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Role Description
As the Deal Desk Manager, you will lead and develop a high-performing team responsible for deal review, recommendations, execution, and operational scaling within our Global Sales and Channel organization. You will be a trusted advisor to sales and cross-functional leadership, shaping objectives, monitoring team effectiveness, and ensuring alignment of tactical activities with strategic business outcomes. Your role is pivotal in fostering strong stakeholder relationships with sales managers and leaders, maintaining a customer-centric approach, and driving continuous improvements in deal velocity and compliance.
You will oversee complex proposal evaluation and process, licensing model analysis, and contract structuring while innovating scalable processes that enhance efficiency and deal closure rates. This role demands a strategic mindset, exceptional communication skills, and the ability to navigate ambiguity in a fast-evolving SaaS sales environment.
Responsibilities- Define and execute the operational strategy for the Deal Desk team aligned with broader sales objectives.
- Lead, mentor, and manage a team of Deal Desk Analysts, setting clear performance targets and regularly communicating progress to stakeholders.
- Serve as the primary liaison between sales, legal, and finance teams to craft and consult on complex deal proposals.
- Analyze licensing models and recommend optimal contract structures to maximize revenue and customer satisfaction.
- Act as the escalation point for complex deal issues, providing expert guidance on alternative contract options and value propositioning.
- Develop and implement initiatives to improve Deal Desk productivity, simplify processes, and enhance compliance with revenue recognition policies.
- Minimum 2+ years managing a Deal Desk or similar function within an Enterprise SaaS or B2B sales environment.
- Minimum 2+ years of people management experience.
- At least 6 years of experience in deal desk strategy, sales operations, or related roles involving complex pricing and proposal execution.
- Proven ability to lead cross-functional teams and manage stakeholder relationships effectively.
- Expertise in licensing models, contract structuring, and compliance with revenue recognition standards.
- Strong proficiency with Salesforce, CPQ tools, and reporting/analytics platforms.
- Exceptional communication skills, both verbal and written, with a customer-centric and transparent style.
- Ability to multitask and prioritize effectively during high-volume periods, including quarter-end and year-end cycles.
- Experience scaling Deal Desk operations in a high-growth SaaS environment.
- Advanced skills in Salesforce report building and data-driven decision making.
- Familiarity with sales enablement tools and process automation.
- Prior experience delivering training and developing talent within sales operations teams.
US Zone 1
This role is not available in Zone 1
US Zone 2
$139,700—$188,900 USD
US Zone 3
$124,100—$167,900 USD
Dropbox Chicago, Illinois, USA Office
Chicago, IL, United States
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
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- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
