Jobs in Vaughan

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Within 25 km of Vaughan

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Account Executive - Inside Sales
Webware.ai
Toronto, ON

Webware.ai

Account Executive - Inside Sales

Toronto, ON, Canada

Full-time

Within 25 km of Vaughan · About 22.9 km from the city centre

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Job details

Job type: Full-time
Apply by: Apr 11, 2027
Posted: Oct 13, 2026

Original job description

Webware.ai | Toronto · Monday–Thursday in office, Fridays from home

CAD $110,000 OTE · Uncapped commission

You know how to close. Take the next step at Webware.ai.

We’re looking for an Account Executive who can lead a conversation with a business owner, demonstrate value, handle objections, and close the deal.

Previous experience personally closing sales is required.Bring a track record of results and work toward a Senior Account Executive role with CAD $148,000+ OTE, with a targeted promotion timeline of 6–9 months based on performance.

About Webware.ai

Webware.ai helps small businesses grow through an AI-powered sales and marketing platform combining websites, SEO, social media, reputation management, CRM, and marketing automation.

You’ll help business owners understand how these tools support their business and turn that understanding into a buying decision.

What you’ll do

Lead sales conversations with small business owners and decision-makers.

Understand their goals, challenges, and current marketing efforts.

Deliver product demos tailored to their needs.

Handle objections, communicate value, and confidently ask for the business.

Follow up consistently and close new customers.

Maintain your pipeline and deliver against sales targets.

Initially, you’ll book, run, and close your own opportunities. Inbound leads will become part of the mix later based on performance.

What we’re looking for

Proven closing experience: You’ve personally won business and can speak to your results against sales targets.

Strong sales judgment: You ask good questions, listen closely, and connect the solution to what matters to the buyer.

Confidence handling objections: You’re comfortable discussing price and helping buyers reach a decision.

Ownership and follow-through: You keep deals moving and take responsibility for your performance.

Coachability: You welcome feedback and apply it.

B2B sales experience is preferred, especially selling to small business owners. Digital marketing or software sales experience is a strong advantage, but isn’t required.

Earnings and career growth

CAD $110,000 on-target earnings, with uncapped commission.

Targeted progression to Senior Account Executive within 6–9 months**, based on demonstrated performance.

CAD $148,000+ OTE at the Senior Account Executive level.

Benefits included.

OTE reflects total earnings at target; actual earnings depend on sales performance.

Location and hours

Work from our Toronto office Monday–Thursday, and from home on Fridays.

Hours are 8:30 a.m.–5:00 p.m. ET, Monday–Friday.

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More about this job

Responsibilities

Lead sales conversations with small business owners, understand their goals and marketing needs, deliver tailored product demonstrations, handle objections, and close new customers. Manage and follow up on opportunities, maintain the sales pipeline, and meet sales targets.

Requirements

Candidates must have personally closed sales and be able to demonstrate results against sales targets. Strong sales judgment, objection-handling skills, ownership, follow-through, and coachability are required; B2B experience is preferred, while small-business, digital marketing, or software sales experience is advantageous.

Skills

Sales Closing
B2B Sales
Sales Conversations
Product Demonstrations
Objection Handling
Value Communication
Lead Follow-Up
Pipeline Management
Sales Target Achievement
Needs Assessment
Active Listening
Negotiation
Small Business Sales
Digital Marketing Sales
Software Sales
Coachability

Visa sponsorship

Not detected in the job text

Keywords

Webware.ai
AI-Powered Sales And Marketing Platform
Websites
SEO
Social Media
Reputation Management
CRM
Marketing Automation
Account Executive
Inside Sales
B2B Sales
Small Business Owners
Sales Closing
Product Demonstrations
Objection Handling
Sales Pipeline
Sales Targets
Inbound Leads
Digital Marketing
Software Sales
Uncapped Commission
Senior Account Executive

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