.