• 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
• 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
• 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
• 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
• 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

• Navigate complex procurement, legal, and InfoSec processes with credibility
• 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

Time-zone flexibility across the Americas and Europe, with willingness to travel as needed

• 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
• 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

• 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!
• 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