Outside Sales Representative

Build Your Career. Build Your Territory. Protect What Matters Most.

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.

Estimated Annual Earnings: $76,000–$100,000+

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.

Why Join Heritage Insurance?

• 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

The Opportunity

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

Comprehensive Training & Support

Previous insurance sales experience is preferred, but it's not required.

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.

What We're Looking For

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

Sales Experience Is Preferred — But Not Required

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.

Licensing & Education Requirements

• Active Health & Life General Lines license, or willingness and ability to obtain a Health & Life Producer License

• Licensing reimbursement available

• Bachelor's degree OR a minimum of 4 years of professional post-high-school work experience

• Candidates within 6 months of completing their degree may be considered

• Candidates with less than 4 years of professional experience may be considered if they have relevant or specialized outside sales experience

Position Details

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

Build Your Territory. Grow Your Income. Make an Impact.

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.

Apply today and take the next step toward building your future with Heritage Insurance.