Field Sales Executive — AI Solutions for NYC & LI SMBs

Idle Work Inc; New York (NY); Hybrid; USD 25,000 - 50,000; Full time

Job summary

Idle Work is seeking a Sales Representative to own the full customer journey for owner-operated businesses across Long Island and the five boroughs. You’ll meet owners in person, demonstrate the AI employee, and drive adoption from first contact to live operations.

This is a field-first role with hybrid flexibility, requiring strong closing skills, discovery, and ability to work with a small team to scale accounts as Idle Work grows.

Qualifications

• 2+ years closing SMB sales, field or account management.
• Bachelor's degree or equivalent practical experience.
• Strong discovery and qualification of business pain.
• Excellent organization and proactive follow-ups.
• Comfort negotiating with busy owners.

Responsibilities

• Own end-to-end sales cycle for small business accounts.
• Build territory across Long Island and NYC with retail, restaurants, and more.
• Run discovery calls to map pain to Idle Work roles.
• Deliver tailored demos in person and virtually.
• Lead onboarding and ensure customers go live and retained.
• Maintain CRM data and report on territory performance.

Skills

Closing deals

SMB sales

In-person sales

CRM proficiency

Negotiation

Product demos

Education

Bachelor's degree

Tools

CRM software

POS systems

Job description

Idle Work is seeking a Sales Representative to own the full customer journey for owner-operated businesses across Long Island and the five boroughs. You’ll meet owners in person, demonstrate the AI employee, and drive adoption from first contact to live operations.

This is a field-first role with hybrid flexibility, requiring strong closing skills, discovery, and ability to work with a small team to scale accounts as Idle Work grows.