Remote Senior Outbound Account Executive - Mid-Market

Square; Chicago (IL); Remote; USD 164,000 - 297,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plan

Family planning

Job summary

Square is seeking a Senior Sales Account Executive to lead the full outbound sales cycle for mid-market merchants, building a high-quality pipeline and closing multi-product deals. You will collaborate with Product, Marketing, and Implementation to tailor Square’s ecosystem to each merchant’s needs.

This role emphasizes consultative selling, independent deal closure, and consistent achievement of revenue targets in a fast-paced environment.

Qualifications

• 5+ years of experience in a full cycle closing role.
• BA/BS degree or relevant experience.
• Demonstrated exceeding sales targets, selling a diverse ecosystem of products, and closing complex deals.

Responsibilities

• Own the full outbound sales cycle from prospecting to close for mid-market merchants.
• Build and manage a high-quality pipeline through cold outreach and campaigns.
• Develop multi-product solutions across Square’s ecosystem for each merchant.
• Partner with Business Development on lead flow and drive new logo acquisition.
• Conduct discovery, demos, and negotiations across multi-stakeholder deals.

Skills

Full-cycle closing

Sales experience

Outbound/BD experience

Salesforce

Team collaboration

Education

BA/BS degree

Tools

Salesforce

Job description

Square is seeking a Senior Sales Account Executive to lead the full outbound sales cycle for mid-market merchants, building a high-quality pipeline and closing multi-product deals. You will collaborate with Product, Marketing, and Implementation to tailor Square’s ecosystem to each merchant’s needs.

This role emphasizes consultative selling, independent deal closure, and consistent achievement of revenue targets in a fast-paced environment.