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 earning potential 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 (Supplemental B2B Insurance).
Applicants for this role may also receive access to additional matched opportunities through the Careertakes platform.
Role Overview
Confidential Client is seeking an Entry-Level Outside Sales Representative to sell business-to-business supplemental insurance solutions. This commission-based role offers independent-contractor autonomy, CRM tools, licensing support, and a high-earning upside for motivated, results-driven sellers. The role is flexible and can include remote work.
Estimated compensation: $92,654 per year (estimated). Typical/average reps historically earn $65,000–$85,000/year. This role is commission-based with uncapped bonuses and includes an initial base draw, licensing assistance, and reimbursement for certain startup costs.
Why You’ll Love Working Here
- Uncapped earnings potential — commission-based pay with performance bonuses.
- Support to succeed — starting base draw, licensing assistance, and reimbursements.
- Modern sales tools — CRM and lead-management resources provided.
- Flexibility & autonomy — independent-contractor style work and remote-friendly options.
Who We're Looking For
- Motivated self-starters and entrepreneurs comfortable with a commission-based compensation model.
- Candidates with 4+ years of post–high school experience; a bachelor’s degree is a plus but not required.
- People who enjoy helping businesses solve problems and can build trusted B2B relationships.
- Sellers who are coachable, resilient, and focused on measurable results.
What You’ll Do
- Prospect, build relationships, and sell supplemental insurance solutions to business clients (B2B).
- Manage pipelines and follow up on leads using the provided CRM.
- Close deals and track performance against targets.
- Collaborate with other sales team members to share strategies and scale success.
Qualifications
- 4+ years of post–high-school experience (work experience may substitute for degree).
- Proven self-starter mentality; comfortable in a target-driven, commission-first environment.
- Strong communication and relationship-building skills.
- Comfortable using CRM systems and basic sales technology.
- Licensing support is provided; active insurance license not required at application.
Compensation & Benefits
- Estimated compensation: $92,654/year (estimated); average reps historically earn $65K–$85K/year.
- Commission-based pay with uncapped upside and bonus opportunities.
- Initial base draw and licensing assistance to help you get started.
- Reimbursement for approved startup costs and access to CRM tools.
- Independent-contractor autonomy with structured team support.
Notes & Legal
- This listing is posted by Careertakes on behalf of a Confidential Client in the Insurance (Supplemental B2B Insurance) industry.
- Position is commission-based and may be structured as contractor engagement; state-specific employment classifications and benefits will be determined by the hiring organization and in compliance with applicable laws (including California pay-transparency rules).
- Salary information shown above reflects figures provided in the source posting (estimated annual figure and historical averages) and is included for transparency.
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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