Job Overview

We're seeking a results-driven, highly persuasive Appointment Setter to drive outbound business development across local commercial accounts. Working directly with the Principal Agent, your primary goal is to conduct targeted cold calling to business owners, HR directors, and company executives to secure 2 to 5 qualified appointments per week. In this high-volume outreach role, you will deliver compelling value propositions, navigate gatekeepers, qualify employer needs, and schedule 15-to-30-minute discovery calls or on-site consultation meetings on the agent's calendar. Commissions will be provided if meeting sales targets.

Client Overview

Our client is an independent insurance agent affiliated with a leading supplemental benefits provider, servicing small-to-medium business owners across Appleton, Wisconsin, and the surrounding region. Specializing in voluntary employee benefit solutions, supplemental healthcare, and business coverage plans, the agency helps local employers attract and retain top talent at zero net cost to the business. To expand local market penetration and book qualified decision-maker meetings, they are onboarding a dedicated remote B2B Cold Caller & Appointment Setter.

Schedule: Monday - Thursday, 9:00 AM - 5:00 PM CT (20 work hours per week)

Responsibilities Outbound Cold Calling & Prospecting:

• Conduct targeted outbound cold calls to local small and mid-sized business owners, HR decision-makers, and key executives using provided prospect lists.
• Deliver clear, concise, and compelling phone scripts highlighting the value of voluntary supplemental benefit programs for business owners and employees.
• Overcome common objections, build immediate rapport, and navigate gatekeepers to reach primary decision-makers.

Appointment Scheduling & Pipeline Management:

• Secure and confirm 2 to 5 qualified 15-to-30-minute consultation appointments per week on the Principal Agent's Google/Outlook calendar.
• Send immediate calendar invites, confirmation emails, and pre-meeting reminder notes to prospective business owners.
• Accurately log call outcomes, disposition codes, business notes, and follow-up tasks in the CRM.
• Maintain a clean pipeline of warm leads for structured multi-touch follow-up cycles.

Requirements

• Cold Calling & Appointment Setting Track Record: 2+ years of outbound cold calling experience in B2B phone sales, appointment setting, or business development (prior experience in insurance, commercial sales, or merchant services is an advantage).
• Performance Consistency: Ability to achieve target appointment volumes (2–5 booked meetings per 20 call-hours) in competitive markets.
• Exceptional Verbal Communication: Fluent, professional spoken English with a clear, engaging tone and high confidence on the phone.
• Resilience & Objection Handling: Strong persistence, high call stamina, and the ability to turn initial resistance into scheduled discovery meetings.

Technical Stack & Tools

• Dialer & VoIP Systems: AirCall, RingCentral, JustCall, or Cloud PowerDialer
• CRM & Pipeline Tracking: HubSpot, Salesforce, or Google Sheets Lead Tracker
• Calendar & Communication: Google Workspace / Microsoft Outlook, Zoom

Independent Contractor Perks

• Permanent work from home

• Immediate hiring

Note

Please click the "Apply" button to complete your application, including the assessment questions, technical check, and voice recording. Your hourly pay rate will be established based on your performance in the application process; submissions with all requirements fulfilled will receive priority review.

One application, multiple possibilities: When you apply, our team reviews your background against all current openings, not just this one! If a different role fits your skills, we'll get in touch! We also encourage you to keep exploring our job board and apply directly to any position that excites you.