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The Grace Hopper Program at Fullstack Academy

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

The Grace Hopper Program at Fullstack Academy, San Francisco, California, United States, 94199

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Founding Enterprise Account Executive, AI (100% Remote - San Francisco or NYC) Join to apply for the

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

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The Grace Hopper Program at Fullstack Academy

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, and 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

Generous parental leave, 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. The Hopper app has been downloaded over 120 million times and is 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.

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.

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!

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