Opportunity at
WorkleapSales Development Representative — ShareGate
Workleap is seeking a Sales Development Representative to focus on ShareGate and serve as the initial point of contact for potential customers. Founded in 2006, the…
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About This Role
Workleap is seeking a Sales Development Representative to focus on ShareGate and serve as the initial point of contact for potential customers. Founded in 2006, the Montreal-based technology company builds software utilized by over 15,000 organizations worldwide, including products designed for Microsoft 365 migration and governance alongside tools for managerial effectiveness. In this role, you will initiate conversations with IT buyers through inbound follow-ups and outbound prospecting to build a…
Job Description
Workleap is seeking a Sales Development Representative to focus on ShareGate and serve as the initial point of contact for potential customers. Founded in 2006, the Montreal-based technology company builds software utilized by over 15,000 organizations worldwide, including products designed for Microsoft 365 migration and governance alongside tools for managerial effectiveness. In this role, you will initiate conversations with IT buyers through inbound follow-ups and outbound prospecting to build a consistent, qualified pipeline for the account executive team. You will operate alongside an AI agent to handle routine outreach while concentrating on high-value accounts, phone calls, and complex manual tasks. The position sits within a four-person team focused on ShareGate and emphasizes internal promotion and career advancement in B2B sales.
Responsibilities
- Initiate outbound prospecting and inbound follow-up to generate qualified pipeline for account executives
- Evaluate prospects consultatively to understand their challenges and readiness prior to handoff
- Research target accounts and multi-thread into IT organizations using calls and sequences
- Manage and improve an AI agent designed to handle routine outbound batches and simple leads
- Maintain deep product knowledge across ShareGate Protect and Migrate offerings and target IT personas
- Develop and refine AI workflows and automations for call preparation, account research, and follow-ups
- Contribute fresh ideas to the team process regarding AI utilization and sales approaches
Requirements
- Active daily utilization of AI tools such as Claude or ChatGPT
- Strong English verbal communication skills with phone and video presence
- Previous experience in a sales or performance-driven position such as SDR, BDR, or inside sales
- Background in outbound prospecting including cold calling and multi-touch sequences
- Ability to learn complex B2B products and buyer profiles quickly
- Pipeline discipline to prioritize, track, and advance multiple parallel conversations
Qualifications
- Prior background in SaaS or the technology sector
- Familiarity with HubSpot, Gong, or LinkedIn Sales Navigator
- Proficiency in communicating in French
- Demonstrated examples of personally built AI tools or workflows
Core Skills
Benefits
- Base salary ranging from $55,000 to $60,000 per year with an OTE of $85,000 to $90,000
- Long-Term Incentive Plan program participation
- RRSP contributions
- Family health insurance and telemedicine coverage
- Annual wellness budget
- Flexible vacation policy
- Access to the Montreal office and remote work flexibility with twice-yearly in-person gatherings
- Access to Claude for all employees
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the salary and OTE for the Sales Development Representative role?
The base salary ranges from $55,000 to $60,000 per year, with an OTE of $85,000 to $90,000 based on a Canada-wide compensation scale.
What is the remote work policy for this position?
The role offers remote work flexibility with access to the Montreal office and requires attending in-person gatherings twice a year.
What experience is required for this job?
Candidates must have prior experience in a sales or performance-driven role like an SDR, BDR, or inside sales, along with outbound prospecting experience and active daily use of AI tools.
How can I apply for this position?
The job posting does not specify a direct application link beyond confirming the review of the company privacy policy.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.
