Senior Deal Desk Lead

Role Overview

Halcyon is looking for a highly experienced Senior Deal Desk Lead to build and operate a disciplined, scalable approach to commercial deal evaluation and approval. The Senior Deal Desk Lead will serve as a strategic partner to Sales and cross-functional stakeholders, helping ensure deals are structured thoughtfully, evaluated consistently, and routed through the appropriate approval levels based on established criteria.

What You Will Do

The Senior Deal Desk Lead will analyze complex and non-standard transactions across pricing, discounting, contract structure, payment terms, product and service considerations, renewal implications, and other commercial elements. They will provide clear recommendations, identify potential risks and trade-offs, and ensure decision-makers have the context necessary to make informed approvals.

Why It Might Be a Fit

The ideal candidate combines strong commercial judgment, analytical rigor, operational discipline, and the ability to influence and educate teams across the organization. They should be able to balance speed and flexibility with the need to protect long-term customer and company value.

Requirements

• 7+ years of experience in Deal Desk, Revenue Operations, Sales Operations, Commercial Operations, Finance, or a similar role within a high-growth SaaS or technology company
• Strong understanding of SaaS and enterprise software deal structures, including pricing, discounting, contract terms, payment structures, renewals, and commercial concessions
• Demonstrated experience evaluating complex transactions and providing recommendations to sales and executive stakeholders
• Strong financial and analytical skills with the ability to assess the complete economics of a deal and understand the implications of different commercial structures
• Experience working within structured approval frameworks and applying defined levels of authority to commercial decisions
• Strong commercial judgment with the ability to balance customer requirements, revenue objectives, risk, and long-term company value
• Ability to identify and clearly articulate financial, operational, contractual, and precedent implications associated with deal decisions
• Demonstrated ability to educate and influence teams, helping stakeholders understand both commercial guardrails and the rationale behind them
• Strong problem-solving skills with the ability to develop alternative deal structures when an initial proposal does not meet established criteria
• Excellent written and verbal communication skills, including the ability to present complex deal considerations clearly and concisely to senior decision-makers
• Strong cross-functional collaboration skills with experience partnering across Sales, Finance, Legal, Revenue Operations, Customer Success, and executive leadership
• High attention to detail and a consistent, disciplined approach to commercial decision-making
• Ability to operate effectively in a fast-paced environment while managing multiple time-sensitive transactions and competing priorities
• Experience with CRM, CPQ, contract lifecycle management, and related revenue technology platforms preferred

Benefits

• Comprehensive healthcare (medical, dental, and vision) with premiums paid in full for employees and dependents
• Short and long-term disability coverage, basic life and AD&D insurance plans
• Medical and dependent care FSA options
• 401k plan with a generous employer contribution
• Flexible PTO policy
• Parental leave
• Generous equity offerings

Tagged as: Deal Desk