Mid Market Account Executive

Role Overview

As a Mid Market Account Executive on the Outbound Team, you’ll bring Square’s ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You’ll run sophisticated, multi-product deals from the first touch to final close — blending hunter instincts, consultative depth, and strategic execution.

What You Will Do

Own the full outbound sales cycle — from prospecting to negotiation to close — with SMB and mid-market merchants. Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.

Why It Might Be a Fit

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.

Requirements

• 4+ years of full-cycle B2B sales experience with consistent quota achievement
• Proven success in outbound prospecting and net-new business creation (SaaS or fintech preferred)
• Experience closing complex, multi-threaded deals with longer sales cycles
• Ability to build pipeline from scratch using targeted, strategic outreach
• Exceptional communication, presentation, and negotiation skills across phone, video, and written channels
• Strong consultative selling skills — diagnose business challenges and map tailored solutions
• A hunter’s mindset — resilient, creative, and driven to win
• Ability to work independently while contributing to a team-first environment
• Advanced proficiency with Salesforce and modern sales tools
• BA/BS degree or equivalent experience

Benefits

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning