Head of Deal Strategy

Join Applecart as the Head of Deal Strategy in our New York City office. In this high-impact role, you will be responsible for architecting our commercial engagements, structuring complex deals, and developing compelling pricing strategies. You will work closely with various internal teams and report to the SVP of Revenue Operations. This position offers a competitive salary, extensive benefits, and a hybrid work setup.

• Lead the commercial architecture for Applecart, serving as the strategic partner and final sign-off for all proposals.
• Partner with the Business Development team to architect highly complex deals, translating novel product capabilities into compelling value narratives.
• Create the strategic frameworks that allow the sales team to move fast and remain creative without breaking unit economics.
• Enterprise-Level Commercial Track Record: Proven experience structuring and positioning highly complex, bespoke Enterprise deals requiring thoughtful, C-suite-level presentation and strategic price selection
• Novel Pricing Familiarity: Experience dealing with complex or novel monetization models, particularly usage-based or consumption models (e.g., explaining the strategic value of tokens, credits, or data tiers to executive buyers)
• Strategic Intuition & Visual Communication: The ability to look at a raw deal and instantly identify the 2–3 levers that will make it compelling for a client. Proficiency in designing proposals and presentations that make it easy for an enterprise buyer to say "yes."
• Versatility Across Industries: A proven track record of success across multiple industries or distinct product verticals, demonstrating the agility to quickly learn a new space, understand varying buyer psychologies, and adapt commercial strategies
• Enterprise Deal Strategy Background: 6+ years of experience leading Deal Strategy, Deal Desk, or Revenue Operations in a software, SaaS, or high-touch consulting environment
• Thriving in Ambiguity: A strong desire and demonstrated ability to operate successfully in a high-growth, fast-paced, and fluid entrepreneurial environment. You are comfortable building the framework while executing the strategy
• High Executive Presence & Drive: Exceptional communication skills and the professional gravity required to interact effectively, challenge, and collaborate with seasoned, 20+ year BD veterans and executive leadership