Senior Strategic Account Manager - Workleap

Capital Factory; Montreal (administrative region); On-site; CAD 90,000 - 140,000; Full time

Job summary

Workleap in Montreal is seeking a Senior Account Manager to own a portfolio spanning mid-market to enterprise on the Workleap platform, protecting revenue and driving expansion. You will act as a strategic partner to customers and lead conversations around renewals and pricing migrations to ensure value and retention.

The role requires executive credibility and sound judgment to navigate commercially sensitive discussions while maintaining strong relationships and guiding stakeholders across

Responsibilities

• Own the most complex, highest-ARR accounts in the portfolio by building and maintaining quarterly account plans, mapping stakeholders proactively, and building multi-threaded relationships that survive org changes on the customer side.

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

Workleap's post-sale revenue is scaling - and its most complex accounts need a senior owner who can match the stakes. As a Senior Account Manager, you'll own a portfolio spanning mid-market to enterprise on the Workleap platform: protecting revenue, driving expansion, and acting as a genuine strategic partner to customers. This role exists now because we're executing a pricing migration across the entire book - a commercially sensitive motion that demands executive credibility, sound judgement, and the ability to hold a hard conversation without losing the relationship.

Your impact:

• Own the most complex, highest-ARR accounts in the portfolio by building and maintaining quarterly account plans, mapping stakeholders proactively, and building multi-threaded relationships that survive org changes on the customer side;
• Lead complex renewal negotiations and pricing migration conversations with confidence - knowing when