Head of Deal Strategy

Job Description

Job Description

About Us

Applecart is the leading technology company that C-suites rely on to reach business-critical decision makers. The most important decisions are made by the hardest people to reach and influence. Historically, C-suite leaders have lacked the tools to reach the stakeholders who matter most to their business. The C-suites of hundreds of Fortune 500 companies, major agencies, trade associations, nonprofits, and governments use Applecart to put their best content in front of business-critical decision makers and those they trust — from policymakers and investors to CEOs, key employees, members of the media and more. Decision makers are informed by what they read, learn from advisors, hear from colleagues, and discuss with family and friends. To break through to them, you must reach them through the only channel that really moves them: those they know and trust. Applecart's platform uses publicly available data to map billions of social relationships between nearly every American adult and enable clients to deliver content directly to decision makers and those who matter most to them. 

We are hiring a Head of Deal Strategy in our New York City office.

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. 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.

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. 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.

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 the 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. You are comfortable building the framework while executing the strategy.
• 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."

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

Compensation:

Our compensation package consists of three components: (i) a base salary, (ii) annual cash bonus, and (iii) generous equity compensation.

The base salary range for this role is between $180,000-$250,000, 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.

A few facts about us:

• Applecart's platform has been used by hundreds of industry-leading clients spanning Fortune 500 companies like Blackstone and Intuit, leading nonprofit organizations like the Environmental Defense Fund, and top-tier advertising and communications agencies like Teneo, FGS, Weber Shandwick, and OMD. 
• Applecart is growing quickly — over the last 4 years, we've increased our revenue by 10X, grown our headcount by almost 5X, and we're cashflow positive. 
• Our senior leadership team includes two members of the Forbes 30 under 30 list for Marketing and Advertising, the former Head of Product at Moat, Oracle's online ad measurement platform, a former senior White House advisor, early sales and talent leaders from Google and Twitter, two of the Democratic Party's most successful pollsters and strategists, and alums of top-tier organizations like Bain & Company, Amazon and Simpson Thacher.
• Applecart raised a $100M Series C from Blackstone's tech growth fund at the end of 2025. The company's other investors include Bain & Company, global sports, entertainment and marketing giant Endeavor, KKR Co-Founder Henry Kravis, entrepreneur Chris Burch, a founder of Palantir, senior engineering leaders at Twitter and Yelp, former Fortune 50 and advertising agency CEOs, and a number of well-known venture capitalists. Ari Emanuel, CEO of TKO and Executive Chairman of WME, Wayne Berman, Blackstone's Head of Global Government Affairs, and Risa Heller, CEO of HELLER, serve on our board. 
• Our work has been featured on Morning Joe on MSNBC, BloombergTV, and The Colbert Report, and in Axios, Semafor, BusinessWeek, the Associated Press, Forbes, the Washington Post, and Politico, among many others.