Senior Commercial Deal Desk Analyst

Overview

This role supports the growth and scaling of a Commercial Deal Desk capability within Revenue Operations. You will partner with Sales, Finance, Legal, and cross-functional teams to help drive complex commercial decisions and turn insights into repeatable processes, guidance, and tools that enable faster, confident execution as deal complexity and volume increase.

Reporting to the Senior Manager, Deal Desk, this is a remote role based in North America, supporting teams across the United States and Canada.

Responsibilities

• Partner with Enterprise Account Executives (AEs), Sales Managers, Finance, Legal, and Revenue Operations on complex, non-standard, and high-impact deals.
• Advise on deal structure, pricing, terms, discounting, approvals, amendments, renewals, co-terms, ramps, bundled products, and related commercial considerations.
• Review and execute deal submissions in Salesforce CPQ/Revenue Cloud, ensuring quotes and contracts are accurate, complete, and ready for approval and invoicing.
• Build and strengthen the Commercial Deal Desk foundation, including intake processes, approval routing, discount governance, exception handling, service-level agreements (SLAs), and documentation.
• Create playbooks, training materials, office hours, and practical guidance to help sales teams navigate commercial processes and quoting tools.
• Identify opportunities to improve workflows through automation, AI tooling, and CPQ configuration, coordinating with technical teams on scalable implementations.
• Use deal data and Key Performance Indicators (KPIs) to identify bottlenecks, improve deal quality, and recommend changes that support efficient, sustainable growth.

Requirements

• 4+ years of experience in Deal Desk, Revenue Operations, Commercial Finance, or a related function within a Business-to-Business (B2B) Software as a Service (SaaS) environment.
• Hands-on experience with Salesforce Customer Relationship Management (CRM) and Salesforce Configure, Price, Quote (CPQ)/Revenue Cloud, including resolving complex quoting and cross-object issues.
• Strong understanding of commercial deal structures, including annual recurring revenue (ARR), multi-year agreements, amendments, renewals, co-terms, ramps, stub billing, bundled products, and discounting.
• Demonstrated ability to build or improve processes, documentation, approval workflows, and commercial policies in an evolving environment.
• Sound commercial judgment—balancing customer and seller needs with pricing discipline, revenue integrity, and business risk.
• Strong cross-functional communication skills, including the ability to influence without formal authority and explain complex commercial concepts clearly.

Preferred Qualifications

• Experience using artificial intelligence (AI), automation, or workflow tools to reduce manual work and improve the quote-to-cash process.

Compensation & Benefits

USA-based roles only

• Annual base salary: between $96,000 USD and $134,000 USD.
• Eligible for immediate participation in the benefits program (health, dental, 401k and many others), generous paid time off, an equity grant, and, where applicable, participation in incentive programs.

Canada-based roles only

• Annual base salary: between $89,000 CAD and $125,000 CAD.
• Eligible for immediate participation in the benefits program (health, dental, RRSP and many others), generous paid time off, an equity grant, and, where applicable, participation in incentive programs.

Compensation is approached with a promise of fair market value and internal equity commensurate with experience and specific skill set.

Location

• Remote role based in North America, supporting teams across the United States and Canada.
• This is a remote opportunity within Canada and the US.
• Note: All go-to market roles will have an in-person onboarding in Toronto.

Additional Information

• Occasional travel may be required, including department-wide offsites, quarterly department meetings, and periodic customer events held in varying locations across Canada, USA and/or EMEA.
• In leadership roles, travel is expected once per month on average.
• This posting is for an existing vacancy.
• Accommodation is available upon request during the recruitment process.
• Successful applicants will be required to complete a background check as permitted by local law.
• Remote work is part of the organization’s operating model and is performed from the home country.