Senior Deal Desk Analyst

Achievers

Senior Analyst, Deal Desk at Achievers evolving the Deal Desk function. Collaborate with Sales, Customer Success, Legal, and Finance to optimize deal processes and enhance revenue outcomes.

Posted 5/30/2026contractToronto • 🇨🇦 CanadaSenior💰 $94,000 - $115,000 per yearWebsite

About the role

Key responsibilities & impact

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 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

Requirements

What you’ll need

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

Benefits

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

deal structuringpricing strategycontract structuringSaaS pricing modelsdiscountingprocess optimizationautomation initiativesdata interpretationanalytical skillsworkflow improvements

Soft Skills

communication skillsstakeholder managementcollaborationinfluence without authorityattention to detailsolution-oriented approachoperational disciplineaccountabilitymentoringcontinuous improvement