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Sales Development Representative — ShareGate

WorkleapCanada - RemoteSales
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Salary
$55K - $60K USD
Job type
Full-time
Work mode
Remote
Posted
7 Aug 2026
Status
Open · checked 7d ago

About this role

Role Overview

The Sales Development Representative role at Workleap is a remote position based in Canada that focuses on initiating conversations with IT buyers to build a strong pipeline for the account executive team. This opportunity suits an ambitious sales professional who is eager to launch a B2B sales career and utilize AI tools to enhance daily workflows.

Key Responsibilities

Drive a consistent and qualified pipeline for the account executive team by reaching out to IT buyers through inbound follow-ups and outbound prospecting.
Qualify prospects thoroughly by understanding their specific challenges and readiness before handing them over with full context.
Conduct outbound prospecting by researching target accounts, executing sequences, calling IT teams, and multi-threading.
Operate and improve an assigned AI agent that manages outbound batches and simple leads, allowing focus on high-value accounts and manual tasks.
Maintain deep product knowledge across ShareGate offerings and IT buyer personas to deliver expert-level conversations.
Build and refine AI systems and prompts for call preparation, account research, and follow-up communications.

Requirements

Active daily use of AI tools like Claude or ChatGPT to improve work efficiency and readiness to learn new tools.
Strong verbal communication skills in English with a confident presence on phone and video calls.
Prior experience in a sales or performance-driven position such as an SDR, BDR, or inside sales role with a history of meeting targets.
Demonstrated outbound prospecting experience, including cold calling and multi-touch sequences.
Capacity to quickly learn complex B2B products and understand the buyers who use them.
Strong pipeline discipline to prioritize, track, and advance multiple concurrent conversations.

Nice to Have

Background in SaaS or the tech industry.
Familiarity with tools such as Gong, LinkedIn Sales Navigator, or HubSpot.
Ability to communicate in French.
Personal examples of built AI workflows or tools.

Skills and Tools

Outbound prospecting and cold calling
Pipeline management and discipline
B2B consultative qualification
AI tool utilization including Claude and ChatGPT
Communication skills in English

Salary and Benefits

Base salary ranging from $55,000 to $60,000 USD per year, with an OTE of $85,000 to $60,000 USD.
Long-term incentive plan (LTIP) to share in company growth.
RRSP contribution matching.
Family health insurance and telemedicine coverage.
Annual wellness budget.
Flexible vacation policy.
Remote work flexibility with access to the Montreal office and biannual in-person gatherings.
Claude access provided for all employees.

About the Company

Workleap is a Montreal-headquartered tech company founded in 2006 that builds practical software products, including Workleap Agent and the ShareGate Microsoft 365 migration and governance solution. Over 15,000 companies globally rely on its products to improve the work experience. The organization values speed, internal promotion, and the integration of AI to accelerate work without replacing human judgment.

How to Apply

To apply for this remote position, visit the official company careers page and submit your application.

Questions candidates ask

What is the location of the Sales Development Representative position?

The position is remote based in Canada, with optional access to the Montreal office and biannual in-person team gatherings.

What is the salary and OTE for this role?

The base salary ranges from $55,000 to $60,000 USD per year, with an On-Target Earnings (OTE) range of $85,000 to $90,000 USD, adjusted based on the candidate's region.

What experience is required for this job?

Candidates need experience in a sales or performance-driven role like an SDR, BDR, or inside sales position, alongside outbound prospecting experience and daily usage of AI tools.

What benefits are included with employment?

Benefits include an LTIP program, RRSP, family health insurance, telemedicine, an annual wellness budget, flexible vacation, and access to Claude.

How does the hiring process work?

The process includes an initial call with a recruiter, a virtual interview with the hiring manager, a take-home case study, and a follow-up meeting with future colleagues.

Ready to apply?

The application is on the official Workleap careers page.

Apply on company site