Senior Strategic Account Manager - Workleap

Location: Montreal

# Senior Strategic Account Manager - Workleap Workleap Remote Canada Customer  Support & Success Posted Oct 16, 2026

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 Share Gate, 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 judgment, 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 to hold the commercial line and when flexibility is the right call, including through procurement and legal;

• Drive expansion from demonstrated value: use usage data and outcome metrics to build an ROI story customers can articulate in their own words, and initiate expansion conversations at six months — not eleven;

• Handle executive escalations with composure by documenting clear save plans, flagging risk before it surfaces reactively, and keeping the internal team aligned when accounts go sideways;

• Use AI tools (Claude, ChatGPT, or equivalent) daily to prepare for customer conversations, synthesize account data, draft renewal strategies, and move faster across a complex book — a habit, not a checkbox;

• Raise the team's floor by modeling strong account management habits — how to run a quarterly plan, how to prep an executive Q , how to navigate a tough objection — so that junior team members grow through proximity;

• Give leadership a reliable, real-time view of the portfolio by maintaining CRM as a live document, with documented next steps on expansion pipeline and active mitigation plans on at-risk accounts.
Your team    You're joining a structured, systems-oriented AM/CSM team where autonomy is expected and operational rigor is non-negotiable.
Two Customer    Success    Managers share the portfolio with you; cross-functional collaboration with Product, Finance, and Legal is part of the job on complex accounts.
The team doesn't run on heroics or tribal knowledge — it runs on clear plans, a live CRM, and a predictable cadence.
This year's challenge: execute the pricing migration across the full book, build executive multi-threading in accounts that are currently too single-threaded, and operate with more leverage without adding headcount.
The senior person in this team sets the standard everyone else follows.
What you'll bring    
• 4+ years in SaaS account management or customer success, with direct experience on enterprise or upper mid-market accounts;

• Consistent track record of meeting or exceeding NRR targets in complex books, including…