Senior Mid-Market AE: Remote, Outbound & Multi-Product Deals

Square; Washington (District of Columbia); Remote; USD 184,000 - 253,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Modern family planning

Job summary

Square is hiring a Senior Sales Account Executive for its Outbound Team. You will own the full outbound sales cycle with mid-market merchants, building a strong pipeline and developing multi-product solutions across Square’s ecosystem.

You’ll partner with BD on lead flow, conduct discovery and demos, and close complex multi-product deals while acting as a trusted advisor across BDR, AE, and AM roles. If you excel in outbound environments, thrive on solving meaningful business challenges, and

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.
• Experience in business development (new logo sourcing).
• Collaborative team player mentality.
• 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, social selling, and targeted campaigns.
• Develop multi-product solutions across Square's ecosystem tailored to each merchant.
• Partner with Business Development on lead flow while driving net-new logo acquisition.
• Conduct discovery, demos, and negotiations with multi-stakeholder deals.
• Act as a consultant and trusted advisor across BDR, AE, and AM roles as needed.
• Collaborate with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.
• Maintain pipeline management and forecasting accuracy in Salesforce.
• Consistently hit and exceed revenue goals monthly and quarterly.

Skills

Full-cycle sales

BD / new logo sourcing

Outbound selling

Multi-product solutions

Negotiation

Sales forecasting

Education

BA/BS or equivalent

Tools

Salesforce

Job description

Square is hiring a Senior Sales Account Executive for its Outbound Team. You will own the full outbound sales cycle with mid-market merchants, building a strong pipeline and developing multi-product solutions across Square’s ecosystem.

You’ll partner with BD on lead flow, conduct discovery and demos, and close complex multi-product deals while acting as a trusted advisor across BDR, AE, and AM roles. If you excel in outbound environments, thrive on solving meaningful business challenges, and