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Outside Sales Representative Trainer Jobs in Springfield, OR

Diamond Financial

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Outside Sales Representative

Eugene, OR · Remote

$75K - $125K/yr

You'll receive comprehensive training, ongoing sales and leadership development, and a proven ... What You'll Do As an Outside Sales Representative, you will work directly with local businesses to ...

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All JobsOutside Sales Representative Trainer JobsOutside Sales Representative Trainer Jobs in Springfield, OR

Outside Sales Representative Trainer information

See Springfield, OR salary details

$31.1K

$80.8K

$171.3K

How much do outside sales representative trainer jobs pay per year?

As of Sep 5, 2026, the average yearly pay for outside sales representative trainer in Springfield, OR is $80,776.00, according to ZipRecruiter salary data. Most workers in this role earn between $54,300.00 and $93,200.00 per year, depending on experience, location, and employer.

What is an outside sales representative trainer?

An Outside Sales Representative Trainer is a professional responsible for training and developing outside sales representatives, who typically work in the field meeting clients and generating sales. The trainer designs and delivers instructional programs, mentors new hires, and ensures sales teams have the skills and knowledge needed to achieve their targets. They may also observe sales interactions, provide feedback, and stay updated on best practices and market trends. This role is essential for organizations seeking to boost sales performance and maintain a competitive edge.

How does an outside sales representative trainer balance training responsibilities with field sales activities?

As an Outside Sales Representative Trainer, you will often split your time between conducting training sessions for new and existing sales team members and joining them in the field to demonstrate effective sales techniques. This dual responsibility requires strong time management and organizational skills, as you'll need to customize training approaches, review performance, and provide hands-on coaching during real client interactions. Collaboration with sales managers is common to ensure training aligns with team goals, and feedback from fieldwork often informs updates to training materials. This balance allows you to stay current with industry trends while supporting team development.

What are the key skills and qualifications needed to thrive as an outside sales representative trainer?

To thrive as an Outside Sales Representative Trainer, you need a strong background in sales techniques, training program development, and a proven track record in outside sales, often supported by a bachelor’s degree in business or a related field. Familiarity with CRM software, sales enablement tools, and learning management systems (LMS) is typically required, along with certifications like Certified Professional in Training Management (CPTM) being advantageous. Exceptional communication, coaching, and motivational skills help trainers engage sales teams and foster continuous improvement. These skills are vital for effectively transferring sales knowledge, driving team performance, and achieving organizational sales goals.

What is the difference between Outside Sales Representative Trainer vs Inside Sales Trainer?

AspectOutside Sales Representative TrainerInside Sales Trainer
CredentialsSales experience, training certificationsSales experience, training certifications
Work EnvironmentField, client sites, in-personOffice, call centers, virtual
Industry UsageCommon in B2B, manufacturing, wholesaleCommon in tech, retail, B2B
Primary FocusField sales skills, client engagementCall techniques, product knowledge

The main difference between an Outside Sales Representative Trainer and an Inside Sales Trainer lies in their work environment and focus. Outside Sales Trainers primarily prepare field sales reps for client-facing activities, while Inside Sales Trainers focus on call-based sales techniques. Both roles require sales experience and training certifications, but their daily tasks and settings differ significantly.

What are popular job titles related to Outside Sales Representative Trainer jobs in Springfield, OR?

For Outside Sales Representative Trainer jobs in Springfield, OR, the most frequently searched job titles are:

What cities near Springfield, OR are hiring for Outside Sales Representative Trainer jobs?

Cities near Springfield, OR with the most Outside Sales Representative Trainer job openings:

Outside Sales Representative Trainer jobs near you
Infographic showing various Outside Sales Representative Trainer job openings in Springfield, OR as of August 2026, with employment types broken down into 91% Full Time, and 9% Contract. Highlights an 100% In-person job distribution, with an average salary of $80,776 per year, or $38.8 per hour.

Outside Sales Representative & Trainer

Canyon Creek Financial LLC.

Springfield, OR • On-site

$80K - $100K/yr

Full-time, Contractor

Medical, Life

Re-posted 21 days ago

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: MondayFriday (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 numbersit'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 agentshelping 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.

Apply today and step into leadership with Canyon Creek Financial.

www.canyoncreekfinancial.com