Job Title: Inside Sales Representative

Focus: Mortgage Agent Recruitment (Phone-Based)
Company: Pineapple Financial
Location: In Office / Onsite – 111 Gordon Baker Rd, North York, ON M2H 3R1
Employment Type: Full-Time

About Pineapple Financial

Pineapple Financial is a fast-growing, technology-driven mortgage brokerage redefining how Canadians access home financing. We combine innovative digital tools with expert advice to empower our agents and deliver an exceptional client experience nationwide.

As we continue to scale, we’re looking for a high-energy, motivated Inside Sales Representative to support our mortgage agent recruitment efforts. This role is ideal for someone who enjoys meaningful conversations, thrives on outbound outreach, and gets energized by identifying the right people—not just more people.

The Role

In this role, you will be the first point of contact for licensed mortgage agents who may be open to new opportunities. Your primary responsibility is to engage agents by phone, qualify their interest and fit, and book high-quality meetings with Pineapple’s Director of Sales and leadership team.

This is not a transactional sales role. It’s a relationship-driven, consultative outreach position focused on identifying strong agents who align with Pineapple’s values, culture, and growth vision.

You will play a critical role at the top of the recruitment funnel and have a direct impact on the company’s expansion across Canada.

Key Responsibilities

• Conduct high-volume outbound calls to licensed mortgage agents across Canada
• Clearly and professionally communicate Pineapple’s value proposition
• Engage agents in meaningful conversations to assess interest, experience, and readiness
• Qualify prospects based on production, background, and cultural alignment
• Schedule and confirm meetings between qualified agents and the Director of Sales
• Maintain accurate and detailed call notes, updates, and follow-ups in the CRM
• Follow up with prospects via phone, email, and text to nurture interest
• Consistently meet or exceed daily activity targets and monthly meeting goals (KPI’s)
• Collaborate closely with sales leadership to refine messaging and outreach strategy
• Support additional sales and recruitment initiatives as needed
  

What You Bring

• Proven experience in phone-based sales, inside sales, appointment setting, or recruitment outreach
• Confident, professional phone presence with strong rapport-building skills
• Excellent communication and active listening abilities
• Comfortable handling objections and navigating professional conversations
• Highly organized with strong follow-up discipline and attention to detail
• Tech-savvy and comfortable working with CRM systems
• Experience in mortgages, financial services, insurance, or real estate is a strong asset
• Self-motivated, resilient, and goal-oriented mindset
  

Why Join Pineapple

• Be part of a fast-growing, award-winning fintech mortgage brokerage
• Work directly with senior leadership and decision-makers
• Have a clear, measurable impact on company growth
• Supportive, collaborative, and performance-driven team culture
• Competitive base compensation with performance-based incentives
  Clear growth opportunities within a scaling organization
  

How to Apply

Please submit your resume and a brief cover letter explaining why you’d be a great fit for the Pineapple team to allan@gopineapple.com.