Deal Desk Operations Analyst

CaseWare International; Remote; CAD 60,000 - 80,000; Full time

Job summary

A leading Fintech company in Canada is seeking a Deal Desk Operations Analyst who will support the sales organization by evaluating and operationalizing non-standard deals. The role requires strong quantitative and financial analysis skills, and candidates should have 2-3 years of relevant experience in Deal Desk, Pricing, or Sales Operations. This position offers a collaborative culture, work-life balance, competitive compensation, and opportunities for international projects.

Benefits

Health insurance

Retirement plans

Flexible work options

Performance bonuses

Generous time-off policies

Qualifications

• 2-3 years of experience in Deal Desk or similar roles.
• Experience supporting B2B pricing in SaaS or subscription models.
• Advanced Excel skills with experience in automation preferred.

Responsibilities

• Support Sales in structuring non-standard deals.
• Conduct financial analyses to assess margin impacts.
• Develop and maintain deal desk tools and models.

Skills

Quantitative analysis

Financial analysis

Communication skills

Collaboration

Excel modeling

Education

Bachelor's degree in Business or related field

Tools

Salesforce

Excel

VBA

Job description

Overview

Caseware is one of Canada's original Fintech companies, with over 30 years leading the global audit and accounting software industry. We serve more than 500,000 users across 130 countries and 16 languages. More than 36,000 accounting and audit professionals list Caseware as a skill on LinkedIn.

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 processes and tools that scale consistent decision-making.

What you will do

• 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.
• 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.
• 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.
• 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.
• 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.

Qualifications

• 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).

Nice to have

• 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.

What’s in it for you

Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions.

Collaborative culture. Your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team.

Work-life balance. Flexible work options, remote opportunities, and generous time-off policies.

Competitive compensation. Competitive salary and comprehensive benefits including health insurance and retirement plans.

Impactful work. Your contributions directly affect how clients manage financial processes and drive their success.

Recognition and rewards. Recognition programs, performance bonuses, and opportunities for career growth.

Global opportunities. Work on international projects and collaborate with a diverse, global team.

About Caseware

Caseware's cutting-edge software products are designed for accounting firms, corporations, and governments. Our teams collaborate, innovate, and build on our suite of products with a customer-focused mindset for the future of audits, financial reporting, and data analytics.

With a recent strategic investment from Hg Capital in 2020, Caseware is in a growth phase focused on people and products that have driven our success to date.

Caseware values Many Voices, One Team and welcomes candidates from all backgrounds. We are committed to diversity, equity, and inclusion. If you require accommodations or have questions during the application or interview process, please email [e-mail].

Background Check

Candidates offered a position will complete a background check through Certn.co, typically including Identity Verification and Criminal Record Check. Executives and Senior Managers may undergo a Soft Credit Check. Candidates residing in the Netherlands and Germany are excluded from Certn.co checks.

Security and Fraud

Caseware takes candidate security seriously. All legitimate communications from us will come from @caseware.com email addresses. Our open positions are listed on reputable job boards and on our website. We will never ask for payment or financial information. If you receive an unsolicited job offer, proceed with extreme caution.