Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together. So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff.

Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same. At Square, we’re re-imagining how mid-market businesses grow.

As a Senior Sales Account Executive on our Mid-Market Team, you’ll bring Square’s ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. Own the full outbound sales cycle — from prospecting to negotiation to close — with mid-market merchants. Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.

Partner with Business Development on lead flow while independently driving net-new logo acquisition. Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.



Maintain disciplined pipeline management and forecasting accuracy in Salesforce. 3+ years of full-cycle B2B sales experience with consistent quota achievement. ~ Proven success in outbound prospecting and net-recent business creation (SaaS or fintech preferred). ~ Experience closing complex, multi-threaded deals with longer sales cycles. ~ Ability to build pipeline from scratch using targeted, strategic outreach. ~ Exceptional communication, presentation, and negotiation skills across phone, video, and written channels. ~ A hunter’s mindset — resilient, creative, and driven to win. ~ Advanced proficiency with Salesforce and modern sales tools. ~ Ability to sell in both French and English.

Block takes a market-based approach to pay, and pay may vary depending on your location. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

OTE for this role is: $152,300 - $228,500 CAD These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws. Contact us here with hiring practice or data usage questions. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. Together, we’re helping build a financial system that is open to everyone.

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📌 Senior Account Executive, Mid-Market - Canada (Toronto)
🏢 Socket.dev
📍 Toronto