About the role
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 an Account Manager who knows how to build real customer relationships and turn them into lasting partnerships. In this role — an 18-month contract with real impact from day one — you'll own a book of accounts and be responsible for renewing and expanding their value, making sure customers are getting everything they need from Workleap so they want to keep growing with us year after year. You'll be their go-to person: part consultant, part commercial partner, someone who can hold a tough conversation and still come out with a signature.
Your impact:
- Protect and grow a book of accounts by running rigorous renewal conversations that keep GRR on target and create room for NRR expansion ;
- Drive the pricing migration across your accounts — having direct commercial conversations with customers about the move to platform pricing, and closing them ;
- Accelerate multi-module adoption by positioning the Workleap Agent as a force multiplier for managers, not just another product in the stack ;
- Reduce late-stage churn risk by catching warning signals early, escalating with a plan, and running Mid-Term Value Reviews that prove value before the renewal conversation even starts ;
- Maintain a clean, accurate HubSpot pipeline that reflects reality — not optimism — so the team makes the right calls at the right time ;
- Use AI tools (e.g. Claude) to prep for calls, build account briefs, and iterate quickly on outreach — so your time goes toward high-value conversations, not manual research ;
- Help shape the team's playbooks by sharing what you learn and codifying what works, in a team that's actively building its standards after doubling in size.
Your team
You'll be joining a team that takes real pride in winning together. This isn't your typical sales team — we put customers first, which drives a different kind of commercial relationship. The team is high-trust, collaborative, and genuinely invested in each other's growth. You'll be working alongside 8 AMs, 2 CSMs, and 2 Onboarding Managers in a team that's actively building its playbooks after doubling in size.
What's ahead: the pricing migration is one of the most strategic plays of the year — moving legacy customers to the new platform model takes real commercial judgment. On top of that, driving multi-module adoption with customers used to a single-product relationship is a genuine product-selling challenge with a lot of upside. And as a recently expanded team, there's real opportunity to shape how we operate going forward.
What you'll bring
- Bilingual French-English is a must ;
- 2+ years in an AM or CSM role with a renewal quota — you need to have owned a number, not just contributed to one ;
- Experience managing an ARR book in the $1M–$5M range (enough complexity to be relevant, right-sized to translate to our segment) ;
- Proven ability to hold difficult commercial conversations — price increases, pushback, migrations — without losing the relationship or the deal ;
- 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 ;
- Experience in a scale-up or high-growth environment where the playbook is still being written (bonus: experience navigating a pricing or packaging change with existing customers; bonus: player-coach instinct — you share learnings, pull peers up, and build without being asked).
Most of this sounds like you? Apply.
What the job comes with
- Base salary: $80,000–$90,000 CAD + variable. 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. Total on-target earnings (OTE) approximately $115,000–$130,000 CAD ;
- 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 and for us.
Your journey starts with a recruiter conversation, followed by a virtual interview with the hiring manager and one additional interviewer. Next, you'll complete a take-home case study and meet potential teammates to discuss and collaborate on your work. If it's a match on both sides, we move to an offer. Some positions follow a slightly different path — your recruiter will walk you through it on the call if that's the case.
In the spirit of transparency: we use AI to support parts of the process, but every hiring decision remains firmly human.
We're committed to making this an inclusive and thoughtful experience for every candidate. We're looking forward to showing you that.
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