Outside Sales Representative & Trainer

Canyon Creek Financial LLC.; Hillsboro (OR); On-site; USD 80,000 - 100,000; Full time

Benefits offered by this job

Licensing reimbursement

Training

Bonuses

Stock options

Trips

Job summary

Canyon Creek Financial is seeking an Outside Sales Representative & Trainer to operate in-person within the local territory, with occasional travel. You will drive B2B sales, build relationships with business owners, and mentor new agents through hands-on coaching while advancing leadership skills.

The role offers a weekly base draw plus uncapped commissions and bonuses, with licensing reimbursement and structured training to support growth and success.

Qualifications

• At least 1 year of B2B sales experience.
• Strong communication and presentation skills.
• Ability to coach and mentor others in the field.
• Organized, self-driven, and able to manage territory.

Responsibilities

• Drive B2B sales by building relationships with business owners and delivering tailored insurance solutions.
• Train and mentor new agents with patience and structure in the field.
• Own your schedule, territory, and income while maintaining accountability.

Skills

B2B sales

Communication

Coaching

Time management

Tools

CRM

Job description

Outside Sales Representative & Trainer

Company: Canyon Creek Financial
Type: Full-Time | Outside Sales | B2B Sales
Location: In-person, local territory (occasional travel)
Schedule: Monday–Friday (with flexibility, occasional weekends)
Compensation: Weekly Base Draw + Uncapped Commissions + Bonuses | $80,000–$100,000+ annually | Licensing Reimbursement, Training & Incentives

Empower. Guide. Grow.

At Canyon Creek Financial, we know success comes from more than just hitting numbers—it's about staying focused, persevering through challenges, and helping others rise alongside you.

We're seeking a Supplemental Insurance Sales Representative and Trainer who not only thrives in direct sales but also has a true passion for facilitation, coaching, and guiding others. In this role as an independent contractor, you'll connect with business owners, provide valuable insurance solutions, and mentor new agents—helping them find their footing while sharpening your own leadership skills.

What You'll Do

• Drive B2B Sales – Build relationships with business owners through face-to-face outreach and tailored insurance solutions.

• Facilitate Growth – Train and mentor new agents with patience, structure, and encouragement in the field.
  Stay Focused & Accountable – Take ownership of your schedule, territory, and income.

• Build Trust – Foster long-term relationships with clients and colleagues through consistency and follow-through.

Why This Role Stands Out

• Reliable + Unlimited Pay – Weekly base draw plus uncapped commissions & bonuses

• Licensing Support – We cover state licensing fees after certain metrics are met

• Clear Leadership Pathway – Step confidently into mentorship and training roles

• Autonomy with Support – Manage your own success while backed by a collaborative team

• Meaningful Impact – Protect businesses and families while leaving a lasting mark

What We're Looking For

• Resilient & Focused – You adapt, persevere, and keep moving forward

• Facilitator at Heart – You enjoy coaching, guiding, and helping others grow

• Sales Experience – At least 1 year of B2B sales success

• Strong Communicator – Confident in presenting, coaching, and relationship building

• Organized & Motivated – Able to balance independence with team collaboration

Additional Requirements:

• Driver's license + reliable transportation

• Occasional overnight travel within territory

• Smartphone/iPad with data plan

• Willingness to obtain a state Health & Life license (Assistance with licensing and reimbursement)

Compensation & Benefits

• $80,000–$100,000+ annually, based on performance

• Weekly base draw + uncapped commissions + bonuses

• Quarterly & annual incentives: bonuses, trips, stock options

• Short sales cycle (average 3 days)

• CRM, mentorship, and structured training provided

Lead by Facilitating, Succeed by Growing

If you're focused, resilient, and passionate about helping others succeed, this role offers the platform to build your career while guiding others along the way.

www.canyoncreekfinancial.com