Deal Desk Analyst

About the role

The Finance team at Gladly is small, high-performing, and operates well above its weight class. The culture here is defined by high autonomy, direct visibility with leadership, and a bias toward action over process. Your work directly impacts how deals close and how leadership makes decisions. There are no layers, no committees, and no waiting around for approval.

Opportunity

This role puts you at the center of deal desk operations and commercial finance at a company redefining customer experience through agentic AI. You will start by working alongside experienced Finance and Systems teammates to build fluency in how deals get structured, priced, and closed, and you will move quickly toward ownership of the quote-to-cash workflow. This is not a back-seat role. We are looking for someone who learns fast, takes initiative, and is ready to own outcomes within their first six months.

What You'll Do

• Deal Desk Operations Support deal reviews for completeness, accuracy, and compliance before close, working alongside senior Finance teammates to ensure deals are structured correctly across pricing, discounting, and contract terms
• Help manage the day-to-day quote-to-cash workflow in Salesforce: deal progression tracking, certification process management, renewals tracking, and pipeline reporting
• Maintain a clean approval audit trail and deal log to support accurate pipeline reporting and downstream revenue recognition
• Learn and apply pricing compliance guidelines, discount thresholds, and revenue recognition requirements (ASC 606) with increasing independence over time
• Support the margin calculator used to evaluate pricing structures on enterprise deals, building comfort with how AI vs. Team margin dynamics affect deal economics
• Flag friction points in the Deal Desk process and bring ideas for improvement to the team
• Systems Support & Process Design Help support deal desk systems including DealHub (CPQ) and Salesforce, contributing to data integrity and process consistency under the guidance of the Systems Design team
• Aid in configuring and optimizing deal desk tooling, including approval workflows, pricing rules, and quote templates
• Identify opportunities to automate recurring processes and reduce manual effort across the deal desk function
• Partner with the Finance team on identifying and implementing AI-assisted workflows across Deal Desk processes

What We're Looking For

• 2-4 years of experience in deal desk, commercial finance, revenue operations, sales operations, or a related operational finance role. B2B SaaS experience is a plus but not required
• Based in the US with the ability to work standard US business hours
• Exposure to deal desk or quote-to-cash processes: you have some familiarity with deal review, pricing compliance, approval workflows, or commercial operations even if you have not owned the full function
• Salesforce experience: comfortable navigating the platform and working with deal data. Admin-level experience is a plus
• Familiarity with SaaS business model fundamentals: ARR, ACV, and how subscription revenue works. You do not need to be an expert, but you should understand the basics
• Comfortable with spreadsheets: Google Sheets or Excel at an intermediate-to-advanced level (formulas, pivot tables, data analysis)
• Strong attention to detail and follow-through. You notice when something is off and you do not let it slide
• A bias toward action and execution. You do not need to be told what to do next, you figure it out
• Collaborative and communicative: you over-communicate, you ask good questions, and you are comfortable working across teams
• DealHub, CPQ, or deal desk systems experience is a strong differentiator

Compensation

The expected OTE for this role is $85,000-$100,000, inclusive of base salary plus equity. Final offer amounts are determined by multiple factors including candidate experience, expertise, and geographic location. For cash compensation, we set standard ranges based on function, level, and geographic location, benchmarked against similar-stage growth companies. Research has shown that individuals from underrepresented groups are less likely to apply to jobs where they don't meet 100% of the criteria. Gladly values diversity of experience. If you believe you have the right skill set, we welcome you to apply even if you don't check every box. We are committed to an inclusive workplace and would love to see if you could be the next great addition to our team.