Senior Strategic Account Manager

Workleap

. 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 .

Posted 9/28/2026full-timeRemote • CanadaSenior💰 CA$100,000 - CA$120,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in SaaS account management with a focus on enterprise and upper mid-market accounts, leveraging AI tools for strategic planning and stakeholder engagement. Proven ability to drive renewals and expansions through data-driven insights and strong relationship management.

Highest-signal resume keywords

SaaS Account ManagementExecutive Stakeholder ManagementCRM DisciplineBilingual French-EnglishAI Tools Utilization

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Renewal NegotiationPricing MigrationAccount PlanningUsage Data AnalysisOutcome Metrics

Soft Skills

Relationship BuildingCross-Functional CollaborationRisk ManagementProblem Solving

Tools & Technologies

ClaudeChatGPTCRM Software

Industry Keywords

SaaSCustomer SuccessEnterprise AccountsUpper Mid-Market AccountsHR Tech

About the role

Key responsibilities & 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, including through procurement and legal
Drive expansion from demonstrated value using usage data and outcome metrics to build an ROI story, and initiate expansion conversations at six months
Handle executive escalations by documenting clear save plans, flagging risk before it surfaces reactively, and keeping the internal team aligned
Use AI tools such as Claude or ChatGPT daily to prepare for customer conversations, synthesize account data, draft renewal strategies, and move faster across a complex book
Model strong account management habits, including quarterly planning, executive QBR preparation, and navigating tough objections
Maintain CRM as a live document with documented next steps on expansion pipeline and active mitigation plans on at-risk accounts
Collaborate cross-functionally with Product, Finance, and Legal
Provide leadership with a reliable, real-time view of the portfolio

Requirements

What you’ll need

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

Benefits

Comp & perks

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