SMB Account Executive - Canada

Company Overview

Square, founded in 2009, has continually evolved in tandem with the changing commercial landscape. Beyond enabling seamless payment acceptance, Square has expanded to offer integrated, omnichannel software solutions that aid sellers in online selling, inventory control, appointment booking, loyalty engagement, workforce management, and embedded financial services enabling business loans and cash flow management. Afterpay further enhances these capabilities, helping sellers tap into the next generation of shoppers and scale effectively.

Role Summary

As a Small and Medium Business (SMB) Account Executive, you will be instrumental in transforming qualified inbound leads into loyal Square customers while actively sourcing new opportunities to maintain a robust sales pipeline. This high-energy, metrics-driven role demands individuals who pursue excellence independently, thrive under pressure, and consistently exceed expectations.

Key Responsibilities

• Manage the entire sales process from initial contact to deal closure with SMB clients across diverse sectors.
• Convert steady inbound leads from marketing, partnerships, and product interest into sales.
• Proactively generate pipeline through disciplined outbound prospecting using personalized outreach techniques.
• Operate with a sense of urgency to prevent deal stagnation and efficiently prioritize tasks in a high-volume setting.
• Diagnose customer challenges and deliver consultative, value-driven solutions that produce tangible business outcomes.
• Collaborate effectively with internal teams including Onboarding, Product, Marketing, and Support to ensure smooth client experiences and feedback integration.
• Maintain accurate sales forecasting and pipeline tracking through Salesforce, leveraging data insights to enhance performance.
• Consistently meet or exceed monthly and quarterly sales quotas.
• Continuously improve sales conversion rates, deal sizes, and activity levels autonomously.
• Approach challenges as opportunities to sharpen skills and maintain forward momentum.

Qualifications and Skills

• Between 1 and 2 years of experience in inside sales or full sales cycle closing, preferably within SaaS, payments, or SMB-focused industries.
• Demonstrated track record of surpassing sales targets in a fast-paced, short sales cycle environment.
• Exceptional communication skills across phone, video, and written formats, enabling rapid trust building and decisive deal progression.
• A proactive hunter mindset with discipline in outbound outreach, capable of independently generating and accelerating pipeline.
• Curiosity and empathy to deeply understand clients’ business needs and confidently position appropriate solutions.
• Ability to excel amid ambiguity, demonstrating self-motivation, coachability, and eagerness for personal growth.
• Proficiency with CRM platforms like Salesforce and a data-oriented approach to managing sales activities.
• High personal and team standards, fostering collaborative success and continuous improvement.
• Fluency in both French and English for effective communication.

Compensation and Benefits

Compensation is market-based and varies by geographic location within Canada according to a labor cost index. The expected on-target earnings (OTE) range from CAD 86,000 to CAD 129,000, depending on skills, experience, and job location. Comprehensive benefits include remote working options, medical insurance, flexible time off, retirement savings plans, family planning support, and more, designed to support your career success and personal life balance.

Additional Information

Square embraces automated AI tools in the hiring process, compliant with local regulations and privacy laws. Applicants should note specific guidelines for submitting applications and reapplications. This role is part of a broader group of companies building accessible financial and commerce technologies worldwide.