B2B Outside Sales Pro - Flexible Hours, Leadership Path

R.I.S.E. Financial; Newberg (OR); On-site; USD 75,000 - 100,000; Full time

Benefits offered by this job

Bonuses & incentives

Training & development

Flexibility

Leadership opportunities

Job summary

R.I.S.E. Financial is seeking Outside Sales Representatives for a dynamic, in-person B2B sales role. You will engage business owners and managers in your territory, offering top-tier supplemental insurance products to enhance financial security for their employees and families.

You’ll control your schedule, build a personal book of business, and participate in hands-on training and mentorship. The position offers a generous pay mix plus incentives and a fast path to leadership roles.

Qualifications

• Licensed in Health & Life general lines or willing to obtain the license (we cover fees).
• Bachelor's degree or 4+ years of professional (post-high school) work experience.

Responsibilities

• Work in your assigned territory, meeting business owners and employees to offer supplemental insurance.
• Build and maintain your own book of business with cold calling and follow-up appointments.
• Lead product presentations, one-on-one and for groups of 50–100+ people.
• Set your own schedule, track activities, and hit monthly/quarterly sales goals.
• Receive and follow up on leads, attend sales meetings, and report daily metrics.
• Grow professionally with ongoing training in advanced sales and leadership.

Skills

Driven and self-motivated

Relationship builder

Competitive and resilient

Goal-oriented

Passionate

Education

Bachelor's degree or 4+ years work experience

Job description

R.I.S.E. Financial is seeking Outside Sales Representatives for a dynamic, in-person B2B sales role. You will engage business owners and managers in your territory, offering top-tier supplemental insurance products to enhance financial security for their employees and families.

You’ll control your schedule, build a personal book of business, and participate in hands-on training and mentorship. The position offers a generous pay mix plus incentives and a fast path to leadership roles.