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About the Role

As a Senior Account Executive on our Mid-Market team, you will introduce Square's ecosystem to new sellers across various industries. You will build, shape, and drive your own pipeline, managing complex, multi-product deals from outreach to close, blending hunter instincts, consultative depth, and strategic execution.

Responsibilities

• Manage the full sales cycle, from prospecting to negotiation and closing, with mid-market businesses.
• Create and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative prospecting strategies.
• Develop multi-product solutions that span the entire Square ecosystem and tailor them to the specific needs of each merchant.
• Collaborate with Business Development on lead flow while independently driving new customer acquisition.
• Drive discovery, deliver impactful demos, and lead high-stakes negotiations within multi-party contracts.
• Serve as a trusted consultant and advisor, seamlessly taking on the responsibilities of a Business Development Manager, Account Executive, and Account Manager as needed.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations teams to deliver cohesive solutions.
• Maintain rigorous pipeline management and ensure forecast accuracy in Salesforce.
• Consistently meet and exceed revenue targets on a monthly and quarterly basis.

Requirements

• At least 3 years of experience in the full B2B sales cycle, with consistent quota attainment.
• Proven track record of prospecting and creating new business opportunities (preferably in SaaS or FinTech).
• Experience closing complex, long-cycle deals that require building relationships with multiple stakeholders.
• Ability to build a pipeline from scratch through targeted and strategic prospecting.
• Excellent communication, presentation, and negotiation skills, both over the phone, via video, and in writing.
• Strong consultative selling skills: diagnosing business challenges and crafting tailored solutions.
• A "scrappy" mentality: demonstrate resilience, creativity, and determination.
• Ability to work independently while contributing to a collaborative environment.
• Advanced proficiency in Salesforce and modern sales tools.
• A Bachelor's degree or equivalent experience.
• Ability to sell in both French and English.

Skills

• Salesforce
• Consultative Selling
• Prospecting
• Negotiation
• B2B Sales
• SaaS
• FinTech
• Social Selling
• Cold Outreach

Location

• Canada

Work Type

• Remote
• Full-time

Experience Level

• Senior

Education Level

• Bachelor's degree or equivalent experience

Salary/Compensations

• $152,300 - $228,500 CAD

Benefits

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

About the Company

• 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.

Equal Opportunity

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