Senior Mid-Market Account Executive

The Role

At Square, we’re re-imagining how mid-market businesses grow. As a Senior Mid-Market Account Executive on our Mid-Market 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.

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.

You Will

• Own the full outbound sales cycle — from prospecting to negotiation to close — with mid-market merchants.
• Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.
• Develop multi-product solutions across Square’s ecosystem and tailor them to each merchant’s unique needs.
• Partner with Business Development on lead flow while independently driving net-new logo acquisition.
• Conduct high-impact discovery, demos, and negotiations with decisiveness across multi-stakeholder deals.
• Act as a consultant and trusted advisor — seamlessly flexing across BDR, AE, and AM responsibilities when needed.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.
• Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
• Consistently hit and exceed revenue goals — monthly and quarterly.

You Have

• 7+ 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), specifically within a target-account motion.
• Experience closing complex, multi-threaded deals with longer sales cycles.
• Ability to build a 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.
• A bias towards adopt