SMB Account Executive - Canada

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,  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.

The Role

At Square, we’re re-imagining how small and midsize businesses grow. As an SMB Account Executive, you’ll convert high-quality inbound leads into long-term customers — while also sourcing your own opportunities to keep your pipeline full. You’ll be at the heart of our growth engine: fast-paced, metrics-obsessed, and built for people who hold themselves to a higher bar than anyone else will. This is a role for people who don’t wait for direction, don’t make excuses, and don’t settle for “good enough”. 

If you’re a closer who thrives on momentum, loves solving problems for real businesses, and wants to work hard in a high-energy environment where effort translates directly into success — this is your role.

Square offers the opportunity to operate in a fast-paced outbound environment where your outreach brings Square’s tools to more sellers - and your success becomes part of our mission to level the playing field for entrepreneurs. We move fast, learn continuously, and reward grit and results by offering uncapped earning potential.

You Will

• Own the full sales cycle — from first conversation to close — with SMB merchants across a variety of industries.
  
  


• Engage and convert a steady flow of warm inbound leads from marketing, partnerships, and product interest.
  
  


• Generate a meaningful portion of your pipeline through outbound. You relentlessly build your pipeline through outbound prospecting — you don’t rely on inbound, you outwork it. You know how to identify new opportunities, craft personalized outreach, and create demand where none existed.
  
  


• Operate with urgency across every stage - — you manage time and priorities effectively in a high-volume environment. You move fast, and don’t let deals stall.
  
  


• Understand customer pain points and deliver value-based, consultative solutions that drive measurable impact. You diagnose real business problems and take ownership of solving them.
  
  


• Collaborate across teams (Onboarding, Product, Marketing, and Support) to ensure a seamless customer experience and continuous feedback loop.
  
  


• Track and forecast your pipeline accurately in Salesforce — you’re data-driven and use metrics to improve performance.
  
  


• Consistently hit and exceed monthly and quarterly revenue goals.

• Raise your own bar every quarter - improving conversion rates, deal size, and activity without being asked.

• Turn Obstacles into momentum - when deals get hard, you get sharper.
  
  

You Have

• 1-2 years of inside sales or full-cycle closing experience, ideally in a fast-paced SaaS, payments, or SMB-focused environment.
  
  


• Proven ability to exceed quota and close business in a high-volume, short-cycle motion.
  
  


• Strong phone, video, and written communication skills — you build trust fast and move deals forward decisively.
  
  


• A true hunter mentality -  A hunter’s mindset focused on disciplined outbound outreach, allowing you to build and accelerate pipeline independent of inbound demand


• Curiosity and empathy: you dig into the customer’s business, uncover real needs, and position the right solution with confidence.
  
  


• Ability to thrive in ambiguity — you’re self-motivated, coachable, and hungry to grow.
  
  


• CRM fluency (Salesforce or similar) and a data-driven approach to activity management.
  
  


• High standards for yourself and your team -  — you celebrate wins together, share what works, and raise the bar for those around you.


• Ability to sell in French and English