Hopper is hiring a Founding Enterprise Sales Lead, AI (100% Remote - San Francisco or NYC)

About the Role We are seeking a pioneering Enterprise Account Executive to spearhead our initial wave of HTS Assist enterprise transactions and validate our global market penetration approach from initial contact through implementation. This role demands comprehensive ownership of the entire enterprise lifecycle, spanning discovery, pilot design, commercial negotiations, security assessments, and transformation into long-term production agreements. It represents a foundational 0-to-1 position integrating enterprise sales, market strategy, solution architecture, and meticulous operational execution, requiring substantial autonomy and strategic ownership. HTS Assist represents our conversational AI customer service platform specialized for travel and hospitality sectors. The solution automates high-volume interaction scenarios like itinerary modifications, refund processing, cancellations, and disruption management, seamlessly integrating with existing communication platforms to deliver reliable automation with smooth human intervention capabilities. Daily Responsibilities: Enterprise Sales Execution - Manage comprehensive enterprise sales processes across airlines and major corporate entities - Drive comprehensive opportunity identification and deal progression - Develop pipeline through strategic outreach, partnership channels, and executive networking Go-to-Market Strategy & Team Development - Collaborate in designing initial market penetration strategies, pricing frameworks, and operational playbooks - Prepare to construct and lead future sales organizational structures globally Pilot Design & Conversion - Architect pilots demonstrating clear pathways to scalable, multi-year production agreements - Establish precise success metrics encompassing automation rates, resolution times, and customer satisfaction parameters Commercial & Operational Navigation - Expertly manage complex procurement, legal, and information security processes - Negotiate statements of work connecting pilot outcomes to production commitments - Structure pricing models ensuring sustainable economics and clear expansion pathways Customer Advocacy & Executive Engagement - Secure landmark customer wins and develop executive relationship strategies - Transform early adopters into compelling reference cases Ideal Candidate Profile: - 5-10 years enterprise sales experience in high-growth SaaS/AI environments - Proven track record launching novel market approaches - Consistent multi-million dollar contract closer - Demonstrated expertise in AI consumption pricing models - Strong value engineering capabilities - Executive-level communication proficiency - Self-motivated with high entrepreneurial agency - Flexible across international time zones Organizational Benefits: - Competitive compensation package - Uncapped performance bonuses - Unlimited PTO - Comprehensive healthcare coverage - Equity opportunities - Entrepreneurial work culture - Flexible work arrangements Compensation Range: $400K - $500K