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

About the Job

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.

The Product: HTS Assist

HTS Assist is our conversational AI customer service platform for travel and hospitality. It automates high volume intents like itinerary changes, refunds, cancellations and disruption handling, Assist 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 like:

Enterprise Sales Execution

• 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

GTM Strategy & Team Buildout

• 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
  

Pilot Design & Conversion

• 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
  

Commercial & Legal Navigation

• 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
  

Customer Advocacy & Executive Engagement

• Land referenceable wins and drive executive engagement strategies, including case studies and C-level sponsorship
  

• Convert early adopters into compelling references and case studies

The ideal candidate has:

• 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

  
  Perks and benefits of working with us:

• 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.

  More about Hopper/ HTS

  At 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 massive amounts of data and advanced machine learning algorithms, Hopper combines its world-class travel agency offering with proprietary fintech products to bring transparency, flexibility and savings to travelers globally. We have developed several unique fintech solutions that address everything from pricing volatility to trip disruptions – helping people travel better and save more on their trips.

  The Hopper platform serves hundreds of millions of travelers globally and continues to capture market share around the world. he Hopper app has been downloaded over 120 million times and has become largely popular among younger travelers – with 70% of its users being Gen Z and millennials.

  While everyone knows us as the Gen Z and Millennial travel app, Hopper has evolved to become much more than that. In recent years, we’ve grown into a travel fintech provider, commerce platform, and global travel agency that powers some of the world’s largest brands.

  Through HTS, our B2B division, the company supercharges its partners’ direct channels by integrating our fintech products on their sites or powering end-to-end travel portals. Today, our partners include leading travel brands like Capital One, Nubank, Air Canada, and many more.

  Here are just a few stats that demonstrate the company’s recent growth:

  • Billions of dollars worth of travel and travel fintech are sold through Hopper and HTS’ channels every year.

  • Our fintech products – including Cancel for Any Reason and Flight Disruption Assistance – have exceptionally strong CSAT because the terms are always clear, and customers receive instant, no-questions-asked resolutions.

  • Almost 30% of our app customers purchase at least one fintech product when making a booking; and consumers are 1.6x more likely to repurchase if they add fintech to their booking vs if they booked just travel.

  Given the success of its fintech products, Hopper launched a B2B initiative, HTS (Hopper Technology Solutions), which represents more than 75% of the business.

  Through HTS, any travel provider (airlines, hotels, banks, travel agencies, etc.) can integrate and seamlessly distribute Hopper’s fintech or travel inventory on their direct channels. As its first HTS partnership, the company partnered with Capital One to co-develop Capital One Travel, a new travel portal designed specifically for cardholders. Other HTS partners include Air Canada, Uber, CommBank, Nubank, Flair Airlines and many more.

  Hopper has been named the #1 most innovative company in travel by Fast Company Hopper has been downloaded over 120 million times and continues to have millions of new installs each month. Hopper is now the #3 largest online travel agencies in North America and 70% of our app customers are Gen-Z and millennials travelers.

  Hopper has raised over $750 million USD of private capital and is backed by some of the largest institutional investors and banks in the world. HTS is primed to continue its growth as the leading travel ecommerce provider in a $1 trillion online shopping category. The Hopper app and website will also continue to be the preferred travel provider for Gen Z and Millennials..

  Come take off with us!
  
  #LI-REMOTE