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.

Your role

ShareGate's Account Management team owns renewals and expansion across our existing customer base and the motion is about to change. Today it runs fast and transactional: a large book, short cycles, high volume. Where we're headed is more deliberate: a segmented renewal motion with real cross-sell revenue built into it. As Manager, Account Management, you own that transition and the team that delivers it.

You'll lead 4–8 Account Managers accountable for GRR, NRR, and expansion. You'll coach on live deals, rebuild the playbook as you go, and stay close enough to the pipeline to know what's actually happening in it. Leading through change means owning the friction your team runs into and being straight with them about what's shifting and why.

This is a builder’s role. If you've run a high-velocity renewal motion and know what it takes to turn it into an expansion engine, this one's for you.

Your impact:

Hit team-level targets across GRR, NRR, and expansion by running a proactive, structured renewal motion instead of reacting at T-90;
Transform a high-velocity renewal team into a segmented, expansion-led one, sequencing the change so throughput holds while the new motion takes root;
Grow cross-sell revenue by leading the ShareGate Protect motion into the existing Migrate base and coaching AMs to open second-product conversations that actually land;
Develop a team of 4–8 Account Managers through weekly 1:1s, pipeline reviews, and live deal coaching that builds skill, not just tracks numbers;
Protect revenue at risk by surfacing churn signals early, coaching save plays, and escalating before a renewal becomes a rescue;
Deliver forecasts leadership can trust, holding the bar on HubSpot pipeline hygiene and using AI to turn CRM data into decisions rather than reports;
Remove friction across the renewal and expansion cycle by partnering with RevOps, Channel, Finance, and Legal on segmentation, reporting, and capacity planning.

Your team

You'll report to the Director, Account Management and inherit a segment of an established team — people who know the book, the customers, and where the current motion strains. Your first job is earning their trust; your second is changing how they work without breaking what already performs.

You'll work closely with Channel, RevOps, Finance, Legal, and HR, and you'll lean on Sales Enablement and Product Marketing to give your team the positioning and talk tracks that make cross-sell conversations feel natural rather than bolted on. The leaders who do best here over-communicate and stay organized, especially when the answer isn't settled yet.

What you'll bring

2+ years leading an Account Management or Customer Success function accountable for both renewal and expansion targets, with a track record of hitting them;
Experience across both ends of the motion — high-velocity transactional renewals and white-glove, strategic accounts — and the judgment to know which one an account needs;
A builder's instinct: you make bets, find out fast whether they worked, and change course in front of your team without losing them;
Strong leadership through change: you over-communicate, own the frustrations your team hits, and stay honest when the answer isn't clear yet;
Strong coaching instincts and radical candor: you can watch a call, name the moment it went sideways, and explain it in a way that sticks;
Working AI fluency: you build workflows and use AI to analyze CRM data and pressure-test decisions, not just to draft emails (HubSpot experience is a plus);
Bonus: familiarity with the Microsoft 365 ecosystem, or experience taking a velocity-driven team through the shift to expansion-led.

Most of this sounds like you? Apply.

What the job comes with

Base salary: $110k to $130k / OTE: $170k–$200k. 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

Manager, Account Management - ShareGate at workleap | AI Job Board