Territory Outside Sales Pro | Flexible Hours & Growth

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

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.