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 new business, expansion, andrenewal dealsLead complex and non-standard deals, providing strategic guidance on pricing, licensingmodels, and commercial constructsPartner 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 approvalstepProvide clear guidance and transparency on pricing, approvals, and deal structures to helpSales and Customer Success navigate trade-offs and drive more efficient deal executionApply sound judgment to balance sales velocity with pricing integrity, margin protection, andlong-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 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 recommendationsAct as a subject matter expert (SME) for deal structuring, pricing strategy,



and contractingbest practices across the organizationMentor and support Deal Desk Analysts, sharing subject matter expertise and elevating teamcapability, consistency, and judgmentDefine and evolve pricing frameworks, discount matrices, approval governance, and dealguardrailsBuild, document, and standardize Deal Desk processes, playbooks, and operating proceduresto drive consistency, clarity, and scalabilityIdentify and implement opportunities for process optimization, automation, and workflowimprovements to reduce manual effort and increase efficiencyStreamline deal approval and contract workflows to accelerate deal cycle times whilemaintaining appropriate controls and complianceDevelop reporting and dashboards to track deal performance, discounting trends, andoperational effectivenessEnable Sales and Customer Success teams through training and ongoing guidance onpricing, deal structuring, tools, and processes, empowering teams to structure stronger dealsupfrontFoster a culture of continuous improvement, balancing collaboration and responsivenesswith 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 Operationswithin a B2B SaaS environmentProven ability to operate in a high-volume, hands-on deal environment while contributingstrategically 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/automationsystemsAdvanced Excel or Google Sheets skills with strong analytical and data interpretationcapabilitiesExcellent communication and stakeholder management skills, with the ability to influencewithout direct authorityDemonstrated ability to balance a collaborative, solution-oriented approach with adherenceto business policies, guardrails,



and operational consistencyStrong attention to detail and ability to manage competing priorities in a fast-pacedenvironmentWhy Achievers is a Great Place to Work
At 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 Rewards
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.Perks and Perks for permanent full-time employees:
Rewardsfor your impact through our Recognition and Rewards programHealthBenefits and Life Insurance Coverage beginning on your first dayParentalLeave Top-upEmployer matched RRSPcontributionsFlexibleVacation to recharge, so you can bring your bestEmployeeand Family Assistance Programoffering mental health, legal, and financial counsellingSupportedprofessional development and career growth(Linkedin Learning, mentorship)Employee-Led Employee Resource Groupsthat celebrate our diversityRegular events designed to build connection, belonging, and well-beingHybridflexibility, 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 (Winnipeg)
🏢 Achievers
📍 Winnipeg