Regional Sales Manager - Remote

Stillwater Insurance Group

1d•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

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

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