Senior Outbound Sales Executive - Mid-Market, Multi-Product

Square; Portland (OR); On-site; USD 164,000 - 297,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Family planning support

Job summary

Square is seeking a Senior Sales 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 build a high-quality pipeline through cold outreach, social selling, and targeted campaigns.

In this role you will develop multi-product solutions across Square’s ecosystem, collaborate with Business Development, and act as a trusted advisor to merchants.

Qualifications

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

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 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 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.

Skills

Full cycle sales

Negotiation

Prospecting

Collaborative

Sales strategy

Education

BA/BS degree

Tools

Salesforce

Job description

Square is seeking a Senior Sales 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 build a high-quality pipeline through cold outreach, social selling, and targeted campaigns.

In this role you will develop multi-product solutions across Square’s ecosystem, collaborate with Business Development, and act as a trusted advisor to merchants.