Head of AI Sales - Enterprise
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 data annotation, synthetic data, or ML training data productsDeep functional understanding of machine learning workflows — model training, data pipelines, MLOps, and the infrastructure that supports themAbility to engage credibly at the CTO, VP of AI/ML, and Chief Data Officer levelExperience navigating long, complex sales cycles (6–18 months) with multiple stakeholders and procurement gatekeepersStrong analytical instincts — you're comfortable in CRM and building your own pipeline forecastsThis is a Boston-based position. Nice to HaveRelationships within AI/ML teams at major cloud providers, financial institutions, and/or retailBackground in technical pre-sales or solutions engineeringIncentivesCompetitive package + 100% healthcare and dentalAMAZING commission structureAttractive equity packageMust be authorized to work in the US. No visa sponsorship.If you are a fit, send us an email with your resume at contact@waffle-labs.com