Outside Sales Representative – AI

Compensation: Commission-based with uncapped earnings ($100,000–$200,000+ potential)

About WeLevel

WeLevel is a fast-growing AI-powered sales and marketing platform built to help local businesses grow faster without adding headcount. Our technology ensures businesses never miss calls, respond instantly to leads, and convert more inquiries into booked appointments using Voice AI, chatbots, and automated follow-up systems.

We work with service-based businesses such as automotive repair & home services.

Position Overview

WeLevel is hiring motivated Outside Sales Representatives to introduce local businesses to cutting-edge AI and automation solutions. This is a consultative, relationship-driven sales role focused on showing business owners how AI can immediately increase revenue by capturing and converting missed opportunities.

You'll conduct in-person or phone-based outreach in an assigned territory, deliver short, value-focused pitches, and either close deals directly or set qualified appointments for inside closers, depending on the market.

This is a commission-only role with no cap and realistic six-figure earning potential for top performers.

What You'll Do

• Visit or call local businesses within your assigned territory
• Deliver short, consultative sales conversations focused on business impact
• Demonstrate WeLevel's AI Voice and Chatbot solutions
• Set qualified appointments or close new accounts
• Follow a structured daily sales plan and route assignments
• Track activity, notes, and outcomes in our CRM
• Collaborate with our onboarding and support teams to ensure client success

What You'll Get

• Uncapped commission with $100k–$200k+ earning potential
• Flexible schedule and control over your income
• Proven sales roadmap and daily route assignments
• Sales enablement tools, demos, and marketing materials
• Training, coaching, and ongoing support
• Entry into a fast-growing AI and automation company

Ideal Candidate

• Comfortable speaking with business owners and decision-makers
• Self-motivated, organized, and accountable
• Strong communication and relationship-building skills
• Prior experience in outside sales, B2B sales, door-to-door, marketing, advertising, SaaS, or lead generation is a plus (not required)
• Tech-curious and comfortable learning AI or software-based solutions
• Reliable transportation and ability to travel locally

Why Join WeLevel

• No cap on commissions—your income grows with your effort
• Daily local leads and structured sales support
• Fast-growing company redefining how small businesses grow with AI
• Supportive team culture with real advancement opportunities

Ready to take control of your income and help local businesses thrive with AI? Apply today and join WeLevel's expanding national sales team.

Job Type: Contract

Work Location: Hybrid remote in Chicago, IL