Outside Sales Representative

Heritage Insurance is looking for driven, ambitious, and people-focused individuals to join our growing team as Outside Sales Representatives .

If you're ready to leverage your sales skills in a career where your effort is rewarded, your growth is supported, and the work you do can make a meaningful difference for families and businesses, this could be the opportunity you've been looking for.

Heritage Insurance provides reliable insurance solutions designed to help protect what matters most. As an Outside Sales Representative, you'll work directly with small and medium-sized business owners and decision-makers , helping them understand their insurance options while developing your own territory and building a long-term book of business.

Competitive Earning Potential with weekly draw pay, commissions, and bonuses

Commission Eligibility Upon Start

Flexible Scheduling with the ability to manage your own working hours

Assigned Sales Territory

Comprehensive Training through virtual classroom and hands-on field training

Dedicated Sales Training and Mentorship

Quarterly and Annual Incentive Trips

Cash Bonus Opportunities

Stock Share Opportunities

Career Advancement based on personal performance

Ongoing Professional Development

Advanced Sales and Leadership Training

Optional Travel Opportunities to work alongside sales teams in other territories

As an Outside Sales Representative , you'll primarily work within your assigned territory, meeting face-to-face with business owners and decision-makers.

You'll introduce businesses and their employees to supplemental insurance products and solutions , identify their needs, and build lasting professional relationships.

Your responsibilities will include:

Meet face-to-face with small and medium-sized business owners and decision-makers

Present supplemental insurance products and solutions based on client needs

Prospect for new business through local businesses, referrals, and existing relationships

Develop and manage your assigned sales territory

Build and maintain your own book of business

Follow up with prospective and current clients

Respond to client emails and phone calls

Schedule appointments to review client needs and coverage

Re-service existing clients and identify additional opportunities

Participate in scheduled team meetings, training sessions, and manager calls

Establish and submit your weekly working schedule to your sales manager

Maintain consistent prospecting and sales activity

Track and submit daily sales metrics and activity

We're willing to train the right candidate. Our training program combines virtual classroom instruction with hands-on sales training in your assigned territory .

You'll receive training and support in:

Outside and B2B sales

Prospecting and territory development

Needs-based selling

Insurance product presentations

Building relationships with business owners

Overcoming objections

Handling rejection

Follow-up and client retention

Building and managing a book of business

Time and activity management

Sales performance strategies

You'll also have access to ongoing professional development, advanced sales training, and leadership development as you grow within the organization.

We're looking for individuals who are motivated by achievement and excited about building a career based on their own performance.

The ideal candidate is:

Positive, energetic, and professional

Driven and goal-oriented

Confident communicating with business owners and decision-makers

An excellent written and verbal communicator

Empathetic and able to connect with people

Resilient and comfortable handling rejection

Confident overcoming objections

Self-motivated and disciplined

Able to work independently and manage their time effectively

Coachable and committed to continuous improvement

Competitive and motivated to exceed expectations

Accountable for their activity and results

Passionate about helping others

This opportunity can be a great fit for candidates with experience in:

Outside sales

Field sales

B2B sales

Territory sales

Business development

Account management

Insurance sales

Recruiting

Customer service

Retail sales

Call center sales

Door-to-door sales

If you've developed strong sales skills but have outgrown call centers, retail, or traditional sales roles , Heritage Insurance offers an opportunity to build greater independence, increase your earning potential, and develop a long-term career.

Job Type: Full-Time Estimated Annual Earnings: $76,000–$100,000+ Schedule: Flexible, 8-hour shift Work Setting: Outside Sales / Field Sales / Territory Sales Sales Type: Business-to-Business (B2B) Industry: Insurance / Supplemental Insurance

If you're ready for a sales career where your effort, consistency, and performance can directly influence your success , Heritage Insurance wants to hear from you.

We're committed to helping individuals develop the skills, confidence, and leadership abilities needed to build a successful career in insurance sales.

Learn more about Heritage Insurance and our commitment to providing reliable protection for American families at Heritage Insurance .