Founding Enterprise Sales Lead, Hopper

• 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

Desirable

• We are hiring a founding Enterprise AE to own the first wave of HTS Assist enterprise deals and prove out our global go-to-market strategy from prospecting to production. You will own the entire enterprise cycle from discovery and pilot design through commercial negotiation, security diligence, and conversion to multi year production contracts
• This is a true 0 to 1 role that blends enterprise sales, GTM strategy, solution design, and rigorous operational follow through, requiring high autonomy and ownership. Success looks like repeatable pilot to production conversions, achievement of ACV targets with strong unit economics, and creation of referenceable customers
• Once the initial GTM phase is proven, the goal is to expand and lead a global team to scale the motion worldwide and establish category leadership
• 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
• Shape the 0-to-1 GTM strategy, pricing frameworks, and playbook design in collaboration with Leadership, Product, Marketing, and RevOps
• Once the GTM motion is proven, build and lead the future sales organization, hiring and coaching regional AEs and SDRs to scale the model globally
• 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
• Navigate complex procurement, legal, and InfoSec processes with credibility
• 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
• Land referenceable wins and drive executive engagement strategies, including case studies and C-level sponsorship
• Convert early adopters into compelling references and case studies