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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Why You’ll Love This Role

This is an entry-level outside sales opportunity focused on selling business-to-business supplemental insurance solutions. The role is commission-based with strong upside and is offered with flexible/remote work options. You will receive tools, training, and licensing support to ramp quickly and maximize earnings while working with a collaborative sales team.

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What You’ll Do

• Build relationships with business clients and sell supplemental insurance products tailored to employer and small-business needs
• Manage leads and follow-up using the company CRM to drive pipeline and close deals
• Own territory outreach, prospecting, and face-to-face or virtual sales meetings as needed
• Collaborate with peers and leadership to share best practices and refine sales strategies
• Maintain accurate records and meet or exceed monthly sales KPIs

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Who We’re Looking For

• Motivated self-starters with an entrepreneurial mindset and a drive to exceed goals
• Candidates with 4+ years of post-high-school experience; a bachelor’s degree is helpful but not required
• Strong communicators who enjoy helping clients and building long-term business relationships
• Comfortable working as an independent contractor/commission-based salesperson with CRM tools and a performance-driven culture

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Key Qualifications

• Sales aptitude or prior sales experience (entry-level candidates with demonstrable drive are encouraged)
• Comfortable with B2B selling and relationship-building
• Ability to learn product details and licensing requirements; company provides licensing assistance and reimbursement where applicable
• Reliable transportation for in-person client visits when required, and ability to work remotely as needed
• Authorization to work in the United States

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Compensation & Perks

• Commission-based compensation with uncapped earning potential (average reps earn approximately $65,000–$85,000/year)
• Starting base draw, licensing assistance, and reimbursements to support early ramp-up
• CRM, training, and a supportive sales team to help you grow quickly
• Independent-contractor flexibility with opportunities for high performers

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Location & Employment Type

• Location: Newberg, OR (Flexible / Remote options)
• Employment type: Commission-based / Contractor (telecommute-friendly)
• Note: Remote-capable role; applicants should be authorized to work in the U.S.

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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.