Head of AI Sales - Enterprise

Waffle Labs
Boston, MAPosted May 7, 2026
Skip to main content Head of AI Sales - Enterprise Waffle Labs Boston, MA Apply Head of AI Sales - Enterprise Waffle Labs Boston, MA 2 months ago Over 200 applicants See who Waffle Labs has hired for this role Apply Save Report this job Use AI to assess how you fit Get AI-powered advice on this job and more exclusive features. Am I a good fit for this job? Tailor my resume Sign in to access AI-powered advices Email or phone Password Show Forgot password? Sign in Sign in with Email or New to LinkedIn? Join now By clicking Continue to join or sign in, you agree to LinkedIn’s User Agreement, Privacy Policy, and Cookie Policy. Sign in to evaluate your skills Email or phone Password Show Forgot password? Sign in Sign in with Email or New to LinkedIn? Join now By clicking Continue to join or sign in, you agree to LinkedIn’s User Agreement, Privacy Policy, and Cookie Policy. Sign in to tailor your resume Email or phone Password Show Forgot password? Sign in Sign in with Email or New to LinkedIn? Join now By clicking Continue to join or sign in, you agree to LinkedIn’s User Agreement, Privacy Policy, and Cookie Policy. Company DescriptionAn MIT spinoff, Waffle Labs is an AI research company at the forefront of developing the world’s most advanced Large Data Model. Powered by proprietary and large-scale anonymized data from various industries, Waffle Labs uncovers transformative insights. Founded in 2018, the company is supported by renowned partners, including Sony Innovation Fund, Barclays, Techstars, and BetterLabs Ventures. What You Will DoOwn the full enterprise revenue motion — from pipeline strategy through contract execution — targeting Fortune 500 and high-growth technology companiesDrive 7-figure and multi-year contract negotiations with sophisticated procurement, legal, and executive stakeholdersPartner closely with Product and Engineering to translate customer needs into roadmap priorities and winning proposalsBuild and refine sales playbooks, pricing frameworks, and competitive positioning strategiesReport directly to the CEO and Chief Data Scientist with full visibility into company strategyWhat You BringYou are a doer. 7+ years of enterprise sales experience, including 3+ years in a leadership role at an AI, ML, or data infrastructure companyDemonstrated track record of closing multiple $1M+ contracts with Fortune 500 or major public-sector organizationsPrior experience selling...

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