Outside Sales Representative Entry-Level
The Entry-Level Outside Insurance Representative role at Confidential Client involves selling supplemental insurance solutions to businesses, leveraging CRM tools to manage leads and close deals. This commission-based, fully remote position rewards motivated self-starters with entrepreneurial drive, offering uncapped earning potential and support such as licensing assistance and a starting base draw.
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 / Financial Services.
Applicants for this role may also receive access to additional matched opportunities through the Careertakes platform.
Role Overview
Confidential Client is hiring an entry-level Outside Sales Representative to sell business-to-business supplemental insurance. This commission-first role is ideal for ambitious, self-motivated sellers who want uncapped earnings, licensing support, and autonomy while working with a high-performing sales team.
What You’ll Do
- Build relationships with business clients and present supplemental insurance solutions
- Manage leads and opportunities using the company CRM to move prospects through the sales cycle
- Close new business and meet or exceed monthly and quarterly sales targets
- Coordinate with team members to share best practices and improve conversion rates
- Maintain accurate records of activity and client interactions in CRM
Who We’re Looking For
- Motivated self-starters with 4+ years of post–high-school experience (BA preferred but not required)
- Entrepreneurial sellers who thrive on measurable results and continuous improvement
- Strong communicators who enjoy helping clients and building trust
- Comfortable working with a commission-based compensation plan and using sales technology (CRM)
Compensation & Benefits
- Commission-based with uncapped earning potential; average representatives earn roughly $65,000–$85,000/year (site estimate shown: $85,907/year)
- Starting base draw, licensing assistance, and reimbursements to support onboarding
- Access to CRM and sales tools, plus collaboration with an experienced sales team
- Independent-contractor autonomy with training and ongoing support
Location & Employment Type
- Primary market: Redmond, OR (Flexible / Remote work model available)
- Employment type: Commission-based, independent contractor (CONFIDENTIAL CLIENT will specify classification)
- Candidates must be authorized to work in the United States
Keywords & Core Skills
- Outside Sales Representative — Redmond, OR
- B2B supplemental insurance sales
- Entry-level sales (commission-based)
- CRM lead management
- Remote / flexible field sales
What to Expect
Careertakes will coordinate the initial candidate screening. If you move forward, Confidential Client will conduct interviews and make the final hiring decision. Licensing support and onboarding details will be provided to selected candidates.
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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