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.This is a 12 month contract position.How you'll own the Deal Desk function at Achievers: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 dealsLead complex and non‑standard deals, providing strategic guidance on pricing, licensing models, and commercial constructsPartner 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 stepProvide clear guidance and transparency on pricing, approvals, and deal structures to help Sales and Customer Success navigate trade‑offs and drive more efficient deal executionApply sound judgment to balance sales velocity with pricing integrity, margin protection, and long‑term revenue outcomesAct as the primary liaison between Sales, Legal, and Finance to align on contract terms, approvals, and deal strategySupport 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 outcomesServe as an escalation point for high‑impact or non‑standard deals, providing explicit and data‑driven recommendationsAct as a subject‑matter expert (SME)



for deal structuring, pricing strategy, and contracting best practices across the organizationMentor and support Deal Desk Analysts, sharing subject‑matter expertise and elevating team capability, consistency, and judgmentDefine and evolve pricing frameworks, discount matrices, approval governance, and deal guardrailsBuild, document, and standardize Deal Desk processes, playbooks, and operating procedures to drive consistency, clarity, and scalabilityIdentify and implement opportunities for process optimization, automation, and workflow improvements to reduce manual effort and increase efficiencyStreamline deal approval and contract workflows to accelerate deal cycle times while maintaining appropriate controls and complianceDevelop reporting and dashboards to track deal performance, discounting trends, and operational effectivenessEnable Sales and Customer Success teams through training and ongoing guidance on pricing, deal structuring, tools, and processes, empowering teams to structure stronger deals upfrontFoster a culture of continuous improvement, balancing collaboration and responsiveness with strong operational discipline, accountability, and consistencyExperience we feel will set you up for success:6+ years of experience in Deal Desk, Commissions, Sales Operations, or Revenue Operations within a B2B SaaS environmentProven ability to operate in a high‑volume, hands‑on deal workplace while contributing strategically as a subject‑matter expertStrong expertise in SaaS pricing models, discounting, contract structuring, and deal strategyExperience building, documenting, and optimizing scalable processes and workflowsDemonstrated experience driving process improvements and automation initiativesStrong cross‑functional collaboration experience with Sales, Customer Success, Legal, Finance, and related stakeholdersProficiency with Salesforce (or equivalent CRM), CLM tools, and workflow/automation systemsAdvanced Excel or Google Sheets skills with strong analytical and data interpretation capabilitiesExcellent communication and stakeholder management skills, with the ability to influence without direct authorityDemonstrated ability to balance a collaborative,



solution‑oriented approach with adherence to business policies, guardrails, and operational consistencyStrong attention to detail and ability to manage competing priorities in a fast‑paced environmentWhy Achievers is a Great Place to WorkAt Achievers, we believe recognition is a powerful driver of connection. With more than 4.3 million users across 190 countries, our employee recognition and rewards platform empowers organizations to build cultures where people feel seen and valued, everyday. We’re a team of passionate, thoughtful builders who care deeply about our product, our customers, and each other. Visit achievers.Com to see how we’re inspiring recognition everywhere.Our Approach to Total RewardsWe’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.Benefits and Perks for permanent full‑time employeesRewards for your impact through our Recognition and Rewards programEmployee and Family Assistance Program offering mental health, legal, and financial counsellingSupported professional development and career growth (LinkedIn Learning, mentorship)Employee‑Led Employee Resource Groups that celebrate our diversityRegular events designed to build connection, belonging, and well‑beingHybrid flexibility, with time in our beautiful Liberty Village, Toronto officeAchievers is proud to be an equal opportunity employer committed to building a diverse, inclusive workplace where everyone can do their best work. We encourage qualified candidates from all backgrounds and experiences to apply.Achievers is committed to ensuring an inclusive and accessible recruitment process for all candidates. If you require any accommodations for your interview, such as assistive technology, wheelchair accessibility, or alternative formats of materials, please let us know. We are happy to make necessary arrangements to support your needs.#J-18808-Ljbffr

📌 Senior Deal Desk Analyst - $94,000 - $115,000 A Year (Winnipeg)
🏢 Achievers
📍 Winnipeg