Senior Account Executive, SMB

  • Full-time

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

The Square Canada Sales team is looking for an experienced Outside Sales Account Executive with drive, enthusiasm and a winning attitude to join our growing team. You will manage all stages of the deal cycle from sourcing to closing and will be comfortable selling an ecosystem solution across a broad range of industries - from retail to restaurants to professional services and more. Your sales and in-depth product expertise will guide Canadian businesses in their evaluation of our platform across a suite of software, hardware and embedded financial services to see if we are suited to solve the diverse challenges they face today. You will be focused primarily in the SMB/Mid-Market segment and will have prior experience sourcing, negotiating and closing complex deals in the Canadian market. This role is hybrid with expectations of spending a minimum of 1 day/week in our Toronto office.

You will:

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

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

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

  • As needed, meet prospects in the field and execute a face to face 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 

  • Act as an ongoing ambassador for Square introducing our products to merchants in all verticals: retail, food and drink, professional services, etc.

  • Oversee and project manage the sales cycle from prospect to close and partner with cross-functional partners to support with merchant needs

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

  • Have a keen attention to detail utilizing Salesforce to manage your pipeline, report on KPIs and provide accurate forecast data for Sales leadership 


You have:

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

  • 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 (e.g. hunting and cold calling) - this is essential 

  • An affinity for change; we like to try new things in order to improve  

  • Prior Salesforce experience or equivalent

Additional Information

Block takes a market-based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

Zone A: CAD $83,900.00
Zone B: CAD $80,800.00

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

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.



We want you to be well and thrive. Our global benefits package includes:

  • Healthcare coverage
  • Retirement Plans
  • Employee Stock Purchase Program
  • Wellness perks
  • Paid parental leave
  • Paid time off
  • Learning and Development resources

We’ve noticed a rise in recruiting impersonations across the industry, where individuals are sending fake job offer emails. Contact from any of our recruiters or employees will always come from an email address ending with,,, or,

Block, Inc. (NYSE: SQ) is a global technology company with a focus on financial services. Made up of Square, Cash App, Spiral, TIDAL, and TBD, we build tools to help more people access the economy. Square helps sellers run and grow their businesses with its integrated ecosystem of commerce solutions, business software, and banking services. With Cash App, anyone can easily send, spend, or invest their money in stocks or Bitcoin. Spiral (formerly Square Crypto) builds and funds free, open-source Bitcoin projects. Artists use TIDAL to help them succeed as entrepreneurs and connect more deeply with fans. TBD is building an open developer platform to make it easier to access Bitcoin and other blockchain technologies without having to go through an institution.

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