Founding Sales Leader - Build the AI Hotel Sales Engine

Stealth Vertical AI Startup; New York (NY); On-site; USD 150,000 - 260,000; Full time

Benefits offered by this job

Equity

High earning potential

Medical, dental, vision insurance

Lunch & fitness stipend

Office in Williamsburg

In-person, five days a week

Job summary

Autumn, a Brooklyn-based AI startup building an operating system for independent hotels, is seeking a Founding Sales Lead to shape its commercial organization from the ground up. You will personally close hotels each week and design the playbook, processes, metrics, tooling, and team that scale the motion.

You will hire, onboard, and coach the sales team, own the number, and report directly to the founders.

Qualifications

• 3–10 years in sales with high-velocity, short-cycle closes.
• Evidence of building or reshaping a sales motion at a startup.
• Experience coaching or leading reps and improving performance.
• Systems thinking: segmentation, metrics, and process design.
• Ability to automate repetitive work with AI and data-driven insights.

Responsibilities

• Close hotels personally every week in a high-velocity motion.
• Write the sales playbook: messaging, qualification, objections, follow-up.
• Run pipeline hygiene, forecasting, and weekly cadence.
• Set strategy on market segments, positioning, and demand pockets.
• Sharpen top-of-funnel with outbound messaging and feedback loops.
• Build and coach the sales team, set targets, and own outcomes.
• Provide market feedback to product and leadership on objections and pricing.
• Leverage AI to automate prep, follow-up, and admin tasks.

Skills

Sales experience

Quota attainment

System thinking

Leadership

Analytical

AI-driven selling

Job description

Autumn, a Brooklyn-based AI startup building an operating system for independent hotels, is seeking a Founding Sales Lead to shape its commercial organization from the ground up. You will personally close hotels each week and design the playbook, processes, metrics, tooling, and team that scale the motion.

You will hire, onboard, and coach the sales team, own the number, and report directly to the founders.