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Salary: CAD 94,000 - 115,000 / annual
Achievers is seeking a Senior Deal Desk Analyst to evolve and mature the Deal Desk function. This is a hands-on individual contributor role combining 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 building frameworks, guardrails, and processes that create consistency and scale. You will balance strong collaboration and commercial flexibility with clear standards and operational rigor.
Key responsibilities include:
- 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 compliant deals, acting as a thought partner
- Provide clear guidance and transparency on pricing, approvals, and deal structures
- 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
- Serve as an escalation point for high-impact or non-standard deals, providing clear and data-driven recommendations
- Act as a subject matter expert for deal structuring, pricing strategy, and contracting best practices
- Mentor and support Deal Desk Analysts, sharing subject matter expertise and elevating team capability
- Define and evolve pricing frameworks, discount matrices, approval governance, and deal guardrails
- Build, document, and standardize Deal Desk processes, playbooks, and operating procedures
- Identify and implement opportunities for process optimization, automation, and workflow improvements
- Streamline deal approval and contract workflows to accelerate deal cycle times while maintaining 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
- Foster a culture of continuous improvement, balancing collaboration and responsiveness with operational discipline and accountability
Achievers is an employee recognition and rewards platform with more than 4.3 million users across 190 countries. The company offers hybrid flexibility with time in the Toronto office (Liberty Village).
REQUIREMENTS:
- 6+ years of experience in Deal Desk, Commissions, Sales Operations, or Revenue Operations within a B2B SaaS environment
- Proven ability to operate in a high-volume, hands-on deal environment while contributing strategically as a subject matter expert
- Strong expertise in SaaS pricing models, discounting, contract structuring, and deal strategy
- Experience building, documenting, and optimizing scalable processes and workflows
- Demonstrated experience driving process improvements and automation initiatives
- Strong cross-functional collaboration experience with Sales, Customer Success, Legal, Finance, and related stakeholders
- Proficiency with Salesforce (or equivalent CRM), CLM tools, and workflow/automation systems
- Advanced Excel or Google Sheets skills with strong analytical and data interpretation capabilities
- Excellent communication and stakeholder management skills, with the ability to influence without direct authority
- Demonstrated ability to balance a collaborative, solution-oriented approach with adherence to business policies, guardrails, and operational consistency
- Strong attention to detail and ability to manage competing priorities in a fast-paced environment
