Head of Go-to-Market

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 Go-to-Market (GTM) Enablement in our New York office.

About the Role:

As a leader on the go-to-market team, the Head of GTM Enablement will be responsible for building the foundation of the onboarding, training, and continuing education programs for the company’s GTM organization. To continue in our fast-paced growth, you will play a crucial role leading the development and implementation of a robust onboarding, training and continuing education program for a rapidly growing team of sellers, Client Services professionals, and marketing teams. You also will work closely with Product Marketing in connection with the development of and updates to internal training and customer-facing collateral as we expand to new buyer personas and roll out new products and features. You will be responsible for identifying gaps in existing training and collateral and developing content and programming to fill them. You will leverage performance data and conversation intelligence to identify areas of opportunity for training and development.

In this position, you will report to the Co-CEO and Co-Founder, Matt Kalmans, and will work closely with executive leadership (including our Co-CEO and Co-Founder) and members of the Business Development, Product, Client Services, Marketing, and Revenue Operations teams. This role is initially an individual contributor role that will receive support from other Revenue Operations team members, but will have the opportunity to build and lead a team over time as the company grows.

What You’ll Do:

• Own the new hire onboarding program for the go-to-market team, including Sales, Client Services, and Marketing:
• Oversee the establishment of the foundational onboarding, training, and certification programs for the GTM organization
• Iterate and improve upon the existing training curriculum for go-to-market roles to improve ramp time and effectiveness
• Manage the new hire onboarding process and work with GTM leadership to verify new team members’ readiness to represent Applecart’s products and services to customers
• Manage training and certification of the GTM team for new product/feature rollouts and new process rollouts
• Collaborate with stakeholders from Product, Product Marketing, Sales, and Client Services to develop the appropriate training and certification programs for new products or features
• Collaborate with GTM leadership and Revenue Operations to develop training and certification programs for customer-facing processes and skills
• Own the outcomes of the training programs you manage: continually measure program completion, participant performance, and business impact of each program
• Observe customer meetings and embed with the GTM team as needed to develop an independent perspective on necessary collateral and training
• Using performance data and conversation intelligence tools, collaborate with revenue leadership to identify knowledge and skills gaps across the GTM team, and build continuing education strategies to close those gaps
• Collaborate with the Product Marketing team to develop a communication strategy and calendar for effectively enabling the GTM team throughout the year and managing new product and feature rollouts
• Partner with Revenue Operations to source, implement, manage, and train on technologies that drive productivity for the GTM team

Experiences and Capabilities You Bring:

• Significant experience in revenue/sales enablement, ideally at fast-growing B2B technology-enabled services or software companies that sell complex, high-ACV solutions to C-level buyers
• Experience building a foundational GTM enablement program from the ground up - you ideally have helped lead the transition from founder-led sales to a scalable GTM model from an enablement perspective
• Strong understanding of the sales ecosystem, including sales processes, methodologies (ie. MEDDIC or other similar sales methodologies), content, tools, and trainings
• Demonstrated excellence in development and design of sales collateral (presentations, templates, one-pagers, standard email copy, etc.)
• Experience managing GTM employee training and onboarding programs
• Instructional design training and experience
• Expertise in key software in the sales tech stack, including:
• CRM software like HubSpot or Salesforce
• Conversation intelligence tools like Gong or Chorus
• Knowledge management platforms like Confluence
• Presentation software like PowerPoint or Google Slides
• Shared drive software like Google Drive or Sharepoint

This is a hybrid role. Work from home or in the office 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 $200,000 - $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.