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, Supplemental Insurance / Financial Services.

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

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Outside Sales Rep North Fort Myers FL — Quick overview

Outside Sales Rep North Fort Myers FL — Join a confidential client in the supplemental insurance / financial services industry. This entry-level, territory-based field sales role includes classroom + field training, draw options plus uncapped commission, and benefits after introductory period.

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What You’ll Do

• Use a customized Salesforce CRM to identify leads, track activity, and manage your pipeline
• Conduct in-person visits to small and medium-sized businesses across an assigned territory
• Present supplemental insurance solutions to business owners, HR contacts, and groups (one-on-one and presentations to audiences of 50–100+)
• Schedule and follow up on meetings and referrals via phone, email, and text
• Maintain daily activity logs and record sales metrics in CRM
• Collaborate with your sales manager to set monthly and quarterly targets and plan territory activity
• Build and manage a client portfolio with an emphasis on renewals and long-term relationships
• Attend regular team meetings and coaching sessions; participate in field ride-alongs as requested

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Qualifications

• Reliable transportation and a valid Driver’s License
• Willingness to complete an active Health & Life Insurance Producer license in your resident state (study course provided at no cost; licensing fees reimbursement available)
• Pass a pre-employment background check
• Bachelor’s degree OR a minimum of 4 years post–high-school work experience (candidates within 6 months of degree completion or with relevant sales/athletic backgrounds are encouraged to apply)
• Strong communication and presentation skills; comfortable speaking to groups as well as individuals
• Self-motivated, organized, and able to manage a flexible schedule based on results
• Comfortable using CRM systems (Salesforce experience is a plus)

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Compensation & Benefits

• Weekly draw option plus commissions — uncapped; short sales cycle (typical payment in ~3 business days)
• Monthly cash sales bonuses, quarterly stock-share bonuses, incentive trips, and vested renewal commissions
• Health, dental, and vision benefits available after 60 days of employment
• Continuing professional development, advanced sales training, and leadership development classes
• Performance-based promotions and career growth opportunities
• Control of your schedule based on results rather than hours worked
• Supportive team culture with peer camaraderie and healthy competition

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What to Expect / Candidate Experience

• Comprehensive classroom training followed by mentored field training
• Territory-based schedule with regular travel within assigned area (local/regional)
• Reimbursement for state licensing fees and provided study materials for licensing
• Regular coaching, performance reviews, and measurable monthly goals
• Reasonable accommodations available during the hiring process upon request

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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.