Senior Mid-Market SaaS Sales Executive

Square; Pittsburgh (Allegheny County); On-site; USD 110,000 - 165,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Family planning

Job summary

Square is seeking a Senior Sales Account Executive to spearhead outbound growth for mid-market merchants across diverse industries. You will own the full cycle from prospecting to close, building a robust pipeline and delivering multi-product solutions tailored to each merchant’s needs.

You will collaborate with Business Development, Product, and Marketing to close complex deals, acting as a trusted advisor and ensuring accurate forecasting in Salesforce while aiming to meet ambitious revenue

Qualifications

• 5+ years of full-cycle B2B sales experience with quota achievement.
• Proven success in outbound prospecting and net-new business creation (SaaS or fintech).
• Experience closing complex, multi-threaded deals with longer sales cycles.
• Ability to build pipeline from scratch using targeted, strategic outreach.
• Excellent communication, presentation, and negotiation skills.
• Strong consultative selling skills to map tailored solutions.
• Hunter mindset with resilience and drive to win.
• Able to work independently while contributing to a team.
• Advanced proficiency with Salesforce.
• BA/BS degree or equivalent experience.

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 net-new logo acquisition.
• Conduct high-impact discovery, demos, and negotiations with multi-stakeholder deals.
• Act as a consultant and trusted advisor across BDR, AE, and AM responsibilities.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations.
• Maintain disciplined pipeline management and forecasting in Salesforce.
• Consistently hit and exceed revenue goals — monthly and quarterly.

Skills

B2B sales

Outbound prospecting

Closing complex deals

Pipeline development

Communication

Negotiation

Consultative selling

Hunter mindset

Independent work

Salesforce

Education

BA/BS degree or equivalent experience

Tools

Salesforce

Job description

Square is seeking a Senior Sales Account Executive to spearhead outbound growth for mid-market merchants across diverse industries. You will own the full cycle from prospecting to close, building a robust pipeline and delivering multi-product solutions tailored to each merchant’s needs.

You will collaborate with Business Development, Product, and Marketing to close complex deals, acting as a trusted advisor and ensuring accurate forecasting in Salesforce while aiming to meet ambitious revenue