Remote | 20 Hours/Week | 10am-2pm EST

About The Role

We are an established Canadian technology company providing specialized point-of-sale and operational software to senior living and healthcare organizations across North America.

Our platform helps organizations manage dining operations, resident billing, payments, ordering, reservations, reporting, and other important workflows. We are hiring an experienced Sales Development Representative to identify prospective customers, conduct outbound outreach, qualify opportunities, and book product demonstrations for our sales team.

This is not a basic scripted call centre role. You must be confident speaking with business decision-makers, asking strong discovery questions, handling objections, and clearly communicating the value of a B2B software solution. Your success will be measured primarily by the number and quality of qualifieddemonstrations you book.

Key Responsibilities

Research senior living, healthcare, and related organizations in Canada and the United States
Identify relevant decision-makers and accurate contact information
Conduct outbound cold calls and personalized email outreach
Introduce the company and explain the value of its software solutions
Ask discovery questions to understand the prospect's current systems, challenges, and needs
Qualify prospects based on fit, interest, authority, and potential opportunity
Book qualified product demonstrations for the sales team
Follow up consistently with prospects and confirm scheduled meetings
Maintain accurate notes, activities, and next steps in the CRM
Meet weekly outreach, conversation, and qualified-meeting targets
Share feedback on objections, customer needs, and outreach messaging

Required Qualifications

At least 3 years of experience in B2B cold calling, sales development, appointment setting, lead generation, or inside sales
Proven success booking meetings with business decision-makers
Excellent spoken and written English
Clear, confident, and professional phone communication
Experience selling or promoting software, SaaS, technology, POS systems, or another B2B solutionStrong prospect research, lead
qualification, objection-handling, and follow-up skills
Ability to communicate naturally without sounding overly scripted or aggressive
Experience using a CRM to manage prospects and sales activityAbility to work during North American Eastern Time business hours
Reliable high-speed internet, a professional headset, and a quiet home workspace

Preferred Qualifications

Experience selling to senior living, healthcare, hospitality, dining, or multi-location organizations
Familiarity with POS systems, resident billing, payment technology, or operational software
Experience prospecting into the Canadian or US market
Experience speaking with executives, operators, administrators, finance leaders, or technology decision-makers
Long-term opportunity for a consistent, high-performing team member

Sales Development Representative B2B Software