Founding Enterprise Account Executive, AI (100% Remote - San Francisco or NYC)

About the position 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 and educating the market, and positioning HTS’ AI solution as a must-buy for travel brands. Our 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.

Responsibilities

• Own the full enterprise sales motion end to end across airlines and other large enterprises, driving to multi-million ACV goals
• Lead outbound prospecting, opportunity qualification, and enterprise deal execution
• Build and advance pipeline through targeted outreach, partner channels, and executive networks
• Design and execute pilots that convert into scaled, multi-year production deals
• Define success criteria tied to automation rate, AHT, recontact, CSAT, and margin impact
• Secure data access, escalation paths, and change management plans with the customer
• Navigate complex procurement, legal, and InfoSec processes with credibility
• Lead InfoSec reviews, DPAs, and data residency discussions with enterprise buyers
• Negotiate and orchestrate SOWs that map pilot exit criteria to production commitments
• Structure pricing with durable economics, including consumption models, commit ramps, and multi-year terms with clear ROI and guardrails
• Protect gross margin while creating clear paths for expansion
• Partner with Solutions Engineering for integrations with Genesys, NICE, Five9, Talkdesk, Salesforce Service Cloud, or Zendesk
• Feed market insights to Product and Marketing to strengthen the playbook, collateral, and ROI models
• Land referenceable wins and drive executive engagement strategies, including case studies and C-level sponsorship
• Convert early adopters into compelling references and case studies

Requirements

• 5–10 years in enterprise sales with a record of closing complex, multi-stakeholder deals at high-growth SaaS or AI companies
• Proven 0-to-1 experience launching a new motion or region, including building pipeline, shaping pricing, and writing the early playbook
• Consistent record of closing multimillion-dollar annual quotas and multi-year contracts, comfortable with $3M+ TCV and $1M+ ARR equivalents
• At least two examples of converting a paid pilot into a multi-year production contract with defined success metrics and expansion path
• Pricing and negotiation depth in AI consumption models: commit ramps, per-resolution or per-conversation pricing, minimums, and multi-year terms aligned to ROI
• Skilled in value engineering and building ROI cases tied to automation rates and service cost reduction
• Executive presence with comfort selling to C-level, Operations, CX, IT, and Security, with clear written and verbal communication
• Self-directed builder with high agency who thrives in prospecting, discovery, pilot design, commercial negotiation, and internal orchestration without heavy SDR or SE coverage
• Time-zone flexibility across the Americas and Europe, with willingness to travel as needed

Nice-to-haves

• Experience 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 asset
• Fluency in the metrics that matter to CX leaders: containment, AHT, FCR, recontact rate, CSAT, cost per contact, staffing impact

Benefits

• Well-funded and proven startup with large ambitions, competitive salary, upsides of pre-IPO equity packages
• Uncapped quarterly paid performance bonus.
• Unlimited PTO.
• Carrot Cash travel stipend.
• Access to co-working space on demand through FlexDesk AND Work-from-home stipend.
• Please ask us about our very generous parental leave, much above industry standards!.
• Entrepreneurial culture where pushing limits and taking risks is everyday business.
• Open communication with management and company leadership.
• Small, dynamic teams = massive impact.
• 100% employer paid Medical, Dental and Vision coverage for employees.
• Access to Disability & Life insurance.
• Health Reimbursement Account (HRA).
• DCA/ FSA and access to 401k plan.

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