Founding Enterprise Account Executive, AI - Remote

Overview

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.

In Short

• Own the full enterprise sales motion end to end across airlines and other large enterprises.
• Lead outbound prospecting, opportunity qualification, and enterprise deal execution.
• Design and execute pilots that convert into scaled, multi-year production deals.
• Navigate complex procurement, legal, and InfoSec processes.
• Partner with Solutions Engineering for integrations with major platforms.
• Land referenceable wins and drive executive engagement strategies.
• 5–10 years in enterprise sales with a record of closing complex deals.
• Consistent record of closing multimillion-dollar annual quotas.
• Skilled in value engineering and building ROI cases tied to automation rates.
• Self-directed builder with high agency who thrives in prospecting and negotiation.

Requirements

• 5–10 years in enterprise sales with a record of closing complex, multi-stakeholder deals.
• Proven 0-to-1 experience launching a new motion or region.
• Comfortable with $3M+ TCV and $1M+ ARR equivalents.
• At least two examples of converting a paid pilot into a multi-year contract.
• Pricing and negotiation depth in AI consumption models.
• Executive presence with comfort selling to C-level.
• Time-zone flexibility across the Americas and Europe.

Benefits

• Competitive salary and pre-IPO equity packages.
• Uncapped quarterly paid performance bonus.
• Unlimited PTO.
• Carrot Cash travel stipend.
• Access to co-working space on demand.
• Generous parental leave.
• 100% employer paid Medical, Dental and Vision coverage.
• Access to Disability & Life insurance.
• Health Reimbursement Account (HRA).
• Access to 401k plan.