Hopper · 1 day ago
Founding Enterprise Sales Lead, AI (100% Remote - San Francisco or NYC)
United States
Full-time
Remote
Senior Level
$400K/yr - $500K/yr
5+ years expHopper is on a mission to become the leading travel platform globally, and they are seeking a Founding Enterprise Sales Lead to own the first wave of HTS Assist enterprise deals. This role involves managing the entire enterprise sales cycle, from prospecting to production, and requires a strong focus on GTM strategy and team buildout.
AppsBig DataMobile AppsPredictive AnalyticsTravel
Responsibilities
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
Qualification
Required
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
Preferred
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
Benefits
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.
Company
Hopper
Hopper is a travel app that uses predictive analytics to make travel recommendations.
201-500 employees
H1B Sponsorship
Hopper has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (6)
2024 (6)
2023 (20)
2022 (28)
2021 (15)
2020 (6)
Funding
Current Stage
Late StageTotal Funding
$729.68MKey Investors
Capital One VenturesGPI CapitalWestCap
2022-11-07Series Unknown· $96M
2022-02-02Secondary Market· $35M
2021-08-17Series G· $175M
Leadership Team
Frederic Lalonde
Founder & CEO
Sebastien Rainville
Co-founder
Recent News
2025-12-05
2025-11-07
Stack Capital Group Inc.
2025-11-05
Company data provided by crunchbase