Sales Development Representative – B2B Software

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: TYPE OF WORK

Any

: SALARY

10CAD

: HOURS PER WEEK

TBD

: DATE UPDATED

Sep 17, 2026

JOB OVERVIEW

Sales Development Representative – B2B Software
Remote | 20 Hours/Week | 10am-2pm EST

About the Role
We are looking for an experienced SDR to help our Canadian technology company who provides 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 qualified demonstrations 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 solution
-Strong 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 activity
-Ability 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

How to Apply
Please submit your resume along with:
1. A 60–90 second video recording explaining why you’re the best fit for this role.

Please include the word POS – Your name in your application subject line.

SKILL REQUIREMENT

Outbound Sales Lead Generation Appointment Setting

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Sales Development Representative – B2B Software

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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