Outside Sales Representative

True North Group LLC.; Bend (OR); On-site; USD 50,000 - 80,000; Full time

Benefits offered by this job

Comprehensive training

Weekly draw pay

Bonuses and commissions

Stock awards

Career growth

Flexible schedule

Job summary

True North Group is an insurance agency helping small and mid-sized businesses. We are hiring an Outside Sales Representative in Bend, Oregon to visit local companies, uncover risk needs, and tailor benefit packages.

You will be a trusted advisor who supports clients through claims and questions. You’ll balance in-person visits with strategic outreach, manage your pipeline in Salesforce, and pursue ambitious sales goals while delivering exceptional service.

Qualifications

• Bachelor's degree or 4+ years in a customer-facing role.
• Comfort with technology; Salesforce experience is a plus.
• Coachable attitude and drive to exceed goals.

Responsibilities

• Prospect & Connect: Identify local businesses, connect with the community, and schedule discovery meetings.
• Present Solutions: Lead tailored benefits presentations for business owners and employee groups.
• Maintain Relationships: Respond promptly to calls and emails, manage renewals, and assist clients through claims.
• Track Your Pipeline: Use Salesforce to log interactions, manage tasks, and measure progress.
• Collaborate with Your Team: Join weekly strategy sessions to share best practices and celebrate wins.
• Set Your Own Hours: Build a schedule that fits the businesses you serve—early mornings, late afternoons, or midday visits.

Skills

Relationship building

Self-starter

Clear communication

Organized & tech-savvy

Service oriented

Licensed or license-ready

Education

Bachelor's degree or 4 years customer-facing experience

Tools

Salesforce

Job description

Join Our Team at True North Group

Position: Outside Sales Representative

Number of Openings: 1 Territory Role Available

About True North Group

At True North Group, we're more than an insurance agency—we're trusted partners to small and mid-sized businesses. Our mission is to protect what matters most: their people. We do this by delivering personalized supplemental insurance solutions and exceptional service. If you're someone who thrives on building relationships and helping others, this Outside Sales Representative role was made for you.

The Role

As an Outside Sales Representative, you'll be on the front lines of our business, visiting local companies in your assigned territory. You'll discover each client's unique needs, guide them through our range of insurance products, and become a trusted advisor they can rely on. With the freedom to set your own schedule, you'll balance in-person visits with strategic phone outreach, all supported by our intuitive Salesforce CRM.

What We're Looking For

• Relationship-Builder: You're energized by meeting new people and earning their trust.
• Self-Starter: You manage your own calendar, follow through on leads, and set ambitious goals.
• Clear Communicator: You explain complex information simply—whether one-on-one or presenting to groups of up to 75.
• Organized & Tech-Savvy: You keep detailed records in Salesforce and never let a follow-up slip through the cracks.
• Service-Oriented: You genuinely care about clients' well-being, guiding them through claims and policy questions with empathy.
• Licensed or Ready: You hold (or will obtain within 90 days) a Health & Life general lines license—we reimburse the fees and support your preparation.

Position Overview

In this outside sales position, you will:

• Prospect & Connect: Identify local businesses, connect with the community, and schedule discovery meetings.
• Present Solutions: Lead tailored benefits presentations for business owners and employee groups.
• Maintain Relationships: Respond promptly to calls and emails, manage renewals, and assist clients through claims.
• Track Your Pipeline: Use Salesforce to log interactions, manage tasks, and measure your progress.
• Collaborate with Your Team: Join weekly strategy sessions to share best practices and celebrate wins.
• Set Your Own Hours: Build a schedule that fits the businesses you serve—early mornings, late afternoons, or midday visits.

We Offer

• Comprehensive Training: Blend of virtual workshops and ride-along field sessions to get you client-ready.
• Weekly Draw Pay: Steady income floor plus immediate eligibility for bonuses and commissions.
• Incentive Rewards: Quarterly retreats, annual trips, cash bonuses, stock awards, and lifetime-vested renewal commissions.
• Career Growth: Clear pathways to senior sales roles, field training positions, or agency leadership.
• Supportive Culture: A team that shares resources, mentors new reps, and celebrates collective success.
• Flexible Schedule: More autonomy over your hours as you build your client base.

Additional Qualifications

• Bachelor's degree or a minimum of 4 years in a customer-facing role—recent graduateswelcome.
• Comfort with technology—Salesforce experience is a plus.
• Coachable attitude and a drive to exceed goals.

Your New Journey Starts Here

If you're ready to hit the ground running, forge meaningful client relationships, and grow a rewarding career in outside sales, True North Group is here to support you every step of the way.