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Remote Leadership Jobs in Bend, OR (NOW HIRING)

HMG Careers

Sales Coordinator Remote

Sisters, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Consultant Remote

Sisters, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Remote Sales Representative

Sisters, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Consultant Remote

Bend, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Remote Benefits Advisor

Bend, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Remote Sales Manager

Bend, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Coordinator Remote

Bend, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Representative Remote

Bend, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Coordinator Remote

Bend, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Remote Sales Representative

Redmond, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Consultant Remote

Terrebonne, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Consultant Remote

La Pine, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Coordinator Remote

Culver, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Remote Sales Representative

Prineville, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Remote Sales Representative

Bend, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Sales Coordinator Remote

Terrebonne, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

HMG Careers

Remote Sales Manager

Bend, OR · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers ... High-quality leads provided with no cold calling friends or family * Flexible scheduling within a ...

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Showing results 1-20

All JobsLeadership JobsRemote Leadership JobsRemote Leadership Jobs in Bend, OR

Remote Leadership information

See Bend, OR salary details

$16

$29

$39

How much do remote leadership jobs pay per hour?

As of Aug 18, 2026, the average hourly pay for remote leadership in Bend, OR is $29.20, according to ZipRecruiter salary data. Most workers in this role earn between $22.84 and $35.00 per hour, depending on experience, location, and employer.

What is remote leadership?

A Remote Leadership job involves managing and guiding a team or organization from a distance, using digital tools for communication, collaboration, and performance management. Leaders in remote roles focus on maintaining productivity, fostering team engagement, and ensuring clear communication despite the lack of in-person interaction. Effective remote leadership requires strong skills in digital communication, adaptability, and trust-building.

What are the key skills and qualifications needed to thrive in remote leadership?

To thrive in a Remote Leadership role, you need proven experience in managing distributed teams, strategic planning, and excellent digital communication skills, often backed by formal leadership training or a relevant degree. Familiarity with collaboration platforms like Slack, Zoom, Asana, and remote project management tools is typically required. Emotional intelligence, adaptability, and proactive problem-solving distinguish great remote leaders. These skills are crucial for fostering engagement, driving productivity, and maintaining cohesion across geographically dispersed teams.

What are some common challenges remote leaders face, and how can they be effectively addressed?

Remote leaders often encounter challenges such as building strong team relationships, maintaining clear communication, and ensuring accountability without face-to-face interactions. To overcome these, successful remote leaders set clear expectations, use regular video check-ins, and leverage collaborative digital tools to keep everyone connected. Creating a culture of openness and trust is vital, as is recognizing achievements to keep team members motivated. Proactively addressing time zone differences and encouraging social interaction can also help foster a supportive remote work environment.

What are the most commonly searched types of Leadership jobs in Bend, OR?

The most popular types of Leadership jobs in Bend, OR are:

What are popular job titles related to Remote Leadership jobs in Bend, OR?

For Remote Leadership jobs in Bend, OR, the most frequently searched job titles are:

What job categories do people searching Remote Leadership jobs in Bend, OR look for?

The top searched job categories for Remote Leadership jobs in Bend, OR are:

What cities near Bend, OR are hiring for Remote Leadership jobs?

Cities near Bend, OR with the most Remote Leadership job openings:

Remote Leadership jobs near you
Infographic showing various Remote Leadership job openings in Bend, OR as of August 2026, with employment types broken down into 62% Full Time, 18% Part Time, and 20% Contract. Highlights an 100% Remote job distribution, with an average salary of $60,728 per year, or $29.2 per hour.

Remote Insurance Advisor(80k - 300k) - (No Cold Calling, Leadership Track)

SIL Advisor LLC

Bend, OR • Remote

$5.0K - $8.0K/wk

Full-time

Posted 8 days ago

Job description

Remote Insurance Advisor | Independent Contractor (1099)

Not Everyone Is Looking for a Job.

Some people are looking for a chance to build something bigger.

At SIL Advisor, we're partnering with motivated individuals who want flexibility, income potential, personal growth, and the ability to create a business of their own within the insurance industry.

Whether you're transitioning careers, seeking a better income opportunity, or simply tired of having your earnings capped, this opportunity offers a pathway to build a rewarding business from home.

No insurance experience is necessary. We provide the training, mentorship, systems, and support to help you get started.

What Makes This Different?

This is an entrepreneurial opportunity, not a traditional employee position.

As an independent contractor, you'll have the freedom to manage your schedule, develop your skills, and determine your income through your effort and performance.

The individuals who succeed here view themselves as business owners, not employees.

Your Day-to-Day

• Connect with clients virtually using phone and video appointments
• Guide individuals and families through life and health insurance options
• Follow up with prospects generated through company lead programs
• Build relationships and provide excellent client service
• Participate in coaching sessions and professional development
• Track activity and maintain consistent follow-up habits

What SIL Advisor Brings to the Table

• Company-generated lead opportunities
• Step-by-step onboarding and training
• Ongoing mentorship from experienced producers
• Access to a broad portfolio of insurance carriers
• Fully remote work environment
• Weekly commission payments
• Bonus opportunities based on production
• Leadership development programs
• Opportunity to build and scale your own agency

Compensation

This is a commission-only position with no cap on earnings.

Compensation is based on issued business and production results.

Many agents earn:

• $50,000+ annually on a part-time schedule
• $80,000–$300,000+ annually full-time
• Additional income through leadership and agency-building opportunities

Who Typically Excels

• Individuals with strong personal discipline
• Competitive and goal-focused personalities
• People willing to accept coaching and feedback
• Professionals seeking greater control over their income
• Those comfortable taking initiative and solving problems
• Individuals committed to long-term growth

Requirements

• Must live within the United States
• Must be legally authorized to work in the U.S.
• Ability to pass a background check
• Insurance license not required at application
• Willingness to obtain a Life & Health Insurance License
• Strong internet connection and professional communication skills

Before Applying

Please understand that this opportunity is best suited for individuals who are ready to take ownership of their results.

There is no hourly wage or guaranteed salary. Success is determined by consistency, effort, coachability, and execution.

If you're looking for a career path with mentorship, flexibility, uncapped income potential, and a chance to build something of your own, we'd like to connect with you.

Apply today to learn more about becoming part of the SIL Advisor team.