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Sales Account Executive

Job in Toronto, Ontario, M5A, Canada
Listing for: Square
Full Time position
Listed on 2026-03-11
Job specializations:
  • Sales
    Sales Development Rep/SDR, Sales Representative, Business Development, B2B Sales
  • Business
    Business Development
Job Description & How to Apply Below

Company Description

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality through Afterpay, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place.

Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

Job Description

Square is looking for a tenured Account Executive with a strong outbound sales background and winning attitude to join our Outside Sales Team. This role will work with all verticals. You will create your own outbound strategy in addition to working with the Business Development team to build a book of business. You will be expected to source leads, cold call and email them to generate interest and close deals selling our Square ecosystem to prospective merchants.

This role requires excellent communication skills, persistence, and a strong ability to build rapport with prospects to negotiate and close complex deals.

You will:

  • Understand the business and technology needs of a merchant to execute a sales motion using a consultative approach

  • Conduct prospecting, discovery, demos and develop a solution with first and third party offerings that best meets the prospects needs

  • As needed, go into the field and execute the sales motion to build strong relationships and increase win rates

  • Deliver a predictable, repeatable and scalable outbound sales process to fill your pipeline and close deals (activities include prospecting, cold calling, cold emailing, social selling, etc.)

  • Partner with our Business Development Team to convert and close cold, outbound leads

  • Lead the charge introducing Square to merchants in all verticals

  • Oversee the sales cycle from prospect to close and partner with other teams to ensure successful onboarding

  • Achieve and exceed monthly sales goals and key performance indicators (KPIs) through proactive outbound sales efforts

  • Partner with Product and Marketing teams to ensure our solutions meet the needs of the market

  • Use your prior sales experience to inform a creative go-to-market strategy

  • Utilize Salesforce to track, monitor, and report on sales activities, pipeline status, and outcomes

  • Qualifications

    You have:

  • 3+ years of sales experience in a full cycle closing role

  • A BA/BS degree or relevant experience

  • Experience exceeding sales targets, selling a diverse ecosystem of products, and closing complex deals

  • The ability to drive deals independently in a fast-paced, dynamic environment

  • Business development experience ( hunting and cold calling)

  • A collaborative and team player mentality

  • Prior Salesforce experience or equivalent

  • Ability to learn from and speak to multiple different industry stakeholders

  • Additional Information

    To find a location’s zone designation, please refer to this .

    We have listed some of our common hiring locations. Depending on the cost of labor in the relevant geographic area, state work locations that are approximately 50 Kilometers outside of the metro area listed may be aligned to a different zone. These zones may be modified in the future. Please speak with a recruiter for additional information.

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