Senior Outbound AE - Mid-Market & Multi-Product Deals

Square; Boston (MA); Remote; USD 150,000 - 230,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Competitive compensation

Paid time off

Job summary

Square is seeking a Senior Sales Account Executive for our Outbound Team to bring Square’s ecosystem to new mid-market sellers. You’ll build, shape, and close multi-product deals from first touch to close, blending hunter instincts with consultative depth and strategic execution.

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

Qualifications

• 3+ years of sales experience in a full cycle closing role.
• A BA/BS degree or relevant experience.
• History of exceeding sales targets and closing complex deals.
• Ability to drive deals independently in a fast-paced environment.
• Business development experience with new logo sourcing.
• Collaborative, team-oriented mindset.
• 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 new logos.
• Conduct discovery, demos, and negotiations with multi-stakeholder buyers.
• Act as a consultant across BDR, AE, and AM duties when needed.
• Collaborate with Product, Marketing, Implementation, and Operations.
• Maintain disciplined pipeline management and forecasting in Salesforce.
• Consistently hit and exceed monthly and quarterly revenue targets.

Skills

Full cycle sales

Outbound sales

Mid-market deals

Salesforce

Negotiation

BD experience

Team player

Education

BA/BS degree

Job description

Square is seeking a Senior Sales Account Executive for our Outbound Team to bring Square’s ecosystem to new mid-market sellers. You’ll build, shape, and close multi-product deals from first touch to close, blending hunter instincts with consultative depth and strategic execution.

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