Deal Desk Operations Analyst

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles! The Deal Desk Operations Analyst supports the sales organization by evaluating and operationalizing non-standard deals to ensure they are financially sound, strategically structured, and executable. Partnering with Sales, Client Operations, Pricing, Finance, Legal, and Sales Operations, this role applies pricing guardrails and commercial judgment to balance revenue growth, margin protection, deal velocity, and risk management while maintaining the processes and tools that scale consistent decision-making. What you will be doing: * Deal Evaluation and Sales Support * Support Sales and Client Operations in structuring, reviewing, and approving non-standard deals with a focus on speed and accuracy. * Perform deal reviews covering pricing, discounting, uplift, margin, and concessions; document risks and recommend actions. * Provide guidance using historical deal performance, customer patterns, and pricing precedents; escalate complex scenarios to the Deal Desk Lead as needed. Pricing and Financial Analysis * Conduct financial analyses to assess margin impact, revenue outcomes, and pricing trade-offs across new business, renewal, and expansion motions. * Analyze historical pricing, uplift, and discounting trends to strengthen deal guidance, margin targets, and pricing frameworks. * Evaluate costing data and special costing or deal registration requests to support approvals and process improvements. Process, Tooling, and Operational Excellence * Operationalize and continuously improve deal review and approval workflows to increase consistency, efficiency, and auditability. * Develop, enhance, and maintain deal desk tools and models (e.g., Excel-based pricing models, scenario tools, workflow trackers, and templates). * Identify recurring deal issues and partner with Sales Operations and Pricing to implement scalable process or tooling fixes. Cross-Functional Collaboration and Governance * Interface with Finance, Pricing, Legal, Sales Operations, and Client Operations to manage complex deals and drive timely approvals. * Communicate deal rationale, risks, and recommendations clearly to stakeholders and help align teams on what constitutes a "good deal". * Enforce pricing and approval guardrails while applying sound commercial judgment and escalating exceptions appropriately. Reporting, Insights, and Enablement * Track deal metrics (e.g., margin impact, discounting trends, approval cycle time, exception frequency) and surface actionable insights. * Support deal and quoting analyses for strategic planning and performance tracking. * Contribute to documentation, playbooks, and enablement materials that reduce friction and strengthen sales execution. What you bring: * 2-3 years of experience in Deal Desk, Pricing, Finance, Sales Operations, Revenue Operations, Deal/Bid Desk, or similar roles (3 years preferred). * Experience supporting B2B pricing in SaaS, subscription, or distribution-based sales models. * Strong quantitative and financial analysis skills with demonstrated ability to assess deal economics and margin impact. * Advanced Excel skills (modeling and scenario analysis) and experience with analytics tools; VBA or similar automation experience strongly preferred. * Strong communication and collaboration skills with proven ability to work cross-functionally and influence stakeholders. * Bachelor's degree in Business, Finance, Economics, Mathematics, or a related field (or equivalent experience). * Experience working closely with a centralized Pricing team and exposure to category strategy, cost-to-serve, or margin optimization. * Familiarity with CRM and CPQ systems (e.g., Salesforce, Salesforce CPQ, Conga, Apttus) and quoting workflows. * Experience improving special costing processes and/or deal registration programs. * Experience supporting global or multi-region sales teams and navigating differing regional policies or approval requirements. Perks and Benefits * ¨Contrato a termino Indefinido¨ with all the legal benefits * Prepaid Medicine * Life insurance and funeral assistance * Internet allowance * Home office stipend * Competitive compensation — above the market average * 100% remote work environment and an excellent work-life balance * Opportunity to work for a growing global SaaS leader company * A culture that promotes independence, innovation, trust, and accountability * Open space to be creative, innovative and strategize for the future * Mentorship by highly experienced professional * Budget for training, we want you to grow * 5 Personal Time Off days per year * Sick Leave Top up to total 100% of salary paid by the employer from Day 3 to 90. * Recognition Award, additional paid time off in recognition of the corresponding year of service * Upgrade vacation starting at 5 years of service