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B2B Sales Specialist

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: Hello Gubby
Full Time, Commission-based only position
Listed on 2026-10-31
Job specializations:
  • Sales
    B2B Sales, Sales Representative, Business Development, SaaS Sales
Salary/Wage Range or Industry Benchmark: 21000 - 57000 USD Yearly USD 21000.00 57000.00 YEAR
Job Description & How to Apply Below

Job description:

Opportunity Type:
Independent Contractor / Freelance / B2B Sales Expert

Location:

Metro Vancouver, BC (Flexible / Remote & Field)

Compensation: 100% Commission-Based (25% to 40% Tiered Rates)

About Hello Gubby

Hello Gubby is the AI front desk for small businesses, and it’s growing into a full customer operations platform: the Intercom for small businesses.

One AI employee does the work of a whole front office. It answers calls like a receptionist, qualifies leads and books appointments like an SDR, greets website visitors with a video avatar, and follows up like a sales closer. It works 24/7 across phone, SMS, email, web chat, and video, with Whats App, Instagram, and Facebook rolling out next.

Small businesses lose customers every day to missed calls, slow replies, and follow-ups that never happen. Hello Gubby closes those gaps. Every call gets answered, every message gets a reply, every lead is captured, and every booking lands in the calendar, all without extra staff. It plugs into the tools businesses already use, like Go High Level , Hub Spot, and

Hello Gubby is built in Vancouver and is patent-pending, and is backed by notable US-based startup programs, and have been awarded with several recognitions. We serve customers across Canada and the US in industries like home services, cleaning, clinics, real estate, accounting, staffing, and trades.

The Opportunity

We are looking for self-motivated Independent B2B Sales Representatives across Metro Vancouver to bring Hello Gubby to local business owners. You’ll be selling into one of the fastest-growing categories in tech: AI that does real work for small businesses. As an Independent Sales Expert, you work on your own terms as a self-employed professional or business. You decide when, where, and how you prospect, run demos, and close deals.

This role can be your main source of income or a strong add-on to your existing sales work.

Why Hello Gubby?
  • Tiered Commission (25% to 40%):
    Earn competitive commission on your monthly collected sales.
  • Recurring Residual Income:
    Hello Gubby is a monthly subscription. As long as your clients stay subscribed and your contractor agreement is active, you earn recurring monthly commission on those accounts.
  • A Product That Sells Itself in Demos:
    Business owners can call the AI, text it, or email it and see the response in real time. One live demo does more than any pitch deck.
  • Grow With Your Accounts:
    Clients often start with phone and add SMS, email, web chat, and new channels over time. As their plans grow, so does your income.
  • No Quotas or Schedules:
    Full freedom over your hours, outreach, and working style.
  • Sales Tools Provided:
    Demo lines, pitch decks, product overviews, and sales collateral, plus direct support from the founder on bigger deals.
Key Activities
  • Identify and engage local business owners in Metro Vancouver (home care, cleaning, clinics, real estate, professional services, trades, and more).
  • Run online or in-person demos showing how Hello Gubby handles calls, texts, emails, and bookings.
  • Close subscription agreements and submit client details through our system.
  • Build ongoing relationships with your accounts to support renewals, upgrades, and referrals.
Compensation and Legal Structure
  • This is an Independent Contractor (100% commission) opportunity.
What We Look For
  • B2B Sales

    Experience:

    A background in lead generation, closing, or consultative selling. Experience in SaaS, AI, telecom, or local SMB sales is a strong asset.
  • Strong Communication and Demo

    Skills:

    Comfortable presenting in person or over video and explaining technology in simple terms.
  • Local Market Knowledge:
    An understanding of the Metro Vancouver small business landscape. An existing network of business owners is a big plus.
  • Self-Directed and Entrepreneurial:
    Able to work on your own, manage your pipeline, and thrive in a commission-based role.
  • Authorization to Work in Canada:
    Legally eligible to operate as an independent contractor in British Columbia.
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