Senior Manager, Sales Compensation and Deal Desk

Role Overview

• Lead high-impact initiatives that shape how millions of people experience work around the world.
• Bring your unique perspective to complex and challenging projects
• apply your expertise in data science, influence technical direction, and share your knowledge with fellow team members.
• Join a close-knit, no-ego, high-performing team that solves meaningful problems and celebrates successes together.
• Work alongside an experienced leadership team who is genuinely invested in your career growth.
• Thrive in a fast-paced, high-growth environment where innovation is encouraged and your voice truly matters.
• Partner with Finance and Sales leadership to design and operationalize sales compensation plans aligned to business goals.
• Support the ongoing management, analysis, and optimization of incentive programs.
• Lead communication and enablement related to compensation policies.
• Apply rigorous attention to detail when managing commission data, owning the end-to-end process while minimizing errors and adhering to the structure of the plans.
• Own Salesforce effectiveness metrics and collaborate with Enablement and HR to identify performance gaps and improve overall sales team effectiveness.
• Drive automation and tooling enhancements to support scale and efficiency, leveraging AI to improve efficiency.
• Own and lead global Deal Desk operations, ensuring efficiency, compliance, and strategic deal execution.
• Serve as the escalation point for complex deal structuring and pricing questions.
• Define and maintain Grants of Authority (GOA) and pricing threshold documentation and ensure clear communication across GTM teams. Lead enablement of Achievers pricing and sales process.
• Maintain Deal Desk Playbook documenting company’s position on critical terms and conditions, including GOA, in collaboration with Legal and Finance.
• Collaborate with Legal, Finance, and Sales to resolve deal issues and streamline approvals.
• Manage the Deal Desk Dictionary and enablement efforts across revenue teams.
• Create complex pricing proposals with minimal oversight; deliver pricing insights to senior leadership.
• Lead, coach, and develop a team across Commissions and Deal Desk.
• Drive cross-functional alignment on strategic initiatives, GTM motions, and operational enhancements.
• Ensure clear and streamlined operating mechanisms between Revenue teams and internal teams.

Requirements

• Strategic Communication: Ability to tailor complex messages for different audiences, including executives, sales teams, and cross-functional stakeholders, to drive alignment and clarity in decision-making.
• Stakeholder Influence & Relationship Management: Proven track record of building and sustaining strong partnerships across Sales, Finance, Legal, and Product to support scalable revenue growth and deal execution.
• Accountability & Ownership: Demonstrates a high level of ownership, driving initiatives from conception to execution with minimal oversight.
• Process Leadership: Expertise in managing and scaling operational processes, driving continuous improvement across workflows.
• Confident Decision-Making: Exercises sound judgment in high-stakes scenarios and clearly communicates rationale to both peers and senior leadership.
• Team Leadership & Enablement: Experience leading teams or mentoring others, removing roadblocks, and fostering a high-performance culture within a revenue or operations environment.
• Deal Structuring & Negotiation: Adept at managing strategic deal negotiations independently, including pricing, terms, and redlines, while supporting junior team members in skill development.
• Commercial & Pricing Strategy Execution: Capable of optimizing deal structures for long-term customer value and profitability, with a demonstrated ability to lead enterprise pricing strategy conversations.
• Risk & Compliance Management: Skilled at identifying risks in non-standard deals and implementing frameworks to mitigate financial and operational exposure.
• Operational Innovation: Leads initiatives to automate and streamline internal deal desk processes to enhance efficiency and scalability.
• Escalation Leadership: Serves as a trusted escalation point for commissions and deal related issues, resolving conflicts swiftly and effectively with cross-functional stakeholders.

Benefits

• Rewards for your impact through our Recognition and Rewards program
• Health Benefits and Life Insurance Coverage beginning on your first day
• Parental Leave Top-up
• Employer matched RRSP contributions
• Flexible Vacation to recharge, so you can bring your best
• Employee and Family Assistance Program offering mental health, legal, and financial counselling
• Supported professional development and career growth (Linkedin Learning, mentorship)
• Employee-Led Employee Resource Groups that celebrate our diversity
• Regular events designed to build connection, belonging, and well-being
• Hybrid flexibility, with time in our beautiful Liberty Village, Toronto office