Inside Sales Representative

1 week ago

Markham, Ontario, Canada Pineapple Full time

Company Description

Pineapple Financial Inc. (NYSE: PAPL) is a Canadian mortgage technology and brokerage company revolutionizing the home financing experience for brokers, lenders, and clients. Through our platform, we deliver smarter, faster, and more transparent mortgage solutions by leveraging advanced analytics and marketing automation. In 2025, Pineapple became the first publicly traded company to hold INJ, the native token of Injective, highlighting our commitment to innovation at the crossroads of traditional finance and blockchain technology.

Role Description

This is a full-time on-site role located in North York, ON and we are looking for a high-energy, motivated
Inside Sales Representative
to support our mortgage agent recruitment efforts with a starting salary range of $40-45k.

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.

Duties and 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

Qualifications

  • 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

  • Inside Sales Representative

    1 week ago

    Markham, Ontario, Canada Apex Systems Full time

    Inside Sales RepresentativeApex Systems is a global IT services provider, and our staffing practice has an opening for anInside Sales Representativeto place at our client, within Enterprise Home Services.Location :North York, ONRate:$18.00/ hrHours:40 hoursApplication Process:Please submit your resume via the platform you are using. If you encounter any...

  • Inside Sales Representative

    4 days ago

    Markham, Ontario, Canada Toro Steel Buildings Full time

    Inside Sales Representative PositionAre You Ready to Build the Career and Life You Deserve?Inside Sales Representative – Unlimited Earning PotentialDo you want a role where your hard work is recognized, your growth is supported, and your success is in your hands? Are you motivated by results, driven by goals, and excited to make a real impact? If so, this...

  • Inside Sales Specialist

    3 days ago

    Markham, Ontario, Canada Kelly Services (Canada), Ltd. Full time

    Advisor, Accounts - Inside Sales | North York, ON (100% On-site)Pay Rate:$29.28/hr = 4% vacation payWork Schedule:Monday–Friday, 40 hours/week (Core hours 9am–4pm)Location:North YorkDuration:ASAP to Jan. 18, 2027This is for a current openingAI will not be used in the interview process.Are you ready to take the next step in your sales career?Seeking a...

  • Inside Sales Manager

    1 week ago

    Markham, Ontario, Canada 8Twelve Mortgage Full time

    Join the 8Twelve team and be part of revolutionizing the home financing experience in Canada Our proprietary end-to-end mortgage cloud platform INFIN8 provides brokers and borrowers with one-stop solution for all their mortgage needs. With real-time analytics and AI, we reduce approval times and identify the best financing solution available in Canada's...

  • Sales Representative

    4 days ago

    Markham, Ontario, Canada Stallion Express Full time

    Stallion Express is looking for a Sales Representative with turbo-charged skills and drive. You will be responsible for acquiring new clients through outbound methods (email, calls, face-to-face meetings) and creating content for inbound marketing (creating visual content for videos or facebook ads).Here are some requirements we are looking for:EXCELLENT...

  • Customer Sales Representative

    1 week ago

    Markham, Ontario, Canada c0-0269-40d9-a0a8-110d60489563 Full time

    Customer Sales Representative – NEW EXPANSIONMarkham, ON | Full-Time | In-PersonWestpoint AcquisitionsWe're Expanding to Toronto — and We're Hiring Customer Sales RepresentativesWestpoint Acquisitions is growing fast across Eastern Canada, and Markham is our next big move. We're building a team of Customer Sales Representatives to represent national...

  • Sales Representative

    1 week ago

    Markham, Ontario, Canada Neo Financial Full time

    Join us to build a more rewarding financial future for all CanadiansAt Neo, we're on a mission to build a more rewarding financial future for all Canadians. Life at a rapidly scaling tech startup isn't for everyone. It's complex, fast-paced, high-pressure, but also incredibly fulfilling. Since its founding in 2019, Neo has gained incredible traction and is...

  • Sales Representative

    1 week ago

    Markham, Ontario, Canada Neo Financial Full time

    Join us to build a more rewarding financial future for all CanadiansAt Neo, we're on a mission to build a more rewarding financial future for all Canadians. Life at a rapidly scaling tech startup isn't for everyone. It's complex, fast-paced, high-pressure, but also incredibly fulfilling. Since its founding in 2019, Neo has gained incredible traction and is...

  • Dental Sales Representative

    1 week ago

    Markham, Ontario, Canada Frontier Dental Supply Full time

    Come work with us to do what you love and stay for the Frontier TRACK …Team Centric: We each take responsibility for fostering an environment of personal and professional growth. We are eager to help, support and collaborate with one another recognizing that we are better when we work together.Respectful and Inclusive: We treat everyone the way we want to...

  • Technical Sales Representative

    2 days ago

    Markham, Ontario, Canada John Brooks Full time

    Department: PumpLocation/ Territory: North Eastern OntarioWHAT DO WE DO?We create solutions for the people who keep our world flowing.For over 80 years, John Brooks Company has been solving fluid handling challenges for customers in various industries/markets across Canada by providing a diverse selection of engineered products and innovative system designs,...