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 current 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.



5+ years of full‑cycle B2B sales experience with consistent quota achievement. ~ Proven success in outbound prospecting and net‑new 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. ~ We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace.

We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible.

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. 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. 116,064 — $174,096 CAD 116,064 — $174,096 CAD #

📌 Account Executive - Diversity and Inclusion Software Sales - REMOTE (Mississauga)
🏢 Block
📍 Mississauga