Since our beginnings in 2009, the world of commerce has evolved tremendously. So has Square. After enabling everyone to accept payments and never miss a sale, we noticed that merchants were being slowed down by disparate and obsolete products and tools that do not work harmoniously.

We therefore set out to develop software and created integrated, omnichannel solutions to help merchants sell online, manage their inventory, offer "Buy Now, Pay Later" functionality, schedule appointments, build customer loyalty, and hire and pay their employees. Throughout all of this, we have integrated financial services tools into the point-of-sale system, so that merchants can access a business loan and manage their cash flow in one place. Afterpay contributes to our goal of providing omnichannel tools that generate significant value and growth, allowing merchants to attract the next generation of shoppers, increase order volume, and be competitive on a larger scale.

Today, we are the partner of businesses of all sizes, from large companies with complex operations to sellers just starting out, as well as merchants who began selling with Square and have grown over time. Our solutions evolve at the same pace as our merchants. An incredible opportunity lies before us. We are building an important, meaningful, and sustainable company, and we are helping merchants around the world do the same.

The Role

At Square, we are reinventing the way small and medium-sized businesses grow. As an SMB Account Executive, you will convert high-quality interested leads into long-term customers, while also sourcing your own opportunities to keep your pipeline full. You will be at the heart of our growth engine: fast-paced, metrics-driven, and designed for people who set higher standards than the norm. This is the ideal role for people who don't wait to be told what to do, who don't make excuses, and who hold themselves to high standards.

If you are capable of closing sales by seizing the opportunities that come your way, enjoy solving real-world problems for businesses, and want to work hard in a dynamic environment where effort is directly rewarded with success, this role is for you.

Square offers the opportunity to thrive in a dynamic outbound prospecting environment, where your outreach allows you to offer Square's tools to a greater number of sellers, and where your success is part of our mission to provide fair conditions for entrepreneurs. We act quickly, we learn continuously, and we reward courage and results by offering unlimited earning potential.

Your Missions

Manage the entire sales cycle, from the first exchange to contract closure, with SMB merchants across various industries.
Engage and convert a steady stream of interested leads from marketing, partnerships, or those who have expressed interest in our products.
Generate a significant portion of your pipeline through prospecting. You relentlessly build your pipeline through prospecting: you don't rely on incoming requests, you take the lead. You know how to identify new opportunities, develop a personalized approach, and create demand where there was none.
Act with diligence at every stage: you effectively manage time and priorities in a high-volume environment. You act quickly and do not let opportunities stagnate.
Understand customer pain points and propose consultative, value-based solutions that have a measurable impact. You diagnose real business problems and take charge of solving them.
Collaborate with teams (Onboarding, Product, Marketing, and Support) to ensure a seamless customer experience and a continuous feedback loop.
Track and forecast your pipeline accurately in Salesforce: you are data-driven and use metrics to improve your performance.
Consistently meet and exceed monthly and quarterly revenue targets.
Raise the bar every quarter: you improve conversion rates, contract values, and activity without being asked.
Bounce back from obstacles: when negotiations get complicated, you double your efforts.

You Have

1 to 2 years of experience in remote sales or full-cycle contract negotiation, ideally in a fast-paced SaaS, payment, or SMB-focused environment.
A proven ability to exceed quotas and close contracts in a context of short sales cycles with high transaction volume.
Strong communication skills over the phone, video, and in writing: you quickly build trust and move contracts forward decisively.
A true hunter mindset: a mentality focused on disciplined prospecting, which allows you to create and accelerate the pipeline independently of incoming requests.
Curiosity and empathy: you look into the customer's business, discover their real needs, and confidently propose the right solution.
An ability to thrive in ambiguity: you demonstrate motivation and have a thirst for learning and growth.
Proficiency in a CRM (Salesforce or equivalent) 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.
An ability to sell in both French and English.

Block takes a market-based approach to compensation, which may vary depending on the work location. In Canada, sites are divided into two zones based on a labor cost index specific to each geographic zone. The starting compensation for the successful candidate will be determined based on their skills related to the role, experience, qualifications, work location, and market conditions. These ranges are subject to change in the future.

The total compensation for this role is:

$86,000—$129,000 CAD

Application Guidelines

Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.

Use of AI in Our Hiring Process

We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

SMB Account Executive

You Have

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