Senior Mid-Market Account Executive

<h4><strong>The Role</strong></h4> <p>At Square, we’re re-imagining how mid-market businesses grow. As a <strong>Senior</strong><strong> Mid-Market Account Executive</strong> 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.</p> <p>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.</p> <h4><strong>You Will</strong></h4> <ul> <li><strong>Own the full outbound sales cycle</strong> — from prospecting to negotiation to close — with mid-market merchants.</li> <li><strong>Build and manage a high-quality pipeline</strong> through cold outreach, social selling, targeted campaigns, and creative outbound strategies.</li> <li><strong>Develop multi-product solutions</strong> across Square’s ecosystem and tailor them to each merchant’s unique needs.</li> <li><strong>Partner with Business Development</strong> on lead flow while independently driving net-new logo acquisition.</li> <li><strong>Conduct high-impact discovery, demos, and negotiations</strong> with decisiveness across multi-stakeholder deals.</li> <li><strong>Act as a consultant and trusted advisor</strong> — seamlessly flexing across BDR, AE, and AM responsibilities when needed.</li> <li><strong>Collaborate cross-functionally</strong> with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.</li> <li><strong>Maintain disciplined pipeline management</strong> and forecasting accuracy in Salesforce.</li> <li><strong>Consistently hit and exceed revenue goals</strong> — monthly and quarterly.<br><br></li> </ul> <h4><strong>You Have</strong></h4> <ul> <li><strong>7+ years</strong><strong> of full-cycle B2B sales experience</strong> with consistent quota achievement.</li> <li><strong>Proven success in outbound prospecting</strong> and net-new business creation (SaaS or fintech preferred), specifically within a target-account motion.</li> <li><strong>Experience closing complex, multi-threaded deals</strong> with longer sales cycles.</li> <li><strong>Ability to build a pipeline from scratch</strong> using targeted, strategic outreach.</li> <li><strong>Exceptional communication, presentation, and negotiation skills</strong> across phone, video, and written channels.</li> <li><strong>Strong consultative selling skills</strong> — diagnose business challenges and map tailored solutions.</li> <li><strong>A hunter’s mindset</strong> — resilient, creative, and driven to win.</li> <li><strong>Ability to work independently</strong> while contributing to a team-first environment.</li> <li><strong>Advanced proficiency with Salesforce</strong> and modern sales tools.</li> <li><strong>A bias towards adopting the latest technology solutions</strong> to advance your selling capacity</li> <li><strong>BA/BS degree or equivalent experience</strong>.</li> </ul> <p>We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is a proud