Account Executive - Inside Sales

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.