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 current 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 new 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.

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