Senior Account Executive, Mid-Market

Square; Toronto; Remote; CAD 116,000 - 174,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Family planning benefits

Job summary

Square is hiring a Senior Sales Account Executive for the Mid‑Market Team in Canada. You will own the full outbound sales cycle, build a high-quality pipeline, and develop multi‑product solutions across Square’s ecosystem for mid‑market merchants.

You will partner with Business Development, conduct discovery, demos, and negotiations, and act as a trusted advisor across BDR, AE, and AM roles while collaborating with Product, Marketing, Implementation, and Operations.

Qualifications

• 5+ years of full-cycle B2B sales experience.
• Proven success in outbound prospecting and net-new business.
• Experience closing complex, multi-threaded deals.
• Ability to build pipeline from scratch using targeted outreach.
• Exceptional communication, presentation, and negotiation skills across phone, video, and written channels.
• Strong consultative selling skills — diagnose business challenges and map tailored solutions.
• Hunter’s mindset — resilient, creative, and driven to win.
• Ability to work independently while contributing to a team.
• Advanced proficiency with Salesforce and modern sales tools.
• BA/BS degree or equivalent experience.

Responsibilities

• Own the full outbound sales cycle—from prospecting to negotiation to close—for mid-market merchants.
• Build and manage a high-quality pipeline through cold outreach and targeted campaigns.
• Develop multi-product solutions across Square’s ecosystem tailored to each merchant.
• Partner with Business Development on lead flow while independently driving net-new logo acquisition.
• Conduct high-impact discovery, demos and negotiations with multi-stakeholder teams.
• Act as a consultant and trusted advisor across BDR, AE, and AM responsibilities when needed.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations.
• Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
• Consistently hit and exceed revenue goals—monthly and quarterly.

Skills

Full-cycle B2B sales

Outbound Prospecting

Multi-thread Deals

Pipeline Management

Negotiation Skills

Consultative Selling

Hunter Mindset

Independent Work

Salesforce Pro

BA/BS Degree

Education

BA/BS degree or equivalent

Tools

Salesforce

Job description

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. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale. Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

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. You’ll run sophisticated, multi‑product deals from the first touch to final close — blending hunter instincts, consultative depth, and strategic execution.

If you’re an experienced closer who thrives in outbound environments, loves solving meaningful business challenges, and consistently delivers against ambitious targets — this is your role.

You Will

• 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.
• Develop multi‑product solutions across Square’s ecosystem and tailor them to each merchant’s unique needs.
• Partner with Business Development on lead flow while independently driving net‑new logo acquisition.
• Conduct high‑impact discovery, demos, and negotiations with decisiveness across multi‑stakeholder deals.
• Act as a consultant and trusted advisor — seamlessly flexing across BDR, AE, and AM responsibilities when needed.
• Collaborate cross‑functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.
• Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
• Consistently hit and exceed revenue goals — monthly and quarterly.

You Have

• 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.
• Strong consultative selling skills — diagnose business challenges and map tailored solutions.
• A hunter’s mindset — resilient, creative, and driven to win.
• Ability to work independently while contributing to a team‑first environment.
• Advanced proficiency with Salesforce and modern sales tools.
• BA/BS degree or equivalent experience

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. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances.

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page

Block takes a market-based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two zones based on a cost of labor index for that geographic area. 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.

Zone A: $116,064 — $174,096 CAD

Zone B: $116,064 — $174,096 CAD

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.

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.

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