Senior Outbound Account Executive — Mid-Market (Remote)

Square; Philadelphia (Philadelphia County); Remote; USD 184,000 - 253,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement plans

Family planning options

Job summary

Square is seeking a Senior Sales Account Executive to drive outbound, full-cycle sales with mid-market merchants. You will own the pipeline from prospecting to close, build multi-product solutions, and collaborate with BD, Marketing, and Product to tailor Square’s ecosystem to each merchant.

The role requires at least 6+ years of closing experience, a BA/BS or equivalent, and a proven track record of hitting targets. Expect a fast-paced environment with strong incentives and remote work options.

Qualifications

• 6+ years of sales experience in a full cycle closing role.
• BA/BS degree or relevant experience.
• Proven track record of exceeding sales targets and closing complex multi-product deals.
• Ability to drive deals independently in a fast-paced environment.
• Business development experience (new logo sourcing).
• Collaborative team player with cross-functional savvy.
• 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 targeted campaigns.
• Develop multi-product solutions across Square's ecosystem for each merchant.
• Partner with Business Development on lead flow while driving net-new logo acquisition.
• Conduct high-impact discovery, demos, and negotiations across multi-stakeholder deals.
• Act as a consultant and trusted advisor across BDR, AE, and AM roles when needed.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations.
• Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
• Consistently hit and exceed monthly and quarterly revenue goals.

Skills

Full cycle sales

Sales experience

Deal closing

Prospecting

Collaborative

Salesforce experience

Education

BA/BS degree or equivalent experience

Tools

Salesforce

Job description

Square is seeking a Senior Sales Account Executive to drive outbound, full-cycle sales with mid-market merchants. You will own the pipeline from prospecting to close, build multi-product solutions, and collaborate with BD, Marketing, and Product to tailor Square’s ecosystem to each merchant.

The role requires at least 6+ years of closing experience, a BA/BS or equivalent, and a proven track record of hitting targets. Expect a fast-paced environment with strong incentives and remote work options.