Deal Desk Manager

About the role

You will own the end to end management of complex sales deals from initial quote generation through final booking, ensuring that every transaction aligns with our strategic revenue goals. In this role, you act as the central point of operational excellence within the Revenue Operations team, removing friction and roadblocks that slow down the sales cycle. You will partner directly with the Senior Deal Desk Manager to provide full team coverage and eliminate single points of failure, ensuring continuity and resilience. By becoming a master of our CPQ tools and Salesforce configuration, you will identify process gaps and drive enhancements that increase accuracy and speed. You will design and deploy automation and self service solutions that reduce manual intervention, allowing sales representatives to own routine deals independently. You will own the creation and maintenance of deal desk playbooks, approval protocols, and documentation to enforce consistency and reduce redundant reviews. You will analyze performance metrics to inform pricing policies and deal structures, translating raw data into actionable strategic insights. You will collaborate cross functionally to maintain alignment on deal structures, fostering a unified approach to revenue generation that supports the developer mission of the company.

Key facts

What you'll do

• Oversee the complete deal lifecycle, which encompasses generating quotes, evaluating discounts, producing order forms, and facilitating approvals with efficiency and minimal escalation.
• Work closely with the Senior Deal Desk Manager to guarantee that all deals are comprehensively covered, thereby avoiding any potential single points of failure within the team.
• Become an expert in our Configure Price Quote (CPQ) system and its integration with Salesforce, pinpointing areas for enhancement, documenting issues, and collaborating with the Go-To-Market Technology team to implement necessary changes.
• Create and deploy automated solutions and self service options to decrease the necessity for manual Deal Desk involvement, enabling sales representatives to manage routine deals autonomously.
• Develop and sustain deal desk playbooks, approval protocols, and process documentation to ensure uniformity and reduce the frequency of repetitive reviews.
• Assist in updating pricing by accurately and swiftly reflecting changes in the CPQ system, while proactively identifying potential downstream effects for the sales team.
• Analyze deal related data, including approval rates, types of exceptions, and deal velocity, to provide insights that guide policy and pricing strategies.
• Collaborate with cross functional teams to ensure alignment on deal structures and pricing strategies, fostering a cohesive approach to revenue generation.
• Utilize AI tools such as Copilot, ChatGPT, or specialized Revenue Operations tools to expedite deal reviews, summarization, or exception routing.
• Maintain strict governance over discounting and contract terms to protect margin while enabling competitive positioning in the market.
• Serve as the primary escalation handler for complex deals, balancing speed of execution with adherence to policy and compliance standards.
• Partner with Finance to reconcile booked revenue, ensuring accuracy between the CRM, billing systems, and financial reports.
• Proactively monitor the health of the sales pipeline, identifying bottlenecks and coaching sales teams on best practices for deal progression.
• Implement quality assurance processes for deal documentation, ensuring that all order forms and approvals meet internal audit requirements.
• Facilitate regular reviews of deal desk performance metrics, driving continuous improvement initiatives across the revenue operations function.
• Act as a subject matter expert for the sales organization, providing training and guidance on CPQ configurations and pricing rules.
• Coordinate with Legal and Customer Success to ensure that contractual language supports long term customer relationships and reduces friction.
• Drive adoption of new tools and processes by creating enablement materials and conducting hands on sessions for revenue teams.

Requirements

• A minimum of 5 years of experience in Deal Desk, Sales Operations, Revenue Operations, or a related role within a B2B SaaS environment.
• Hands on experience with CPQ tools such as Dealhub, Salesforce CPQ, or MonetizeNow, with a solid understanding of quoting logic, product catalogs, and approval workflows.
• Proficiency in Salesforce, with a strong grasp of objects, fields, and reporting capabilities, enabling effective communication with Salesforce administrators regarding necessary modifications.
• Experience managing the entire deal lifecycle, including quoting, redlining, order forms, and booking processes.
• Strong analytical capabilities, with the ability to build models or reports that address specific inquiries and identify relevant questions.
• A demonstrated track record of enhancing existing processes rather than merely executing them as they are.
• Familiarity with AI tools such as Copilot, ChatGPT, or specialized Revenue Operations tools to expedite deal reviews, summarization, or exception routing.
• A commitment to maintaining data integrity and ensuring that all deal information is accurate, auditable, and timely.
• The ability to work independently and collaboratively in a fast paced, dynamic startup environment while managing multiple priorities.

Nice to have

• Knowledge of various SaaS pricing models, including usage based, ramped, or multi product pricing structures.
• Experience in supporting both new business and renewal processes, with an understanding of the significance of clear role delineation within these processes.
• Exposure to contract negotiation and legal review processes, providing a well rounded perspective on deal management.

Practical notes

This position operates in a hybrid work environment. Sentry is committed to being an equal opportunity employer and offers reasonable accommodations for individuals with disabilities. For assistance, please reach out to accommodations@sentry.io. We encourage applications from diverse backgrounds and experiences, as we believe that a variety of perspectives strengthens our team and enhances our ability to serve our clients effectively. If you are about improving sales processes and have the requisite experience, we would love to hear from you. Join us in our mission to empower developers and enhance software performance!