Senior Deal Desk Analyst ⭐ at Achievers in Canada

Job description

• 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.

Responsibilities

• 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

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

Skills

Required

• Deal Desk
• Commissions
• Sales Operations
• Revenue Operations
• B2B SaaS
• SaaS pricing models
• Discounting
• Contract structuring
• Deal strategy
• Process optimization
• Automation
• Salesforce (or equivalent CRM)

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
• We’re committed to providing a fair and competitive offer based on what you bring to the team. Each A-Players' compensation is reviewed at least annually against performance and impact in role. We want you to see your path to growth, understand your impact, and feel valued every step of the way.
• $94,000 - $115,000 reflects what we reasonably expect to offer for this role based on current market data. The final offer will depend on several factors, including your skills, experience, and any relevant certifications. As with all market-based ranges, these numbers may evolve over time, but we’re committed to providing a fair and competitive offer based on what you bring to the team.