Insurance Sales Representative Jobs in Oregon
Insurance Sales Representative jobs in Oregon are in steady demand, with hiring concentrated in personal lines, commercial property, and health and benefits coverage across the state's financial services and healthcare sectors. Portland, Salem, and Eugene lead in openings, and established employers such as Regence BlueCross BlueShield, Farmers Insurance, and State Farm maintain consistent hiring for agents at every level from entry-level producers to senior account managers. The most in-demand specialties include life and health insurance, commercial lines, and Medicare supplement products. See the openings below and apply to the ones that match your experience.
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Showing 5 of 22+ Insurance Sales Representative jobs
Insurance Sales Representative and Trainer
Company: Canyon Creek Financial
Employment Type: Full-Time | Outside Sales | B2B Sales
Location: In-person, local territory (with occasional travel)
Schedule: MondayFriday (with flexibility, occasional weekends as needed)
Compensation: Weekly Base Draw, Uncapped Commissions, Bonuses | $80,000$100,000 annually | Licensing Reimbursement, Training
Lead, Sell, and Inspire at Canyon Creek Financial
At Canyon Creek Financial, we believe success is built by people who take initiative, act with purpose, and aren't afraid to lead from the front.
We're looking for a Supplemental Insurance Sales Representative and Trainer who thrives on challenge, values independence, and is motivated by both personal achievement and the growth of others. In this role, you'll have the opportunity to build meaningful client relationships, guide new team members, and step into a clear leadership pathway.
What You'll Do
Lead B2B Sales Efforts Conduct in-person outreach with business owners and professionals to deliver supplemental insurance solutions
Train and Mentor New Agents Provide guidance and support to teammates in the field, helping them grow in skill and confidence
Own Your Success Manage your own schedule, territory, and income with autonomy and accountability
Build Relationships Establish long-term trust with clients and colleagues through consistent follow-up and service
What Sets This Role Apart
Reliable and Unlimited Pay Weekly base draw plus uncapped commissions and bonuses
Licensing Support and Reimbursement State fees covered to help you get licensed quickly
Leadership Pathway Opportunities to step into team leadership and training roles
Autonomy and Flexibility Control your time, goals, and growth
High-Impact Work Protect families and businesses while building your own legacy
Qualifications
Proven B2B Sales Experience At least 1 year with measurable success
Mentorship or Coaching Background (Preferred) Experience guiding or supporting others a plus
Exceptional Communication Skills Confident and clear in both in-person and written communication
Leadership-Driven Motivated to inspire and support others while achieving personal goals
Organized and Self-Motivated Strong time and task management skills with minimal supervision
Relationship-Oriented Committed to building trust and long-term connections
Resilient and Positive Maintains a solutions-first mindset in the face of challenges
Additional Requirements
Valid driver's license and reliable transportation for local travel
Occasional overnight travel within territory
Access to a smartphone, iPad, and data plan
Willingness to obtain a state Health license (not required to apply)
Compensation and Benefits
Earnings: $80,000$100,000 annually, depending on performance
Pay Structure: Weekly base draw, commissions, and bonuses from day one
Employment Type: Full-Time Independent Contractor | Outside Sales | B2B Sales
Incentives: Quarterly/annual bonuses, incentive trips, stock options
Sales Cycle: Short cycle (typical decisions within 3 business days)
Support Provided: CRM access, structured training, mentorship, licensing reimbursement
Grow with Purpose. Lead with Confidence.
If you're ready to take control of your success, build meaningful client relationships, and guide others toward achievement, this role offers the platform to lead, sell, and inspire.
Apply today and take your next step into leadership with Canyon Creek Financial.
Learn more at: www.canyoncreekfinancial.com
Insurance Sales Representative and Trainer
Company: Canyon Creek Financial
Employment Type: Full-Time | Outside Sales | B2B Sales
Location: In-person, local territory (with occasional travel)
Schedule: MondayFriday (with flexibility, occasional weekends as needed)
Compensation: Weekly Base Draw, Uncapped Commissions, Bonuses | $80,000$100,000 annually | Licensing Reimbursement, Training
Lead, Sell, and Inspire at Canyon Creek Financial
At Canyon Creek Financial, we believe success is built by people who take initiative, act with purpose, and aren't afraid to lead from the front.
We're looking for a Supplemental Insurance Sales Representative and Trainer who thrives on challenge, values independence, and is motivated by both personal achievement and the growth of others. In this role, you'll have the opportunity to build meaningful client relationships, guide new team members, and step into a clear leadership pathway.
What You'll Do
Lead B2B Sales Efforts Conduct in-person outreach with business owners and professionals to deliver supplemental insurance solutions
Train and Mentor New Agents Provide guidance and support to teammates in the field, helping them grow in skill and confidence
Own Your Success Manage your own schedule, territory, and income with autonomy and accountability
Build Relationships Establish long-term trust with clients and colleagues through consistent follow-up and service
What Sets This Role Apart
Reliable and Unlimited Pay Weekly base draw plus uncapped commissions and bonuses
Licensing Support and Reimbursement State fees covered to help you get licensed quickly
Leadership Pathway Opportunities to step into team leadership and training roles
Autonomy and Flexibility Control your time, goals, and growth
High-Impact Work Protect families and businesses while building your own legacy
Qualifications
Proven B2B Sales Experience At least 1 year with measurable success
Mentorship or Coaching Background (Preferred) Experience guiding or supporting others a plus
Exceptional Communication Skills Confident and clear in both in-person and written communication
Leadership-Driven Motivated to inspire and support others while achieving personal goals
Organized and Self-Motivated Strong time and task management skills with minimal supervision
Relationship-Oriented Committed to building trust and long-term connections
Resilient and Positive Maintains a solutions-first mindset in the face of challenges
Additional Requirements
Valid driver's license and reliable transportation for local travel
Occasional overnight travel within territory
Access to a smartphone, iPad, and data plan
Willingness to obtain a state Health license (not required to apply)
Compensation and Benefits
Earnings: $80,000$100,000 annually, depending on performance
Pay Structure: Weekly base draw, commissions, and bonuses from day one
Employment Type: Full-Time Independent Contractor | Outside Sales | B2B Sales
Incentives: Quarterly/annual bonuses, incentive trips, stock options
Sales Cycle: Short cycle (typical decisions within 3 business days)
Support Provided: CRM access, structured training, mentorship, licensing reimbursement
Grow with Purpose. Lead with Confidence.
If you're ready to take control of your success, build meaningful client relationships, and guide others toward achievement, this role offers the platform to lead, sell, and inspire.
Apply today and take your next step into leadership with Canyon Creek Financial.
Learn more at: www.canyoncreekfinancial.com
See All 22 Insurance Sales Representative Jobs in Oregon
Find roles in Oregon that match your experience and apply in just a few clicks.
Find JobsInsurance Sales Representative Jobs by City in Oregon
Where Oregon roles are concentrated, by current openings.
Insurance Sales Representative Job Market in Oregon
A snapshot from current Oregon openings, updated as new roles post.
Who's Hiring
Top Industries Hiring
- Insurance
What Oregon Employers Look For
The qualifications that appear most often in insurance sales representative jobs across Oregon.
- Active Oregon Department of Financial Regulation Property and Casualty or Life and Health license
- Proven ability to meet or exceed individual sales targets in a commission-based environment
- Strong customer service skills with experience managing a personal or commercial book of business
- Familiarity with comparative rater tools, agency management systems, or carrier quoting platforms
- Valid driver's license and reliable transportation for client appointments or territory coverage
- Bachelor's degree in business, finance, or a related field, or equivalent sales experience
Insurance Sales Representative Jobs in Oregon: Frequently Asked Questions
How do you become a insurance sales representative in Oregon?
To become an insurance sales representative in Oregon, you must obtain a license through the Oregon Department of Financial Regulation. The path starts with completing a state-approved pre-licensing education course for your chosen line of authority, such as Property and Casualty or Life and Health, then passing the corresponding Oregon licensing exam administered by Pearson VUE. No college degree is required to sit for the exam, though most employers prefer some post-secondary education or prior sales experience.
Which companies hire insurance sales representatives in Oregon?
Employers hiring insurance sales representatives in Oregon right now include State Farm, Canyon Creek Financial, and Farmers Insurance, based on current listings on Migrate Mate as of November 2026. Oregon's large regional health insurers and national carriers with strong Pacific Northwest footprints tend to post the most consistent openings year-round.
Which Oregon cities have the most insurance sales representative jobs?
Portland, Bend, and Eugene have the most insurance sales representative openings in Oregon. Portland's concentration of corporate headquarters, regional carrier offices, and independent agencies drives the bulk of listings, while Salem's role as the state capital brings demand from public employee benefit programs, and Eugene's growing population and small-business community supports a steady need for personal and commercial lines agents.
Are there remote insurance sales representative jobs in Oregon?
Yes, though they are less common than in purely desk-based fields, since many insurance sales roles involve in-person client meetings and local territory work. About 33% of insurance sales representative openings tied to Oregon are remote or hybrid as of November 2026, with the remote share concentrated in inside sales, telephone-based Medicare or supplemental health enrollment, and commercial account servicing roles that rely on digital communication rather than field visits.
How can I get hired as a insurance sales representative in Oregon with little or no experience?
The most realistic entry path is obtaining your Oregon insurance license first, which signals commitment and lets you start in a licensed role immediately. Large regional employers such as Regence BlueCross BlueShield and national carriers with Portland-area offices regularly bring on entry-level sales agents for inside sales or Medicare enrollment roles that require a license but not a prior book of business. Adjacent starting points include customer service representative, insurance assistant, or claims processor roles at Oregon agencies, which often sponsor your licensing and move you into a producer role within a year.
Where can I find and apply to insurance sales representative jobs in Oregon?
You can find and apply to insurance sales representative jobs in Oregon on Migrate Mate, which lists current Oregon openings from carriers, agencies, and brokerages. Search by city or specialty to narrow results to the roles that fit your license type and experience level, then apply directly to the ones that match.
See All 22 Insurance Sales Representative Jobs in Oregon
Find roles in Oregon that match your experience and apply in just a few clicks.
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