Senior Deal Desk Analyst

• We are seeking a strategic and execution-focused Senior Analyst, Deal Desk to help evolve and mature our Deal Desk function
• This is a hands-on individual contributor role that combines day-to-day deal execution with subject matter expertise and functional ownership
• You will operate as both a player and a builder—owning deal desk ticket execution and complex deal support while driving process optimization, automation, and scalable improvements
• You will partner closely with Sales, Customer Success, Legal, and Finance to structure high-quality deals across land, expand, and renewal motions, directly impacting ARR growth, deal velocity, and long-term customer value
• You will enable efficient deal progression while also building the frameworks, guardrails, and processes that create consistency and scale
• You will balance strong collaboration and commercial flexibility with clear standards and operational rigor, ensuring deals support both immediate revenue objectives and sustainable growth, while reducing friction in the deal process by improving upfront clarity and enabling stronger deal structuring at the source
• Own and execute day-to-day Deal Desk support, including managing deal reviews, pricing requests, discount approvals, and contract structuring across new business, expansion, and renewal deals
• Lead complex and non-standard deals, providing strategic guidance on pricing, licensing models, and commercial constructs
• Partner with Sales and Customer Success to structure competitive, scalable, and complian deals, acting as a thought partner to drive the right deal outcomes—not simply an approval step
• Provide clear guidance and transparency on pricing, approvals, and deal structures to help Sales and Customer Success navigate trade-offs and drive more efficient deal execution
• Apply sound judgment to balance sales velocity with pricing integrity, margin protection, and long-term revenue outcomes
• Act as the primary liaison between Sales, Legal, and Finance to align on contract terms, approvals, and deal strategy
• Support commissions processes during monthly and quarterly cycles by contributing to crediting validation, exception review, and payout accuracy, stepping in during peak periods or planned absences and applying Deal Desk judgment to ensure consistent, compliant compensation outcomes
• Serve as an escalation point for high-impact or non-standard deals, providing clear and data-driven recommendations
• Act as a subject matter expert (SME) for deal structuring, pricing strategy, and contracting best practices across the organization
• Mentor and support Deal Desk Analysts, sharing subject matter expertise and elevating team capability, consistency, and judgment
• Define and evolve pricing frameworks, discount matrices, approval governance, and deal guardrails
• Build, document, and standardize Deal Desk processes, playbooks, and operating procedures to drive consistency, clarity, and scalability
• Identify and implement opportunities for process optimization, automation, and workflow improvements to reduce manual effort and increase efficiency
• Streamline deal approval and contract workflows to accelerate deal cycle times while maintaining appropriate controls and compliance
• Develop reporting and dashboards to track deal performance, discounting trends, and operational effectiveness
• Enable Sales and Customer Success teams through training and ongoing guidance on pricing, deal structuring, tools, and processes, empowering teams to structure stronger deals upfront
• Foster a culture of continuous improvement, balancing collaboration and responsiveness with strong operational discipline, accountability, and consistency

Benefits

• Parental Leave Top-up
• RRSP Matching
• Health Benefits and Life Insurance Coverage Upon Your First Day
• Flexible Vacation
• Employee and Family Assistance Program
• Full access to the LinkedIn Learning Library
• Internal Mentorship Program
• Employee-Led Employee Resource Groups
• Participation in our Points-based Employee Recognition Program
• A beautiful office space located in Liberty Village, Toronto
• Opportunities for professional development and career growth

Proven ability to operate in a high-volume, hands-on deal environment while contributing strategically as a subject matter expertFinance, and related stakeholders6+ years of experience in Deal Desk, Commissions, Sales Operations, or Revenue Operations within a B2B SaaS environmentDemonstrated ability to balance a collaborative, solution-oriented approach with adherence to business policies, guardrails, and operational consistencyExperience building, documenting, and optimizing scalable processes and workflowsExcellent communication and stakeholder management skills, with the ability to influence without direct authorityAdvanced Excel or Google Sheets skills with strong analytical and data interpretation capabilitiesProficiency with Salesforce (or equivalent CRM), CLM tools, and workflow/automation systemsDemonstrated experience driving process improvements and automation initiativesStrong cross-functional collaboration experience with Sales, Customer Success, Legal,Strong expertise in SaaS pricing models, discounting, contract structuring, and deal strategyStrong attention to detail and ability to manage competing priorities in a fast-paced environment