Elite Mid-Market Outbound Account Executive

Square; San Francisco (CA); Hybrid; USD 198,000 - 297,000; Full time

Benefits offered by this job

Medical insurance

Remote work

Flexible time off

Retirement savings plan

Job summary

Square is seeking a Mid-Market Account Executive on our Outbound Team to bring Square’s ecosystem to new merchants across diverse industries. You’ll own the full outbound sales cycle from prospecting to close, and you’ll build multi-product solutions tailored to each merchant’s needs.

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

Qualifications

• 6+ years of full-cycle B2B sales experience with quota attainment.
• Proven success in outbound prospecting and net-new business creation (SaaS or fintech preferred).
• Experience closing complex, multi-threaded deals with longer sales cycles.
• Advanced proficiency with Salesforce and modern sales tools.

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.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.

Skills

Full-cycle B2B sales

Outbound prospecting

Closing multi-threaded deals

Pipeline building

Communication skills

Consultative selling

Independent work

Salesforce proficiency

Education

BA/BS degree or equivalent experience

Tools

Salesforce

CRM software

Job description

Square is seeking a Mid-Market Account Executive on our Outbound Team to bring Square’s ecosystem to new merchants across diverse industries. You’ll own the full outbound sales cycle from prospecting to close, and you’ll build multi-product solutions tailored to each merchant’s needs.

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