Role overview

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: The Workleap Agent, our agentic HR platform that helps managers become better leaders, 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

We're looking for a Renewal Specialist who brings process discipline, commercial instinct, and a genuine drive to protect and grow customer relationships at scale. You'll own the renewal motion for our Flash segment — a high-volume SMB book where consistency, speed, and smart prioritization make the difference. You'll be the person customers hear from when it matters most: before their renewal, during their pricing migration, and when they need a clear reason to stay.

Your impact:

Own the end-to-end renewal motion for the Flash segment — running proactive 90/60/30-day cycles that keep GRR on target and surface expansion potential early;
Accelerate pricing migration conversations across your book — moving legacy per-seat customers to the new platform pricing model and closing them;
Maintain a clean, accurate HubSpot pipeline across a high-volume book so forecasting reflects reality, not optimism;
Identify expansion signals and collaborate with Account Managers on accounts that have outgrown the Flash motion;
Use AI tools (e.g. Claude) to personalize outreach at scale, prep for calls, and build account briefs fast — so your time goes toward conversations, not admin;
Catch early churn signals, escalate with a plan, and follow the playbook while knowing when to adapt.

Your team

As an Associate Account Manager at Workleap, you'll sit within a high-trust Account Management team that takes real pride in winning together. This isn't a siloed role — you'll work closely with Account Managers, Onboarding Specialists, and your manager to make sure customers in the Flash segment get real attention even at scale. The Renewal Desk is a proven motion here: we've built the playbook, we've seen the results, and now we're looking for the right person to own it.

The pricing migration is one of the most strategic plays of the year — moving customers from legacy per-seat pricing to our new platform model takes real commercial judgment, even at SMB scale. On top of that, we're pushing Workleap Agent adoption across the book, which means the renewal conversation isn't just about keeping a customer — it's about helping them see what's possible next. And as a recently expanded team, there's a real opportunity to help shape how this motion evolves.

What you'll bring

Bilingual French-English is a must;
1+ years in a renewal, inside sales, or customer success role where you owned a number — not just contributed to one;
Comfortable managing a high-volume account book; experience at SMB scale is a real advantage;
Strong pipeline discipline: CRM hygiene is a professional standard for you, not an admin tax;
Comfortable using AI tools (e.g. Claude, Copilot, ChatGPT) daily as a work accelerator — not an experiment, a habit;
Process-oriented with good instincts for when to stick to the playbook and when to adapt (Bonus: experience navigating a pricing or packaging transition with existing customers; Bonus: SaaS or HR tech background; Bonus: bilingual French–English).

Most of this sounds like you? Apply.

What the job comes with

Base salary: $75k – $85k. 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.
Pay mix: 80% base salary, 20% variable
OTE: $94k–$107k
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.

Note: The internal title for this role is Account Manager.

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.

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