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

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. 

▪️We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team. 

▪️Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance. 

▪️We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans. 

▪️We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success. 

▪️Recognition and rewards matter to us. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth. 

▪️We embrace global opportunities. Work on international projects and collaborate with a diverse, global team. 

About Caseware:

Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products. With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like.

With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.

One of Caseware's core values is Many Voices, One Team and with that in mind, we're dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at talent@caseware.com.

Background Check:

Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co 

Security and Fraud:

Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.