Caseware is one of Canada’s earliest Fintech innovators, leading the global audit and accounting software market for more than 30 years. Our solutions are used by over 500,000 professionals in 130 countries and are available in 16 languages. Even if you haven’t heard of us yet, more than 36,000 accounting and audit specialists list Caseware as a skill on their LinkedIn profiles.

The Deal Desk Operations Analyst supports the sales team by assessing and operationalizing non-standard deals to ensure they are financially viable, strategically structured, and executable. Working closely with Sales, Client Operations, Pricing, Finance, Legal, and Sales Operations, this role applies pricing guidelines and commercial judgment to balance revenue growth, margin protection, deal speed, and risk mitigation, while maintaining the processes and tools that enable consistent decision-making at scale.

What you will do:
• Assist Sales and Client Operations with structuring, reviewing, and approving non-standard deals with a focus on accuracy and quick turnaround.
• Review pricing, discounts, uplift, margin, and concessions; identify risks and recommend actions.
• Provide guidance based on past deal performance, customer behavior, and pricing precedents; escalate complex cases to the Deal Desk Lead as required.
• Conduct financial analysis to evaluate margin impact, revenue results, and pricing trade-offs across new business, renewals, and expansions.
• Examine historical pricing, uplift, and discount trends to improve deal guidance, margin goals, and pricing frameworks.
• Assess costing data and special costing or deal registration requests to support approvals and process enhancements.
• Refine and maintain deal review and approval workflows to boost consistency, efficiency, and auditability.
• Build and improve deal desk tools and models, such as Excel pricing models, scenario tools, trackers, and templates.
• Identify recurring deal challenges and partner with Sales Operations and Pricing to implement scalable process and tool improvements.
• Collaborate with Finance, Pricing, Legal, Sales Operations, and Client Operations to manage complex deals and secure timely approvals.
• Clearly communicate deal rationale, risks, and recommendations to stakeholders and help align teams on what constitutes a sound deal.
• Apply pricing and approval guidelines while exercising solid commercial judgment and escalating exceptions when needed.
• Monitor deal metrics such as margin impact, discount patterns, approval cycle time, and exceptions, and share actionable insights.
• Support deal and quoting analysis for strategic planning and performance tracking.
• Contribute to documentation, playbooks, and enablement materials that improve sales execution and reduce friction.

What you bring:
• 2–3 years of experience in Deal Desk, Pricing, Finance, Sales Operations, Revenue Operations, Bid Desk, or related fields (3 years preferred).
• Experience supporting B2B pricing in SaaS, subscription, or distribution-based sales models.
• Strong quantitative and financial analysis skills with proven ability to evaluate deal economics and margin implications.
• Advanced Excel skills, including modeling and scenario analysis, and experience with analytics tools; VBA or similar automation skills are strongly preferred.
• Excellent communication and collaboration abilities, with a track record of influencing cross-functional stakeholders.
• Bachelor’s degree in Business, Finance, Economics, Mathematics, or a related discipline (or equivalent experience).

Nice to have:
• Experience working with a centralized Pricing team and exposure to category strategy, cost-to-serve analysis, or margin optimization.
• Familiarity with CRM and CPQ platforms such as Salesforce, Salesforce CPQ, Conga, or Apttus, and experience with quoting workflows.
• Experience improving special costing processes or deal registration programs.
• Experience supporting global or multi-region sales teams and navigating regional policies and approval structures.

What’s in it for you:
• Innovation drives everything we do—we use advanced technology to push the boundaries of accounting and financial reporting software.
• We foster a collaborative culture where ideas are valued and knowledge sharing is encouraged within an inclusive and supportive team.
• We prioritize work-life balance with flexible work options, remote opportunities, and generous time-off policies.
• We offer competitive compensation, including salary, health benefits, and retirement plans.
• Your work has real impact, shaping how clients manage financial processes and achieve success.
• We value recognition and reward high performance through acknowledgment programs, bonuses, and career growth opportunities.
• You will have opportunities to work on global initiatives and collaborate with a diverse international team.

About Caseware:
Caseware designs advanced software for accounting firms, corporations, and government organizations. Our teams constantly collaborate and innovate to enhance our product suite. With a customer-first approach, we are building the future of audits, financial reporting, and financial data analytics.

Following a strategic investment from Hg Capital in 2020, Caseware is entering its next phase of major growth, expanding the people and products that have driven our success.

We are committed to diversity, equity, and inclusion through our core value of Many Voices, One Team. We welcome applicants from all backgrounds. If you need accommodations or have questions at any stage of the hiring process, please contact our People Operations team at talent@caseware.com.

Background Check:
Candidates who receive an offer will be required to complete a background check through https://certn.co, which generally includes identity verification and a criminal record check. Executives and Senior Managers will also undergo a soft credit check. Candidates in the Netherlands and Germany are not required to complete checks through Certn.

Security and Fraud:
Caseware takes candidate security seriously. All legitimate communication from us will come from email addresses ending in @caseware.com, and our open roles are always listed on reputable job boards and our website. We will never request payment or financial information. If you receive an unsolicited job offer, proceed with caution.