Head of Deal Strategy

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 Head of Deal Strategy, you’ll design and build the pricing strategy and proposals behind Applecart’s most important deals. You’ll partner with senior members of our Sales team, who bring 20+ years of experience in public affairs, communications, and enterprise sales, to win new clients and grow existing partnerships. At Applecart, pricing is a strategic lever, not a static list. Every major engagement is tailored to the client and their specific needs. You’ll build those proposals, structuring options around each client’s goals and turn complex pricing into clear, executive ready slides our Sales team can present to C-suite buyers. You’ll also turn what’s working in our deals into a repeatable system of templates, frameworks, and playbooks. As the final sign-off on every client proposal, you’ll be responsible for ensuring each one delivers clear value while keeping our economics sound. Reporting to the SVP, Revenue Operations, you’ll work across Sales, BD, Operations, Legal, Finance, and Executive Leadership in a high-impact role driving Applecart’s revenue growth.

What You’ll Do :

Structure the proposals that win our biggest deals. Design and build the pricing proposal slides for every major Applecart deal. That means turning complex financial options, data models, and usage-based pricing into clear, executive-ready slides that our Sales team can use to convince C-suite buyers to partner with Applecart.

Balance commercial objectives and client strategy. Structure bespoke deal options that balance client needs with Applecart requirements, highlighting the value and trade-offs of each approach to support informed purchasing decisions.

Make novel pricing easy to buy. Translate new product capabilities and modern pricing models, including usage-based metrics, tokens, and credits, into value narratives executives can easily understand and support.

Own final sign-off on every proposal. Before any proposal goes to a client, you’ll confirm that the options make strategic sense, protect our margins, and set up the account for future growth.

Set guardrails that let sales move fast. Work with finance to set the discounting rules, deal frameworks, and approval thresholds that let Sales be creative without breaking our unit economics. When a deal doesn’t fit the rules, you’ll be the one who finds a better structure rather than just saying no.

Lead across functions. Earn the trust of Sales, Finance, Operations, and Executive Leadership, and you’ll hold your ground on pricing with senior stakeholders on both sides of the table.

Turn deal history into a playbook. Analyze won and lost deals, identify which structures and narratives actually work, and codify them into proposal templates and a commercial playbook the team can reuse.

Experiences and Capabilities You Bring :

Enterprise Deal Strategy Background: 8+ years of experience in 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 Sales 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.