Sr. Deal Desk Analyst

For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world’s most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.

At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.

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. The team values over-communication, intellectual curiosity, and a willingness to context-switch quickly across priorities.

You will report to the Director of FP&A and work closely with RevOps, Sales, Systems Design, and GTM leadership as a collaborative partner and reliable operational resource across the commercial side of the business.

This role sits at the center of deal desk operations and commercial finance, giving you a front-row seat to how deals get structured, priced, and closed. You will be deeply embedded in the quote-to-cash workflow from day one, owning deal reviews, pricing analysis, and the operational rigor that keeps the commercial motion running cleanly.

You are the kind of person who thrives on precision and process. You catch what others miss, you follow through without cutting corners, and you are comfortable owning the final review on deals before they close. You bring a natural attention to detail and a strong bias toward execution.

Gladly’s commercial motion is accelerating, and the Finance team is scaling to match. You will play a central role in that, helping build the operational rigor that supports a growing deal volume while also supporting pricing analysis and margin modeling that inform deal structure decisions.

Deal Desk & Commercial Finance Operations

• Conduct deal reviews for completeness, accuracy, and compliance before close, ensuring all required approvals are in place and deals are structured correctly across pricing, discounting, and contract terms
• Review deals for compliance with pricing guidelines, discount thresholds, and revenue recognition requirements (ASC 606); escalate edge cases to Finance leadership as needed
• 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
• Support and over time own the margin calculator used to evaluate different pricing structures when working with the sales team on custom-priced enterprise deals, including analysis of AI vs. Team margin dynamics
• Partner with Sales Operations and Systems Design on Deal Desk process alignment, consulting on workflow design and driving consistent execution once processes are defined and deployed
• Bring a continuous improvement mindset: flag friction points in the Deal Desk process and collaborate with SalesOps and Systems Design on solutions, with a longer-term eye toward automating manual steps

Systems Administration & Process Design

• Support deal desk systems including DealHub (CPQ), Salesforce, and related commercial tools, ensuring data integrity and process consistency
• Partner with the Systems Design team on configuring and optimizing deal desk tooling, including approval workflows, pricing rules, and quote templates
• Help identify opportunities to automate recurring processes and reduce manual effort across the deal desk function over time

AI and Automation

• Show genuine curiosity about AI tools (Claude, ChatGPT, Copilot, or similar) and a willingness to learn how they can help you move faster and reduce the lift on repetitive tasks
• Apply an automation-first lens to your own work: if you are doing something manually more than twice, start thinking about how to streamline it
• Partner with the Finance team on identifying and implementing AI-assisted workflows across Deal Desk processes

• 3-5 years of experience in deal desk, commercial finance, or a related operational finance role. B2B SaaS experience is a strong plus but not required
• English proficiency at C1-C2 level (business fluent). This role requires daily written and verbal communication with US-based teams
• Based in Colombia or Mexico with the ability to work US business hours
• Deal desk or quote-to-cash experience: you understand deal review, pricing compliance, approval workflows, and what it takes to close a deal cleanly
• Salesforce proficiency: comfortable navigating opportunity records, pipeline reports, and deal data independently. You work in the system, not just look at it
• Solid grasp of SaaS business model fundamentals: ARR, ACV, NRR, and SaaS revenue recognition (ASC 606)
• Comfortable with pricing analysis and margin modeling: you can work within existing models and help evaluate the financial impact of different deal structures
• Advanced Google Sheets or Excel skills: complex formulas, pivot tables, scenario modeling, and data visualization
• High attention to detail and a strong sense of accountability. You follow through, you notice when something is off, and you say something
• Collaborative by nature: you partner well with Sales, RevOps, and Finance teammates and bring people along rather than going it alone
• DealHub, CPQ, or deal desk systems admin experience is a strong plus

Salary for this role: $60,000 - $90,000 USD annually DOE (may be paid in COL pesos depending on EOR/COR contract selection)

The cash compensation above includes base salary, and is not reflective of potential commission for employees in eligible roles, or annual bonus targets under Gladly's bonus plan for eligible roles. In addition to cash compensation, all Gladly employees are eligible to participate in Gladly's equity incentive plan to receive stock options per the terms of the agreement. Individual compensation packages are based on a few different factors unique to each candidate, including their career level, skills, experience, specific geographic location qualifications and other job-related reasons.