Account Manager - Mid-Market - Workleap (12-month Contract)

Workleap; Montreal (administrative region); Hybrid; CAD 80,000 - 90,000; Full time

Benefits offered by this job

Health insurance

Telemedicine

Annual wellness budget

Flexible vacation

Remote work with Montreal office

In-person gatherings twice a year

Claude access

Job summary

Workleap is seeking an Account Manager in Canada who will own a book of accounts, renewals, and expansion, acting as both consultant and commercial partner. This 12‑month contract role emphasizes strong relationship building and strategic guidance.

The position involves driving multi‑module adoption, managing churn risk, and maintaining a high‑quality HubSpot pipeline while leveraging AI tools to accelerate outreach and insights.

Qualifications

• 2+ years in AM/CSM with renewal quota.
• Experience managing ARR between $1M–$5M.
• Comfort with AI tools (Claude, Copilot, ChatGPT).

Responsibilities

• Renew and expand account value through renewals and upsell.
• Lead pricing migrations and direct commercial conversations.
• Drive multi-module adoption of Workleap Agent.
• Maintain accurate CRM and provide value reviews.

Skills

Account management

Renewal negotiations

CRM hygiene

Forecasting

AI tools usage

Pricing conversations

Job description

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.

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

We're looking for an Account Manager who knows how to build real customer relationships and turn them into lasting partnerships. In this role — 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, somebody who can hold a tough conversation and still come out with a signature. This is a 12‑month contract position.

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

• 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).

What the job comes with

• Base salary: $80k–$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.
• OTE: $115k–$130k
• 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.