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Outbound Sales Representative

Overview

Join a growing Ontario-based financial services agency and become the crucial first point of contact helping businesses access major cost-saving insurance and strategic tax planning solutions. In this high-impact role, you will leverage clear scripts and structured support to engage business owners, book high-value consultations, and earn lucrative commissions. This is a prime opportunity to drive real business growth while fast-tracking your career from the comfort of your home.

Schedule:

Part-time (20 hours per week); 4 hours daily, 1:00 PM to 5:00 PM EST Client Timezone: Eastern Time (Toronto, Ontario)

Responsibilities

  • Make outbound calls to businesses across Ontario to schedule valuable consultations
  • Present preferred insurance pricing opportunities using provided scripts
  • Book appointments for agents to deliver free general liability insurance quotes
  • Schedule consultations for tax strategy and financial planning services
  • Target niche market businesses where the agency offers competitive advantages
  • Maintain professional communication representing the insurance agency and The Cooperators
  • Follow up with prospects to confirm and optimize scheduled appointments
  • Adapt conversations to offer alternative services when initial offerings don’t resonate
  • Potentially assist with lead generation and list building using available tools

Requirements

  • Proven experience with cold calling and appointment setting, preferably in US or Canadian markets
  • Clear, professional English communication
  • Ability to work Eastern Time zone hours (Toronto, Ontario schedule)
  • Professional phone presence and demonstrated sales experience
  • Comfort with B2B outreach and business owner communication
  • Resilience with rejection and persistence in follow-up efforts
  • Bonus if you have basic understanding of insurance or financial services concepts
  • It helps if you have experience with lead generation tools and list building

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.

Outbound Sales Representative

Job Category

Administration

Job Type

Part Time (20 - 34 Hours per week)

Work Schedule and Timezone

Monday to Friday 1:00 PM to 5:00 PM Kingston, ON, Time.

Published on

May 26 2026