Senior Strategic Account Manager - Workleap

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 QBR, 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 renewals involving procurement and legal stakeholders;
• Proven executive stakeholder management — multi-threaded relationships, not just the day-to-day champion;
• Rigorous CRM discipline: you treat CRM as a live document, not a reporting obligation;
• Daily use of AI tools (Claude, ChatGPT, or equivalent) for meeting prep, account research, and synthesis — a genuine work habit, not something you're exploring;
• Bilingual French-English (written and spoken);
• Bonus: SaaS HR tech experience, or familiarity with HR, People Ops, and C-suite buyers;
• Bonus: experience navigating a pricing migration or major packaging change with existing customers.

Most of this sounds like you? Apply.

What the job comes with

• Base salary: $100k - $120k / 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.