Sales Representative

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 a fast growing AI solutions agency focused on delivering practical, results-driven solutions for clients across diverse industries. The company emphasizes collaboration, accountability, and clear communication to help partners achieve measurable business outcomes. Team members are encouraged to bring forward ideas, work independently when needed, and contribute to a culture of continuous improvement.

Role Description

As a Sales Representative at Idle Work, you will own the full customer journey for owner-operated small businesses across Long Island and the five boroughs. That runs from the first walk-in conversation, through signing, to the day the customer is live and relying on their AI employee.

This is a field-first role. You will meet business owners at their counters, understand how their day actually runs, and show them what an AI employee can take off their plate. You will work directly with the founder and the engineering team, own your territory, and have a visible hand in how Idle Work sells, onboards, and grows accounts as we scale.

What You'll Do

• Own the end-to-end sales cycle for small business accounts: prospecting, in-person discovery, live demos, and closing.
• Build and work a territory across Long Island and NYC, focusing on retail, convenience, restaurants, gas stations, and other owner-operated businesses.
• Run discovery conversations that uncover real operational pain, such as inventory, reordering, scheduling, customer messages, and bookkeeping, and map it to the right Idle Work role.
• Deliver tailored demos, in person and virtually, that show owners exactly what their AI employee will do on day one.
• Lead onboarding for every account you sign, partnering with Engineering until each customer is live and actively using the product.
• Serve as the primary point of contact for your accounts through regular check-ins and fast issue resolution.
• Expand existing accounts with additional roles, and turn satisfied customers into referrals and introductions.
• Maintain accurate pipeline, demo, signup, and retention data in the CRM, and report on territory and account performance.
• Bring structured, written feedback from the field to shape product, pricing, and process.

What You'll Bring

• 2+ years of closing experience in SMB sales, field sales, or account management. Software, SaaS, payments, or POS experience is a strong plus.
• A track record of meeting business owners face to face and following up until there is a clear yes or no.
• Strong discovery skills. You ask good questions, listen closely, and can explain a technical product in plain language.
• Excellent organization. You close loops, keep records current, and manage a full pipeline without dropping follow-ups.
• Comfort with negotiation and with handling objections from busy, practical owners.
• Confidence running product demos, in person and virtual, and working in CRM and productivity tools.
• Self-direction and results focus, working well in a hybrid setup without a central office.
• A home base in the New York City metro area, with reliable transportation to customer locations across Long Island and the five boroughs.
• A bachelor's degree in Business, Marketing, Communications, or a related field, or equivalent practical experience.

Nice to Have

• Experience selling to owner-operated businesses such as convenience stores, delis, restaurants, gas stations, or retail shops.
• A background in customer onboarding, customer success, or account management for a software or service product.
• Familiarity with POS systems, small business bookkeeping tools, or messaging platforms like WhatsApp Business.
• Experience at an early-stage company where you owned a territory and a number.
• Fluency in a second language common among NYC and Long Island small business owners.

Compensation

• Base pay of $25,000 - $50,000 per year, depending on experience.
• Commission on top of base, tied to demos booked, businesses signed, and clients retained through onboarding.
• On-target earnings of $72,000 - $100,000 per year.

Why Idle Work

You will be putting AI to work for the businesses that keep New York running: the corner stores, delis, and local shops that rarely get technology built for them. The product is live, the pricing is simple, and owners can try it before they commit, which makes it a product you can sell with confidence. You will have direct access to the founder, real ownership of your territory, and a visible hand in shaping how the company grows. There is also a path into a management role as we expand to other cities and states.

Idle Work provides equal employment opportunities to all applicants and employees without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran status, or disability.