Head of Deal Strategy

Applecart; New York (NY); On-site; USD 180,000 - 200,000; Full time

Job summary

Applecart is seeking a Head of Deal Strategy for its New York City office. This hybrid role will require ownership of the commercial architecture for proposals and engaging with seasoned Business Development teams to secure new clients.

The ideal candidate will have at least 6 years of experience in Deal Strategy within the software or consulting industries, a proven track record with complex enterprise deals, and exceptional communication skills for C-suite interactions.

The compensation package includes a base salary ranging from $180,000 to $200,000 plus bonuses and equity.

Qualifications

• 6 years of experience leading Deal Strategy or Revenue Operations in software or consulting.
• Proven experience structuring complex, bespoke Enterprise deals.
• Exceptional communication skills for C-suite-level presentations.
• Experience with usage-based or consumption monetization models.
• Ability to thrive in a high-growth, fast-paced environment.

Responsibilities

• Own the commercial architecture and structure of all proposals.
• Partner with BD to create value narratives for complex deals.
• Design high-impact pricing proposal slides for major deals.
• Establish strategic frameworks for sales team deal-making.
• Analyze deal patterns and create a commercial playbook.
• Oversee global pricing models and stress-test rental projections.

Skills

Enterprise Deal Strategy Background

Enterprise-Level Commercial Track Record

Versatility Across Industries

Novel Pricing Familiarity

High Executive Presence & Drive

Thriving in Ambiguity

Strategic Intuition & Visual Communication

Job description

About The Role

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, and we are looking for a commercial strategist to turn our leadership team’s mental model 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.

What You’ll Do

• 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. 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.

Experiences And Capabilities You Bring

• 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.
• 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.
• Versatility Across Industries: A proven track record of success across multiple industries or distinct product verticals, demonstrating agility to quickly learn a new space, understand varying buyer psychologies, and adapt commercial strategies.
• 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.
• 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.
• Thriving in Ambiguity: A strong desire and demonstrated ability to operate successfully in a high-growth, fast-paced, and fluid entrepreneurial environment. Comfortable building the framework while executing the strategy.
• Strategic Intuition & Visual Communication: 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".

Logistics & Compensation

This is a hybrid role. Work from home on Monday and Friday and in Applecart’s New York City office Tuesday through Thursday.

Our compensation package consists of three components: a base salary, an annual cash bonus, and generous equity compensation. The base salary range for this role is between $180,000 and $200,000, based on the candidate’s experience and skills relative to the requirements listed above. The salary range is exclusive of discretionary annual cash bonus and equity compensation and is specific to candidates located in the New York City area.