Founding Enterprise Account Executive, AI (100% Remote ...

Founding Enterprise Account Executive, AI (100% Remote - San Francisco or NYC)Join to apply for the Founding Enterprise Account Executive, AI role at Hopper. We are hiring a Founding Enterprise Account Executive, AI to own the first wave of enterprise deals across airlines and large travel brands for HTS’ latest AI offering. This is a 0-to-1 role responsible for proving out our global go-to-market strategy, running the full enterprise sales cycle from prospecting through pilot design, legal/InfoSec diligence, negotiation, and conversion to multi-year production contracts.Success means repeatable pilot-to-production conversions, multi-million ACV wins with strong unit economics, and creation of referenceable customers. This role is not just about hitting revenue targets; it is about shaping how the travel industry thinks about customer experience, educating the market, and positioning HTS’ AI solution as a must-buy for travel brands.The ProductOur product is a conversational AI customer service platform for travel and hospitality. It automates high volume intents like itinerary changes, refunds, cancellations and disruption handling. It integrates with CCaaS platforms and core travel systems to deliver reliable automation with seamless human fallback. Outcomes include higher containment, faster resolution times, improved CSAT, and lower cost per contact.What Would Your Day-to-day Look LikeEnterprise Sales Execution: Own the full enterprise sales motion end to end across airlines and other large enterprises, driving to multi-million ACV goalsLead outbound prospecting, opportunity qualification, and enterprise deal executionBuild and advance pipeline through targeted outreach, partner channels, and executive networksPilot Design & ConversionDesign and execute pilots that convert into scaled, multi-year production dealsDefine success criteria tied to automation rate, AHT, recontact, CSAT, and margin impactSecure data access, escalation paths, and change management plans with the customerCommercial & Legal NavigationNavigate complex procurement, legal, and InfoSec processes with credibilityLead InfoSec reviews, DPAs, and data residency discussions with enterprise buyersNegotiate and orchestrate SOWs that map pilot exit criteria to production commitmentsStructure pricing with durable economics, including consumption models, commit ramps, and multi-year terms with clear ROI and guardrailsCross-Functional AlignmentPartner with Solutions Engineering for integrations with Genesys, NICE, Five9, Talkdesk, Salesforce Service Cloud, or ZendeskFeed market insights to Product and Marketing to strengthen the playbook, collateral, and ROI modelsCustomer Advocacy & Executive EngagementLand referenceable wins and drive executive engagement strategies, including case studies and C-level sponsorshipConvert early adopters into compelling references and case studiesAn ideal candidate hasMust haves5–10 years in enterprise sales with a record of closing complex, multi-stakeholder deals at high-growth SaaS or AI companiesProven 0-to-1 experience launching a new motion or region, including building pipeline, shaping pricing, and writing the early playbookConsistent record of closing multimillion-dollar annual quotas and multi-year contracts, comfortable with $3M+ TCV and $1M+ ARR equivalentsAt least two examples of converting a paid pilot into a multi-year production contract with defined success metrics and expansion pathPricing and negotiation depth in AI consumption models: commit ramps, per-resolution or per-conversation pricing, minimums, and multi-year terms aligned to ROISkilled in value engineering and building ROI cases tied to automation rates and service cost reductionExecutive presence with comfort selling to C-level, Operations, CX, IT, and Security, with clear written and verbal communicationSelf-directed builder with high agency who thrives in prospecting, discovery, pilot design, commercial negotiation, and internal orchestration without heavy SDR or SE coverageTime-zone flexibility across the Americas and Europe, with willingness to travel as neededNice to havesExperience selling to or partnering with CX, innovation, or operations leaders in travel, customer support, or digital transformation; familiarity with CCaaS, agent assist, or workflow automation is an assetFluency in the metrics that matter to CX leaders: containment, AHT, FCR, recontact rate, CSAT, cost per contact, staffing impactPerks and benefitsWell-funded and proven startup with large ambitions, competitive salary, upsides of pre-IPO equity packagesUncapped quarterly paid performance bonusUnlimited PTOCarrot Cash travel stipendAccess to co-working space on demand through FlexDesk and a work-from-home stipendGenerous parental leaveEntrepreneurial culture with open communication and small, dynamic teams100% employer paid Medical, Dental and Vision coverage for employeesDisability & Life insurance, Health Reimbursement Account (HRA), DCA/FSA and 401k accessMore About Hopper/ HTSAt Hopper, we are on a mission to become the leading travel platform globally – powering Hopper’s mobile app, website and our B2B business, HTS (Hopper Technology Solutions). By leveraging data and machine learning, Hopper combines travel with fintech products to bring transparency and savings to travelers. The Hopper platform serves hundreds of millions of travelers globally. The Hopper app has been downloaded over 120 million times, with a large share of Gen Z and millennials.HTS partners include Capital One, Air Canada, Nubank, and more. HTS represents more than 75% of the business. Hopper has raised over $750M and is backed by major investors. Compensation Range: $400K - $500K.Seniority levelMid-Senior levelEmployment typeFull-timeJob functionSales and Business DevelopmentIndustriesSoftware DevelopmentReferrals increase your chances of interviewing at Hopper. Get notified about new Enterprise Account Executive jobs in San Francisco, CA. #J-18808-Ljbffr

Created: 2025-09-17