Deal Desk Lead

Prolific•San Francisco, CA

5h•Remote

About The Position

Prolific is seeking a Deal Desk & Solutions leader to architect and operationalize how complex AI data, evaluation, and managed service deals are scoped, priced, and closed. This role sits at the intersection of Sales, Product, Customer Success, and Operations, ensuring that enterprise and strategic deals are commercially viable, operationally deliverable, and strategically aligned with Prolific’s evolving platform and services model. Prolific is not just another player in the AI space – they are the architects of the human data infrastructure that's reshaping the landscape of AI development. In a world where foundational AI technologies are increasingly commoditized, it's the quality and diversity of human-generated data that truly differentiates products and models.

Requirements

7+ years in Deal Desk, Commercial Strategy, RevOps, Solutions, or similar in a SaaS, data, or AI environment
Experience structuring complex enterprise deals (usage-based, services, or hybrid models)
Strong grounding in pricing, cost modeling, and margin management
Ability to translate ambiguous customer needs into clear, executable scopes of work
Experience working cross-functionally across Sales, Product, and Delivery/Operations
Proven ability to build or improve deal processes, pricing frameworks, or approval workflows
Strong commercial judgment with a track record of identifying risk and improving deal quality
Excellent stakeholder management and ability to influence senior leaders

Nice To Haves

Experience in AI/ML, data services, or human-in-the-loop workflows
Familiarity with usage-based or platform + services pricing models

Responsibilities

Partnering with Account Executives and Solutions Consultants to shape deal pricing and delivery structures for strategic and enterprise opportunities.
Translating customer needs into clear, executable commercial proposals, including scope of work, delivery assumptions, and packaging (usage, subscription, and managed services).
Introducing practical guardrails to improve deal velocity, win rate, and margin consistency.
Leading cross-functional scoping with Operations and Quality/Research/Evaluation to ensure proposed solutions are deliverable and scalable.
Validating delivery approach against Prolific’s workforce model (crowd, expert, hybrid), including realistic SLAs, QA standards, and resourcing assumptions.
Building repeatable ways of scoping AI data and evaluation programs to reduce ambiguity and execution risk.
Owning and iterating pricing frameworks, cost models, and rate cards across platform usage, managed services, and expert-led work.
Driving consistency in deal economics by defining margin expectations, escalation paths, and approval thresholds.
Acting as the connective tissue across Sales, Revenue Leadership, Operations/Delivery, and Quality to align on scope, resourcing, and timeline assumptions.
Improving pre-sales → delivery handoffs through clear documentation, ownership, and readiness criteria.
Building and scaling a formal Deal Desk function, including scoping templates, pricing calculators and approval frameworks
Supporting deal review processes led by Revenue Leadership
Creating repeatable workflows that reduce friction and ambiguity
Advising Account Executives and Revenue Leadership on complex, high-value opportunities.
Providing structuring recommendations, pricing guidance, and early risk identification (delivery, margin, and quality).
Joining key deal cycles as a commercial and operational partner when needed.