Contentsquare

Senior Deal Desk Strategist

Job Description

The Revenue Operations Department is seeking a Senior Deal Desk Strategist, a hands-on person who will collaborate closely with sales leadership, finance, and legal teams to ensure the smooth execution of complex deals, balancing both profitability and customer satisfaction.

In this role, you will partner with sales to manage complex Enterprise deal structuring, pricing strategies, and contract negotiations across the Americas. Your focus will be supporting and partnering to scale the deal desk function, partnering with internal teams to implement and optimize CPQ (Configure, Price, Quote) tools, and driving greater efficiency in the sales process.

This role requires a combination of strategic thinking, operational expertise, and hands-on experience with CPQ systems. You will serve as a trusted advisor to sales leadership, influencing key decision-making to drive revenue growth while maintaining profitability.



What you'll do:
  • Lead Deal Structuring: Oversee and manage the entire deal structuring and pricing process for high-value and complex SaaS contracts in partnership with sales, ensuring alignment with company goals and customer needs.
  • Pricing and Discount Management: Develop and refine pricing strategies, approval workflows, and discount frameworks to ensure deals meet financial and operational targets.
  • Cross-Functional Collaboration: Partner closely with Sales, Legal, Finance, Product, and Customer Success teams to ensure deal terms are consistent with corporate policies, legal requirements, and customer satisfaction goals.
  • Sales Enablement: Act as a trusted advisor to the sales team, providing guidance on deal strategies, pricing options, and non-standard contract terms to optimize win rates and margin preservation.
  • Process Optimization: Identify and implement process improvements to streamline deal approval workflows, reduce cycle times, and enhance the efficiency of the Deal Desk function.
  • Risk Management: Assess and mitigate risks associated with deal terms, including financial, legal, and operational risks, ensuring compliance with internal controls and external regulations.
  • Reporting and Analytics: Track and analyze deal performance metrics, providing actionable insights and recommendations to sales leadership and executive teams to drive continuous improvement.
  • Team Leadership: Mentor and help develop a high-performing Deal Desk team, fostering a culture of excellence, accountability, and collaboration.
  • CPQ System Management: Partner in overseeing the configuration and optimization of the CPQ system to ensure it aligns with business requirements. Collaborate with IT and business stakeholders to drive system enhancements and resolve issues.


    • What you'll need to succeed:
  • 6+ years in Enterprise deal desk, sales operations, or revenue operations roles. Prior experience managing a global team, B2B SaaS Experience and or Enterprise sales is highly preferred.
  • Proven experience with CPQ implementation, configuration, and optimization (preferably DealHub CPQ). Strong understanding of CPQ architecture and ability to customize and improve the system.
  • Bachelor's degree in Business, Finance, or a related field. MBA or equivalent is a plus.
  • Strong understanding of SaaS business models, including subscription-based pricing, renewals, upsells, and cross-sells.
  • Proficiency with Salesforce, CPQ systems, and contract management software. Advanced Excel and data analysis skills.
  • Exceptional verbal and written communication skills with the ability to present complex information to C-level executives.
  • Data-driven decision maker with strong problem-solving skills and the ability to translate insights into actionable strategies.

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