Senior Account Executive, Mid-Market at Block. About the role Join the Square team to help mid-market businesses scale through our integrated commerce ecosystem. You will manage the entire sales process, identifying new opportunities and closing complex deals that require a consultative approach.
Key facts Location: Toronto, Ontario, Canada
Engagement: Full-time
Salary: 152,300 - 228,500 CAD OTE
Team: Mid-Market
What you’ll do Manage the end-to-end outbound sales cycle, from initial prospecting to final contract negotiation.
Create a robust sales pipeline using cold outreach, social selling, and targeted campaigns.
Design custom, multi-product solutions that address the specific operational needs of merchants.
Work alongside Business Development teams while independently securing new business.
Lead discovery sessions, product demonstrations, and negotiations with multiple stakeholders.
Coordinate with Product, Marketing, Implementation, and Operations teams to ensure successful solution delivery.
Maintain accurate forecasting and data hygiene within Salesforce.
Meet or exceed monthly and quarterly revenue targets.




Requirements 3+ years of experience in full-cycle B2B sales with a history of hitting quotas.
Demonstrated success in outbound prospecting and acquiring recent business, ideally within SaaS or fintech.
Experience managing complex, multi-threaded sales cycles.
Ability to generate pipeline from the ground up through strategic outreach.
Strong verbal, written, and presentation skills.
Proficiency in consultative selling and diagnosing business challenges.
BA/BS degree or equivalent practical experience.
Fluency in both French and English.
Advanced skills in Salesforce and modern sales software.
Practical notes Compensation is market-based and determined by skills, experience, and location.
You may submit up to 9 active applications within a 60-day window.
Reapplications for this role are permitted 90 days after a previous review.
The hiring process may utilize automated AI tools for application evaluation.
Benefits include remote work options, medical insurance, flexible time off, retirement savings, and family planning support.

#J-18808-Ljbffr

📌 Senior Account Executive, Mid-Market (Ontario)
🏢 Block
📍 Ontario