Senior Deal Desk Lead

The Role: 

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. 

This role is not simply focused on processing approvals. The Senior Deal Desk Lead will help educate teams on how to construct strong deals, understand the commercial implications of proposed terms, and navigate established deal parameters with greater confidence and consistency. 

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. 

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. 

Responsibilities:  

• Serve as the primary point of coordination for the evaluation of complex and non-standard commercial deals.  
• Analyze proposed deal structures against established commercial criteria, policies, and approval levels.  
• Provide clear, data-informed recommendations on deal exceptions, including the financial, commercial, operational, and long-term implications of proposed terms.  
• Ensure deals requiring exceptions are routed to the appropriate decision-makers based on established levels of authority.  
• Partner closely with Sales to help structure deals that address customer requirements while supporting Halcyon’s commercial objectives.  
• Educate sellers, managers, and other stakeholders on deal criteria, approval requirements, pricing principles, and commercial best practices.  
• Help teams understand the rationale behind commercial policies and approval decisions so that deal quality improves at the point of creation.  
• Evaluate the complete economics and structure of a transaction, including pricing, discounting, contract duration, payment terms, product mix, services, concessions, renewal considerations, and other relevant factors.  
• Identify financial, operational, contractual, and precedent risks associated with proposed deal structures.  
• Partner with Finance, Legal, Revenue Operations, Customer Success, Sales leadership, and other stakeholders to ensure proposed deals are aligned and executable.  
• Provide approvers with concise, objective analysis of exceptions, including the business rationale, risks, trade-offs, alternatives, and recommended path forward.  
• Apply established deal criteria consistently while exercising sound business judgment when circumstances require additional consideration.  
• Maintain clear documentation of deal reviews, recommendations, approvals, and exceptions.  
• Identify recurring deal patterns and exception trends that may indicate opportunities to improve commercial policies, pricing, packaging, processes, or field enablement.  
• Use insights from deal activity to improve the quality and consistency of commercial decision-making across the organization.  
• Help simplify and improve the deal review experience by identifying opportunities to reduce unnecessary friction and increase speed for deals that fall within established parameters.  
• Partner with Revenue Operations and business systems teams to improve the tools, workflows, and data required to support efficient deal evaluation and approval. 
• Support the continued evolution of Halcyon’s commercial practices as the company, customer base, product portfolio, and go-to-market strategy scale.  

Skills and Qualifications: 

• 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: 

Halcyon offers the following benefits to eligible employees: 

• 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. 

The Company reserves the right to modify or change these benefits programs at any time, with or without notice. 

The expected base salary range for this position is $175,000 - $215,000. Compensation varies based on a variety of factors which include (but are not limited to) role level, skills and competencies, qualifications, knowledge, location, and experience. In addition to base pay, certain roles are eligible to participate in our bonus or commission plans, as well as our benefits offers, and equity awards.