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 homeFour 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 – New York and New Jersey

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 expectationsDevelop and execute annual agency production and flow plansEstablish and maintain strong producer relationships through consistent, in-person engagementCreate and implement territory-specific tactical sales strategies to achieve financial objectivesAnalyze local market trends, competitive positioning, and growth opportunitiesMaintain comprehensive knowledge of competitor products, pricing, and capabilitiesLead execution of the Business Development Process and Best PracticesCollaborate cross-functionally to enhance agency ease-of-use and operational efficiencyMonitor 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 experience6+ years of insurance marketing or sales leadership experienceDirect home insurance (personal lines property) experience is requiredStrong agency management expertise with demonstrated production growth resultsFinancial and business acumen with the ability to analyze territory performanceProven ability to build and sustain long-term internal and external relationshipsStrong strategic thinking and market analysis capabilityExcellent verbal, written, presentation, and listening skillsStrong organizational, analytical, and problem-solving skillsAbility to manage multiple priorities within a dynamic environmentAbility to travel extensively within Riverside and San Bernardino Counties

Preferred

Combined personal and commercial lines experienceExperience collaborating directly with agency principals and producersDemonstrated success executing territory growth strategies

What You Can Expect

A performance-driven, results-oriented cultureStrong executive leadership supportOpportunities to directly impact territory growth and profitabilityA collaborative environment focused on long-term agency partnershipsA 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.