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About the Role
As an Account Executive on Square's Mid-Market Team, you will bring Square’s ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You will run sophisticated, multi-product deals from the first touch to final close, blending hunter instincts, consultative depth, and strategic execution. This role is ideal for an experienced closer who thrives in outbound environments, loves solving meaningful business challenges, and consistently delivers against ambitious targets.
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
- 6+ 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.
- Requires working with other employees in multiple time zones.
- May be required to perform work outside of normal business hours.
Skills
- Salesforce
- Modern sales tools
- Outbound prospecting
- Net-new business creation
- Closing complex deals
- Consultative selling
- Communication
- Presentation
- Negotiation
Location
- Globally distributed
Work Type
- Remote
Experience Level
- 6+ years of full-cycle B2B sales experience
Education Level
- BA/BS degree or equivalent experience
Benefits
- Remote work
- Medical insurance
- Flexible time off
- Retirement savings plans
- Modern family planning
About the Company
- Square enables anyone to take payments and never miss a sale, expanding into software to build integrated, omnichannel solutions.
- Square offers solutions for sellers to sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff.
- Square has embedded financial services tools at the point of sale, allowing merchants to access business loans and manage cash flow.
- Afterpay furthers Square's goal to provide omnichannel tools that unlock meaningful value and growth for sellers.
- Square is a partner to sellers of all sizes, from large enterprise-scale businesses to those just starting.
- Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy.
- 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, Block's brands are helping build a financial system that is open to everyone.
Equal Opportunity
- Block is a proud equal opportunity employer.
- We work hard to evaluate all employees and job applicants consistently, without regard to identity or other legally protected class.
- 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.