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About the Role
At Square, we’re re-imagining how mid-market businesses grow. As a Mid-Market Account Executive, 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.
Responsibilities
- 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.
Requirements
- 3+ 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.
Skills
- Salesforce
- Consultative selling
- Outbound prospecting
- Negotiation
- Presentation
- Communication
Experience Level
- 3+ years
Education Level
- BA/BS degree or equivalent experience
Salary/Compensations
- $152,320 - $228,480 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
- 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.