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.