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.

How you'll own the Deal Desk function at Achievers:

- Own and execute day-to-day Deal Desk support, including managing deal reviews, pricingrequests, discount approvals, and contract structuring across current business, expansion, andrenewal deals
- Lead complex and non-standard deals, providing strategic guidance on pricing, licensingmodels, and commercial constructs
- Partner with Sales and Customer Success to structure competitive, scalable, and compliandeals, acting as a thought partner to drive the right deal outcomes—not simply an approvalstep
- Provide clear guidance and transparency on pricing, approvals,



and deal structures to helpSales and Customer Success navigate trade-offs and drive more efficient deal execution
- Apply sound judgment to balance sales velocity with pricing integrity, margin protection, andlong-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 tocrediting validation, exception review, and payout accuracy, stepping in during peak periodsor planned absences and applying Deal Desk judgment to ensure consistent, compliantcompensation 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 contractingbest practices across the organization
- Mentor and support Deal Desk Analysts, sharing subject matter expertise and elevating teamcapability, consistency, and judgment
- Define and evolve pricing frameworks, discount matrices, approval governance, and dealguardrails
- Build, document, and standardize Deal Desk processes, playbooks, and operating proceduresto drive consistency, clarity, and scalability
- Identify and implement opportunities for process optimization, automation,



and workflowimprovements to reduce manual effort and increase efficiency
- Streamline deal approval and contract workflows to accelerate deal cycle times whilemaintaining appropriate controls and compliance
- Develop reporting and dashboards to track deal performance, discounting trends, andoperational effectiveness
- Enable Sales and Customer Success teams through training and ongoing guidance onpricing, deal structuring, tools, and processes, empowering teams to structure stronger dealsupfront
- Foster a culture of continuous improvement, balancing collaboration and responsivenesswith strong operational discipline, accountability, and consistency

Experience we feel will set you up for success:

- 6+ years of experience in Deal Desk, Commissions, Sales Operations, or Revenue Operationswithin a B2B SaaS environment
- Proven ability to operate in a high-volume, hands-on deal environment while contributingstrategically 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/automationsystems
- Advanced Excel or Google Sheets skills with strong analytical and data interpretationcapabilities
- Excellent communication and stakeholder management skills, with the ability to influencewithout direct authority
- Demonstrated ability to ba

📌 Senior Deal Desk Analyst (Toronto)
🏢 Achievers
📍 Toronto