Outside Sales Representative Entry-Level
The Entry-Level Outside Insurance Representative at Confidential Client is a commission-based sales role focused on selling supplemental insurance solutions to businesses. This fully remote position requires motivated self-starters with entrepreneurial drive to build client relationships, manage leads using CRM tools, and collaborate with a high-performing team to achieve uncapped earnings and professional growth.
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.
Why You'll Love Working Here
- Commission-based role with uncapped bonuses and strong upside potential
- Estimated compensation: commission-focused with typical earnings between $65,000–$91,363 per year (average reps earn $65K–$85K/year)
- Support to succeed: starting base draw, licensing assistance, and reimbursement for required onboarding
- Flexible / remote work options and access to a CRM and other sales tools
- Independent-contractor-style autonomy while collaborating with a high-performing sales team
Key Responsibilities
- Build relationships and sell business-to-business supplemental insurance solutions to employers and decision-makers
- Manage leads and pipeline using the provided CRM to progress opportunities to close
- Develop territory strategies, identify prospects, and execute outreach to meet sales targets
- Collaborate with team members to share best practices and improve conversion rates
- Maintain compliance with licensing and company policies while documenting activity and results
Who We're Looking For
- Motivated self-starters with 4+ years of post–high-school experience; a bachelor’s degree is a plus but not required
- Entrepreneurial sellers who thrive on measurable goals, persistence, and high activity levels
- Strong communicators who enjoy helping clients and explaining benefits clearly
- Comfortable working in a commission-driven environment and using a CRM to drive outcomes
What You’ll Get
- Commission-based pay with uncapped earning potential and performance bonuses
- Licensing assistance, initial base draw, and reimbursement to help you ramp quickly
- CRM, sales resources, and ongoing coaching from experienced peers
- Remote / flexible work arrangement with opportunities for in-person collaboration as needed
Qualifications (Preferred)
- 4+ years of work experience after high school
- Sales orientation and proven ability to meet or exceed targets (any industry)
- Comfortable presenting to business decision-makers and managing a sales pipeline
- Self-motivated, organized, and able to work independently with accountability
Other Details
- Employment type: Commission-based, independent-contractor style (role may be structured as contract compensation)
- Location: Corvallis, OR (flexible / remote work options available)
- Industry: Insurance
- Note: Confidential Client is the hiring organization for this role.
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.
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