Sales Development Representative - ShareGate

Company Description

Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, we make simple products that actually matter to the people who use them. We have two product lines: Workleap Agent, our newest solution built to make every manager more effective, and ShareGate, the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here.

Your role

You're the first voice prospects hear — and the first impression that sets the tone for every deal. As an SDR at ShareGate, your job is to start conversations with the right IT buyers, whether they raised their hand or not, and hand them to the AE team with everything they need to win. You'll work alongside your own AI agent that handles outbound batches and the easy-to-convert leads, while you focus on calls, high-value accounts, and the manual work that needs a human. This role exists because we're growing, because we promote from within, and because we're looking for someone who wants to build a real B2B sales career with a team that actually invests in making them better.

Your impact:

• Drive consistent, qualified pipeline for the AE team by starting conversations with IT buyers, through outbound prospecting and inbound follow-up, at a volume and quality that moves the needle on ARR;

• Qualify every prospect with a consultative lens: understand their reality, challenge, and readiness before pushing forward, so every handoff lands with context, not just contact info;

• Build outbound pipeline by researching target accounts, multi-threading into IT teams and running sequences and calls that start real conversations;

• Run and improve your own AI agent that handles outbound batches and easy-to-convert leads, so you can focus on calls, high-value accounts, and the manual work that needs a human;

• Own your product knowledge across both ShareGate products (Protect and Migrate) and the IT personas we serve, so every conversation is grounded in real expertise rather than a generic pitch;

• Build and refine AI systems for your workflow (prompts, custom assistants, automations for call prep, account research and follow-ups) and share what works so the whole team levels up;

• Bring fresh ideas and new approaches to the team's process, especially around AI, contributing to a culture where everyone makes the whole team better.

Your team

You're joining a four-person SDR team, all focused on ShareGate, feeding the AE org. That means the quality of what you pass downstream matters as much as the volume. The team is coached closely — Gong call reviews, roleplay sessions, custom AI tools, and a manager whose job is to help you grow. We move fast, share what's working, and hold each other to a high standard.

What you'll bring

• An active daily user of AI tools (Claude, ChatGPT, or equivalent) — not experimenting, actually using them to do better work, and ready to pick up new tools quickly;

• Strong verbal communication in English — confident on the phone and on video, with a presence that creates a memorable first impression for the right reasons;

• Experience in a sales or performance-driven role (SDR, BDR, inside sales) with a track record of hitting targets;

• Outbound prospecting experience (cold calling, multi-touch sequences) and the resilience that comes with it;

• The ability to quickly learn complex products and understand the buyers who use them in a B2B context;

• Pipeline discipline: you can prioritize, track, and advance multiple conversations in parallel without things slipping through;

• Bonus: SaaS or tech background; familiarity with Gong, LinkedIn Sales Navigator, or HubSpot; ability to communicate in French; examples of AI workflows or tools you've built yourself.

Most of this sounds like you? Apply.

What the job comes with

• Base salary: $55k - $60k/ OTE: $85k - $90k. This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate's region to align with local market conditions.

• LTIP program, share in Workleap's long-term growth.

• RRSP + Family health insurance + telemedicine + annual wellness budget.

• Flexible vacation policy.

• Remote work, with access to our Montreal office.

• In-person gathering twice a year.

• Claude access, for everyone.

What drives us

At Workleap, we build software that sits at the center of how people experience work, every day, at every level.

We move fast. Priorities shift, decisions get made with the information we have, and we iterate. If you thrive on intensity and ambiguity doesn't slow you down, you'll feel right at home.
We're builders. We do what it takes to move forward. AI is part of our toolkit. We use it to go faster and decide smarter, not to replace judgment.

If you want real impact and a place where your decisions matter, this is it.

How we hire

Transparency is how we hire — for you as much as for us.

Here's how it works: a first call with a recruiter, then a virtual interview with the hiring manager. You'll then complete a take-home case study, followed by a meet with future colleagues to discuss it together. Depending on the role, the process may vary slightly — your recruiter will walk you through it on your first call.

We use AI to support certain steps of the process, but every hiring decision remains human.

We can't wait to meet you.

By applying, you confirm that you have read and agree to our privacy policy.

#LI-Remote