About Careertakes

👉 Important disclosure: Careertakes is a third-party recruiting platform supporting this hiring process. If selected, you will be employed directly by our client, Insurance.

Applicants for this role may also receive access to additional matched opportunities through the Careertakes platform.

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Overview

Confidential Client is hiring an Entry-Level Outside Sales Representative to sell business-to-business supplemental insurance solutions. This is a commission-based, flexible/remote opportunity based in Sandy, OR (local candidates preferred). The role is ideal for motivated, entrepreneurial self-starters who want uncapped earnings, licensing support, and the tools to build a high-impact sales career.

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What You’ll Do

• Build relationships with business clients and present supplemental insurance solutions
• Qualify leads, manage pipeline, and close deals using the company CRM
• Maintain accurate records of prospect and client interactions in the CRM
• Collaborate with team members to refine sales approaches and share best practices
• Manage your schedule as an independent contractor while meeting performance targets

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Who We’re Looking For

• Motivated self-starters with at least 4+ years of post–high-school experience (degree is a plus but not required)
• Entrepreneurial mindset and a proven ability to set and exceed goals
• Strong communication and relationship-building skills
• Comfortable using a CRM and learning sales tools quickly
• Passionate about helping clients and delivering measurable results

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Compensation & Benefits

• Commission-based pay with uncapped earning potential
• Typical earnings range for successful reps: $65,000–$85,000 per year (varies by performance)
• Estimated market salary shown: $84,400/year (for reference)
• Starting base draw, licensing assistance, and reimbursement to get licensed
• Access to CRM and sales tools; autonomy as an independent contractor
• Remote/flexible work with opportunities to collaborate with a high-performing team

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Employment Type & Location

• Employment type: Contractor / Commission-based
• Location: Sandy, OR (Flexible / Remote options available)
• Job requires eligibility to work in the U.S.; local or remote applicants in the U.S. are welcome

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Equal Opportunity & Hiring Transparency

Careertakes and our client are Equal Opportunity Employers committed to building a diverse and inclusive workforce. We prohibit discrimination or harassment of any kind. To support a fair and efficient hiring process, AI tools may be used to assist with application review or resume screening. These tools do not replace human decision-making. Final hiring decisions are made by people.

If you have questions about how your data is used, please contact us directly.