Founding Enterprise Sales Lead, AI Job at Hopper (San Francisco)

Job Description

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.

Job Responsibility

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

Requirements

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 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 is an asset
Fluency in the metrics that matter to CX leaders: containment, AHT, FCR, recontact rate, CSAT, cost per contact, staffing impact

What we offer

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
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

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Founding Enterprise Sales Lead, AI

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