Deal Strategist

Jobtailor; San Francisco (CA); Hybrid; USD 180,000 - 240,000; Full time

Job summary

Jobtailor in San Francisco seeks an experienced Deal Strategy Leader to partner with Americas account teams on complex, high-value opportunities from initial strategy through proposal and closure.

You will craft ROI analyses, value narratives, and CFO-ready business cases, and you will apply AI to streamline deal briefs and knowledge retrieval, boosting speed and win rates.

Qualifications

• 8+ years of experience in deal strategy or related field.
• Experience partnering with sales on complex, high-value opportunities.
• Proven track record developing ROI models or business cases.
• Strong communication and storytelling skills.
• Ability to translate complex products into clear customer narratives.
• Experience collaborating across Sales, Finance, Product, Legal, Pricing, and Operations.
• Familiarity with AI to improve workflows.

Responsibilities

• Partner with AMER account teams on strategic, high-value deals from strategy through closure.
• Develop deal strategies balancing customer priorities, pricing, and business objectives.
• Create executive-ready proposals, ROI analyses, and business cases.
• Support executive conversations with recommended options and rationale.
• Build ROI frameworks, proposal templates, and value narratives.
• Contribute to negotiation playbooks and intake processes.
• Collaborate with Pricing, Finance, Product, Legal, and Revenue Operations.
• Translate insights from strategic deals into reusable resources.
• Apply AI to automate deal briefs and improve workflows.
• Share recurring themes to inform commercial approaches.

Skills

Deal Strategy Development

ROI Analysis Creation

Cross-Functional Collaboration

Complex Proposal Development

AI Workflow Improvement

Tools

Proposal Templates

ROI Frameworks

Negotiation Playbooks

Automated Deal Briefs

Knowledge Retrieval Systems

Job description

• Partner with AMER account teams on complex, high-value, and strategic opportunities from initial deal strategy through proposal, negotiation, and closure
• Develop deal strategies combining customer priorities, commercial considerations, competitive positioning, and OpenAI's business objectives
• Create executive- and CFO-ready proposals, ROI analyses, value narratives, and business cases for complex and first-of-kind deals
• Support customer and executive conversations by presenting recommendations, business cases, and commercial rationale
• Build and maintain ROI frameworks, calculators, proposal templates, and value narratives
• Contribute to negotiation playbooks, deal clinics, office hours, and structured intake processes
• Partner with Pricing, Deal Desk, Finance, Product, Legal, Revenue Operations, Enablement, and Strategy
• Turn lessons from strategic and bespoke deals into reusable resources that improve speed, consistency, and seller productivity
• Apply AI to improve deal workflows and scalability through automated deal briefs, knowledge retrieval, guided proposal development, and self-service resources
• Identify recurring themes across strategic deals and share insights informing commercial approaches, field motions, products, and policies
• Report to the Americas Deal Strategy Leader

Requirements

• 8+ years of experience in deal strategy, strategic sales, strategic pricing, commercial strategy, or a related function
• Experience partnering directly with sales teams on highly complex, high-value, or first-of-kind commercial opportunities
• Track record of personally developing deal strategies, customer proposals, ROI models, or business cases that helped advance commercial outcomes
• Strong communication and storytelling skills
• Ability to translate complex products and commercial concepts into clear, compelling customer narratives
• Financial and analytical rigor, including experience developing ROI analyses and executive- or CFO-ready materials
• Experience working across Sales, Finance, Product, Legal, Pricing, and Operations to navigate complex commercial decisions
• Strong judgment and ability to bring structure and clarity to ambiguous or highly bespoke commercial situations
• Collaborative, hands‑on approach and comfort working directly with account teams and customers in fast‑moving deal cycles
• Familiarity with using AI to improve workflows, scale expertise, and increase productivity
• Ability to work from a US office three days per week
• Work authorization in the country where the job is located

Core Competencies

Demonstrates expertise in developing deal strategies, customer proposals, and ROI analyses to drive complex commercial outcomes. Proficient in collaborating with cross‑functional teams and leveraging AI to enhance deal workflows and productivity.

Highest-signal resume keywords

• Deal Strategy Development
• ROI Analysis Creation
• Cross‑Functional Collaboration
• Complex Proposal Development
• AI Workflow Improvement

Hard Skills

• Deal Strategy
• Strategic Sales
• Commercial Strategy
• ROI Modeling
• Business Case Development
• Financial Analysis
• Negotiation Skills
• Proposal Writing
• Customer Narrative Development
• Analytical Rigor

Soft Skills

• Strong Communication
• Storytelling Skills
• Judgment
• Collaboration
• Adaptability

Industry Keywords

• High‑Value Opportunities
• Complex Commercial Decisions
• Sales Operations
• Pricing Strategy
• Executive Presentations

Tools & Technologies

• Proposal Templates
• ROI Frameworks
• Negotiation Playbooks
• Automated Deal Briefs
• Knowledge Retrieval Systems