Senior Strategic Account Manager - Workleap

Accountabilities Own a portfolio of complex, high-ARR mid-market and enterprise accounts, developing quarterly account plans and proactive stakeholder maps.

Build multi-threaded relationships across customer organizations, including executive, procurement, legal, and operational stakeholders.

Lead complex renewal negotiations and pricing migration discussions, balancing commercial objectives with long-term customer relationships.

Identify expansion opportunities by using product usage, customer outcomes, and ROI insights to demonstrate additional value.

Initiate expansion conversations proactively and build strategies that support sustainable account growth.

Manage executive escalations with clear save plans, early risk identification, and coordinated internal action.

Use AI tools such as Claude, ChatGPT, or equivalent solutions to prepare for customer conversations, analyze account information, develop strategies, and improve productivity.

Maintain accurate, actionable CRM records, including expansion opportunities, next steps, renewal plans, and mitigation strategies for at-risk accounts.

Partner with Customer Success, Product, Finance, Legal, and other teams to deliver coordinated solutions for complex accounts.

Mentor and support less experienced team members by sharing practical approaches to account planning, executive QBRs, objection handling, and strategic customer management.

Requirements

4+ years of experience in SaaS account management or customer success, with direct responsibility for enterprise or upper mid-market customers.

Demonstrated experience meeting or exceeding net revenue retention (NRR) targets across complex customer portfolios.

Proven ability to manage renewals involving procurement, legal, and other senior stakeholders.

Strong executive relationship-management skills, with experience building multi-threaded customer relationships rather than relying on a single internal champion.

Strong commercial and negotiation skills, including the ability to navigate pricing changes, packaging changes, and sensitive customer conversations.

Highly disciplined approach to CRM management, treating customer and opportunity data as an active source of operational insight.

Daily experience using AI tools for meeting preparation, account research, information synthesis, and workflow acceleration.

Fluent French and English, both written and spoken.

Strong organizational skills and the ability to operate with autonomy while maintaining rigorous processes and follow-through.

Excellent communication, judgment, problem-solving, and relationship-building abilities.

Experience in SaaS HR technology or familiarity with HR, People Operations, and C-suite buyers is an asset.

Experience managing pricing migrations or significant packaging changes with existing customers is an asset.

Benefits

Base salary of $100,000–$120,000 CAD .

On-target earnings of $170,000–$200,000 CAD .

Compensation is based on a Canada-wide scale, with final offers potentially adjusted according to regional market conditions.

Long-term incentive program providing an opportunity to participate in long-term company growth.

RRSP program.

Family health insurance.

Telemedicine services.

Annual wellness budget.

Flexible vacation policy.

Remote-first work model with access to a Montreal office.

In-person team gatherings twice per year.

Access to Claude for all employees.

A collaborative, systems-oriented environment with opportunities to influence account management practices and support team development.

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