Head of Deal Strategy

Applecart•New York, NY

1d•$180,000 - $200,000•Hybrid

About The Position

As the Head of Deal Strategy at Applecart, you will be the architect of our commercial engagements. You will work alongside senior members of our Business Development team who typically have 20+ years of experience at leading firms in public affairs, communications, and enterprise sales to win new clients and expand existing accounts. Our pricing is a strategic lever, not a static list. We are looking for a commercial strategist to take the mental model of our leadership team and turn it into a scalable, high-conversion engine. You will be the final authority on how we structure, story-tell, and close complex deals, ensuring every proposal that leaves the building is optimized to deliver maximum customer value while maintaining internal margin control. You will work closely with Sales, Business Development, Operations, Legal, Finance, and Executive Leadership to develop compelling pricing strategies and proposals for Applecart’s clients. Reporting to the SVP, Revenue Operations, this will be a high impact role, helping drive profitable revenue growth.

Requirements

6+ years of experience leading Deal Strategy, Deal Desk, or Revenue Operations in a software, SaaS, or high-touch consulting environment.
Proven experience structuring and positioning highly complex, bespoke Enterprise deals requiring thoughtful, C-suite-level presentation and strategic price selection.
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.
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).
Exceptional communication skills and the professional gravity required to interact effectively, challenge, and collaborate with seasoned, 20+ year BD veterans and executive leadership.
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.
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."

Responsibilities

Lead Commercial Deal Strategy: Own the commercial architecture for Applecart. Serve as the strategic partner and mandatory final sign-off for all proposals, ensuring options presented to clients make strategic sense.
Bespoke Enterprise Structuring & Storytelling: Partner with the BD team to architect highly complex deals. Translate novel product capabilities and modern pricing models (including usage-based metrics, tokens, and credits) into compelling, C-suite-ready value narratives.
Craft the Visual Deal Narrative: Directly own the creation and design of high-impact pricing proposal slides for all major deals. You will translate complex financial options, data models, and usage-based value into beautifully simple, executive-ready slides that the BD team can easily deliver to C-suite buyers.
Establish Commercial Guardrails: Create the strategic frameworks that allow the sales team to move fast and remain creative without breaking our unit economics. Act as a high-stakes gatekeeper who can confidently collaborate on a better way to get a complex deal done.
Cross-Functional Leadership: Command presence and build deep trust with internal stakeholders across Sales, Operations, Legal, Finance, and Executive Leadership to drive complex deals across the finish line.
Pattern Recognition & Playbooks: Analyze won and lost deals to identify trends. Codify these patterns into an evolving, versatile commercial playbook that scales our collective deal intuition.
Pricing Integration: Oversee global pricing models and calculators, stress-testing our margins and subscription projections against real-world performance to ensure they align with our broader deal-making strategy.