Head of Deal Strategy

About the role

The Head of Deal Strategy at Applecart will lead the commercial architecture for the company. They will serve as the strategic partner and final sign-off for all proposals, ensuring that each one is optimized to deliver maximum customer value while maintaining internal margin control. This role requires working 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 role is high impact, focusing on driving profitable revenue growth. The Head of Deal Strategy will also establish commercial guardrails, craft the visual deal narrative, and analyze won and lost deals to identify trends and codify them into a commercial playbook.

Responsibilities

• Lead Commercial Deal Strategy: Own the commercial architecture for Applecart. Ensure all proposals are strategically sound and present compelling value to C-suite decision makers.
• Bespoke Enterprise Structuring & Storytelling: Collaborate with the Business Development team to architect complex deals. Translate novel product capabilities and pricing models into compelling narratives for executive buyers.
• Craft the Visual Deal Narrative: Directly own the creation and design of high-impact pricing proposal slides. Ensure these slides are visually appealing and easy to understand for C-suite buyers.
• Establish Commercial Guardrails: Develop strategic frameworks to guide the sales team in moving efficiently and creatively while maintaining unit economics. Act as a gatekeeper for complex deals.
• Cross-Functional Leadership: Build trust and command presence with internal stakeholders across Sales, Operations, Legal, Finance, and Executive Leadership. Drive deals through to completion.
• Pattern Recognition & Playbooks: Analyze won and lost deals to identify trends and codify these into an evolving commercial playbook that scales Applecart’s deal-making intuition.
• Pricing Integration: Oversee global pricing models and calculators. Stress-test these models against real-world performance to ensure they align with the broader deal-making strategy.

Requirements

• 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 the agility to quickly learn a new space 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 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.

Qualifications

• Experience in a similar role within a technology or SaaS company.
• Proven success in structuring and presenting complex deals to C-suite executives.
• Ability to translate technical concepts into clear, compelling narratives for executive buyers.
• Strong analytical skills to assess and optimize pricing models and proposals.
• Excellent interpersonal and communication skills to build trust and collaborate with cross-functional teams.
• Experience in creating and delivering high-impact pricing proposal slides.

Skills

• Strategic thinking and problem-solving skills.
• Ability to work independently and manage multiple projects simultaneously.
• Strong attention to detail and ability to handle complex financial models and data.
• Effective negotiation and closing skills for complex deals.
• Visual and verbal communication skills to present complex ideas clearly and persuasively.

Benefits

Applecart offers a competitive benefits package including health insurance, retirement plans, and paid time off.

Pay

The base salary range for this role is between $180,000 - $200,000, based on the candidate's experience and skills relative to the requirements listed above. The salary range provided is exclusive of discretionary annual cash bonus and equity compensation. The salary range provided for this role is specific to candidates located in the New York City area.

Schedule

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