The Grace Hopper Program at Fullstack Academy
Founding Enterprise Account Executive, AI (100% Remote - San Francisco or NYC)
The Grace Hopper Program at Fullstack Academy, San Francisco, California, United States, 94199
Overview
Founding Enterprise Account Executive, AI (100% Remote - San Francisco or NYC) for HTS (Hopper Technology Solutions) at The Grace Hopper Program at Fullstack Academy. This role owns the first wave of enterprise deals across airlines and large travel brands for HTS’ AI offering. It is a 0-to-1 role focused on proving our global go-to-market strategy and running the full enterprise sales cycle from prospecting through pilot design, legal/InfoSec diligence, negotiation, and conversion to multi-year production contracts. What you will do
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 mapping 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 What we’re looking for
5–10 years in enterprise sales with a track 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 (e.g., commit ramps, per-resolution or per-conversation pricing, minimums, multi-year terms tied 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; strong 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; willingness to travel as needed Nice to have: 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 Fluency in CX metrics: containment, AHT, FCR, recontact rate, CSAT, cost per contact, staffing impact Perks and benefits
Well-funded startup with large ambitions, competitive salary, and pre-IPO equity potential Uncapped quarterly paid performance bonus Unlimited PTO Carrot Cash travel stipend Access to co-working space on demand and work-from-home stipend Generous parental leave Entrepreneurial culture with open communication and high-impact collaboration 100% employer-paid Medical, Dental and Vision coverage Disability & Life insurance, Health Reimbursement Account (HRA), DCA/FSA, and 401k access About Hopper/ HTS
Hopper aims to become the leading travel platform globally, powering Hopper’s app, website, and HTS (Hopper Technology Solutions). We leverage data and ML to combine travel fintech products with a travel commerce platform, enabling transparency, flexibility, and savings for travelers. HTS partnerships include airlines, banks, and travel brands, enabling integration of Hopper’s fintech or travel inventory on partner channels.
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Founding Enterprise Account Executive, AI (100% Remote - San Francisco or NYC) for HTS (Hopper Technology Solutions) at The Grace Hopper Program at Fullstack Academy. This role owns the first wave of enterprise deals across airlines and large travel brands for HTS’ AI offering. It is a 0-to-1 role focused on proving our global go-to-market strategy and running the full enterprise sales cycle from prospecting through pilot design, legal/InfoSec diligence, negotiation, and conversion to multi-year production contracts. What you will do
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 mapping 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 What we’re looking for
5–10 years in enterprise sales with a track 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 (e.g., commit ramps, per-resolution or per-conversation pricing, minimums, multi-year terms tied 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; strong 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; willingness to travel as needed Nice to have: 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 Fluency in CX metrics: containment, AHT, FCR, recontact rate, CSAT, cost per contact, staffing impact Perks and benefits
Well-funded startup with large ambitions, competitive salary, and pre-IPO equity potential Uncapped quarterly paid performance bonus Unlimited PTO Carrot Cash travel stipend Access to co-working space on demand and work-from-home stipend Generous parental leave Entrepreneurial culture with open communication and high-impact collaboration 100% employer-paid Medical, Dental and Vision coverage Disability & Life insurance, Health Reimbursement Account (HRA), DCA/FSA, and 401k access About Hopper/ HTS
Hopper aims to become the leading travel platform globally, powering Hopper’s app, website, and HTS (Hopper Technology Solutions). We leverage data and ML to combine travel fintech products with a travel commerce platform, enabling transparency, flexibility, and savings for travelers. HTS partnerships include airlines, banks, and travel brands, enabling integration of Hopper’s fintech or travel inventory on partner channels.
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