Deal Desk Director Jobs (NOW HIRING)

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 alongside experienced deal desk and systems teammates. You will have direct exposure to how deals move through the commercial pipeline and how the systems that support that process are built and maintained.

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.

You are detail-oriented, execution-focused, and energized by operational work that has real business impact. You do not wait to be told what to do next. You see a gap, you close it. You are not intimidated by ambiguity or new systems, and you bring the kind of follow-through and accountability that earns trust fast. You may be earlier in your career, but you operate like someone who has been doing this for years.

Gladly is at the forefront of AI-powered customer experience, and our commercial motion is accelerating to match. This role gives you direct responsibility across deal review, pricing analysis, systems configuration, and cross-functional partnership with sales. The technology is evolving fast, the deal structures are evolving with it, and the right person in this seat will grow into a core operator on the Finance team, not stay in a support role.

• 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

• 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
• Assist with 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

• 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

• 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

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.

• Competitive salaries, stock options, and comprehensive benefits
• Generous paid time off, parental leave, and home office stipends
• A fully remote work environment with opportunities for in-person team gatherings
• A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive
• A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily

We’re a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics.

If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.