Role Overview:

We are seeking an accomplished Director of DealDesk Operations to lead and scale our deal structuring, pricing strategy, and contract execution processes. This pivotal role will serve as a strategic partner to Sales, Customer Success, and Finance leadership, shaping commercial best practices and driving profitable revenue growth. The Director will be responsible for building a high-performing DealDesk function, optimizing the quote-to-cash process, and serving as the primary escalation point for complex, high-value customer engagements.

Key Responsibilities:

Strategic Leadership & Stakeholder Management:

• Lead, mentor, and develop a team of DealDesk professionals, fostering a culture of operational excellence and continuous improvement.
• Collaborate closely with Sales, Finance, and Legal to define and enforce deal policies, pricing guidelines, and approval matrices.
• Act as the primary escalation point for non-standard deals, ensuring alignment with corporate strategy and financial objectives.
• Provide strategic guidance to Customer Success and Account Management teams on renewal pricing, upsell, and cross-sell opportunities; partner with Renewal AEs on key customer negotiations.
• Partner with senior leadership to inform go-to-market strategies, product bundling initiatives, and commercial terms optimization.

Deal & Pricing Operations:

• Oversee the end-to-end deal process, from approved quote through contract execution, ensuring speed, accuracy, and compliance.
• Engage directly with internal stakeholders and customers to clarify pricing, terms, and approval processes for complex transactions.
• Own pricing and discount analysis, delivering actionable insights to improve deal profitability and maintain pricing discipline.

Operational Excellence & Systems:

• Drive the implementation, adoption, and optimization of CPQ and related sales systems to streamline the quote-to-cash process.
• Identify process inefficiencies and implement scalable improvements across the sales cycle.
• Design and deliver training for Sales and CS teams on deal desk policies, processes, and best practices.

Data, Analytics & Reporting:

• Define and monitor KPIs for DealDesk performance, including:
  • Average deal cycle time
  • Discount levels and margin impact
  • Renewal rates and upsell revenue
  • Forecasting accuracy

• Build and maintain dashboards providing real-time insights for executive leadership.
• Present regular performance updates and recommendations to senior leadership.