Senior Outbound AE - Mid-Market Growth

Square; New York (NY); Remote; USD 156,000 - 234,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement plans

Job summary

Square is seeking a Senior Sales Account Executive to drive outbound growth for mid-market merchants. You will own the entire sales cycle, build a strong pipeline, and tailor multi-product solutions from Square’s ecosystem to each merchant’s needs.

You’ll close high‑stakes deals, partner with Business Development for new logos, and collaborate with Product, Marketing, and Implementation to deliver cohesive solutions. Remote-friendly environment with clear growth paths.

Qualifications

• 5+ years of sales experience in a full cycle closing role.
• BA/BS degree or relevant experience.
• Demonstrated exceeding sales targets and closing complex deals.
• Ability to drive deals independently in a fast-paced environment.
• Business development experience (new logo sourcing)
• Collaborative and team player mentality.
• Prior Salesforce experience or equivalent.

Responsibilities

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

Skills

Sales experience

Full-cycle closing

Team collaboration

Target achievement

Sales strategy

Education

BA/BS degree

Tools

Salesforce

Job description

Square is seeking a Senior Sales Account Executive to drive outbound growth for mid-market merchants. You will own the entire sales cycle, build a strong pipeline, and tailor multi-product solutions from Square’s ecosystem to each merchant’s needs.

You’ll close high‑stakes deals, partner with Business Development for new logos, and collaborate with Product, Marketing, and Implementation to deliver cohesive solutions. Remote-friendly environment with clear growth paths.