Senior Deal Desk Analyst

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Deal Desk Analyst based in Canada.

This role offers the opportunity to become a key driver of efficient revenue operations within a fast-growing SaaS environment. You will own the end-to-end deal lifecycle, ensuring sales teams can close opportunities smoothly while maintaining strong financial accuracy. The position combines strategic process improvement, operational execution, and cross-functional collaboration across Sales, Finance, Customer Success, and Legal teams. You will help build scalable systems that simplify quoting, invoicing, renewals, and customer billing workflows. The ideal candidate will bring strong analytical skills, SaaS billing expertise, and the ability to solve complex deal challenges. You will play an important role in removing operational friction, improving internal processes, and enabling teams to deliver a better customer experience.

Accountabilities:: As a Senior Deal Desk Analyst, you will take ownership of deal operations from initial review through final processing, ensuring commercial agreements are structured effectively and executed accurately. You will partner with multiple teams to streamline workflows, manage complex transactions, and create scalable processes that support business growth.

Own the complete deal lifecycle by reviewing and approving standard order forms, discounts, and payment terms to support efficient sales execution.

Manage complex new business opportunities and renewals, including multi-year agreements, custom payment structures, and non-standard commercial terms.

Collaborate with sales teams before quotes are submitted to ensure deals are structured for accurate booking and invoicing.

Act as the main point of contact for external commercial counsel regarding customer contract reviews, redlines, and legal communications.

Improve and scale routine deal processes by redesigning manual order form and invoicing workflows into efficient, repeatable systems.

Build and maintain operational controls, templates, approval processes, and CRM/CPQ configurations to support accurate deal execution.

Identify process bottlenecks across systems and workflows, including CRM, payment platforms, and internal operations, and implement improvements.

Partner with Customer Success teams to enable independent handling of common billing updates, refunds, and payment-related actions.

Create documentation, playbooks, and guidelines that define when teams can act independently and when escalation is required.

Ensure financial accuracy by maintaining correct billing terms, clean payment records, accurate CRM information, and reliable revenue data.

Support Accounting teams during month-end close by resolving non-standard transactions and ensuring clean financial records.

Requirements:

The ideal candidate is an experienced revenue operations professional with strong knowledge of deal management, SaaS billing processes, and cross-functional business operations. You should be comfortable working with sales, finance, and customer teams while improving systems and creating scalable processes.

3–7 years of experience in deal desk, revenue operations, billing operations, or a similar role managing end-to-end quote-to-cash processes.

Strong working knowledge of Stripe, including invoicing, subscriptions, refunds, and dispute management.

Hands-on experience with CPQ tools and CRM platforms such as HubSpot or Salesforce, including configuring rules and approval workflows.

Strong analytical and spreadsheet skills with the ability to model deal structures, evaluate terms, and identify inconsistencies.

Experience with SaaS subscription billing, particularly in environments involving multi-year contracts or complex customer segments.

Understanding of accounting processes and how accurate upstream data impacts financial reporting.

Experience training and enabling non-finance teams such as Account Executives and Customer Success Managers.

Ability to use AI tools to improve operational efficiency and automate routine tasks.

Strong communication, problem-solving, organizational, and stakeholder management skills.

Ability to manage multiple priorities while maintaining attention to detail in a fast-paced environment.

Benefits:

Competitive compensation package with Canadian salary details shared during the recruitment process.

Opportunity to work within a rapidly growing SaaS environment with meaningful impact.

Flexible work environment designed to support remote collaboration.

Comprehensive health, dental, and vision coverage for employees, with dependent coverage support.

Generous paid time off, including parental leave.

Retirement savings program.

Company-provided laptop and home-office support.

Company retreats held twice per year.

Opportunities for professional growth, ownership, and career development.

How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best!  Why Apply Through Jobgether?    Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.     #LI-CL1