Director, Deal Desk & Strategy

Fastly•San Francisco, CA

2d•Hybrid

About The Position

Fastly is seeking a Director, Deal Desk to lead and scale our global deal strategy function within a high-growth technology environment. In this role, you will act as a trusted advisor to Sales teams across North America, EMEA, and APAC, guiding complex deal structures. You will collaborate with cross-functional teams to optimize pricing, discounting, and contract terms to accelerate deal velocity and maximize revenue and profitability. Partnering cross-functionally with Finance, Sales Operations, Legal, and Systems, you will ensure deals are structured, approved, and executed with accuracy and efficiency. Success will be measured by your ability to enable scalable deal formation, improve sales productivity, and deliver data-driven insights that support sustainable growth.

Requirements

Bachelor’s degree in Business, Finance, Accounting, or a related field.
12+ years of progressive experience in Deal Desk, Sales Operations, Finance, or related functions, with deep expertise in usage-based business models.
6+ years of people leadership experience, with a proven ability to build and scale high-performing teams; strong background in deal structuring and managing high contract volume.
Demonstrated success leading and scaling a Deal Desk, including process optimization and transformation.
Strong understanding of revenue recognition (GAAP), compliance (including SOX), and financial, legal, and operational risk considerations.
Experience with CRM and CPQ tools and billing systems, with the ability to translate business needs into scalable system solutions.
Excellent analytical, problem-solving, and negotiation skills, with a track record of structuring complex deals and driving revenue growth and profitability.
Executive-level communication skills, with the ability to influence and collaborate effectively across all levels of the organization.

Nice To Haves

Experience in edge computing, cloud, security, or other high-growth infrastructure technology sectors
Exposure to AI/ML-driven products, pricing models, or a strong curiosity and willingness to learn emerging technologies
Advanced financial modeling skills, including scenario analysis for complex, non-standard deal structures
Track record of leveraging data, analytics, and automation to inform deal strategy and improve decision-making

Responsibilities

Lead and scale global Deal Desk, leveraging automation and standardization to improve deal velocity and accuracy.
Build, develop, and mentor a high-performing Deal Desk team, fostering a culture of accountability, collaboration, and continuous improvement.
Develop and execute deal strategies, pricing frameworks, and approval processes that drive revenue growth and maximize profitability.
Partner cross-functionally with Sales, Finance, Legal, Accounting, Product, and Business Units to structure complex deals, ensuring alignment with financial, legal, and operational requirements.
Drive process optimization and systems enhancements (e.g., CPQ), translating business requirements into scalable solutions that improve the seller and customer experience.
Establish and enforce deal governance, including risk assessment, policy development, performance tracking, and data-driven insights to inform strategic decision-making.