Mid-Market Account Executive

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same. The Role At Square, we’re re-imagining how mid-market businesses grow. As a Senior Sales Account Executive on our 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. 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 5+ years of sales experience in a full cycle closing role A BA/BS degree or relevant experience Demonstrated exceeding sales targets, selling a diverse ecosystem of products, and closing complex deals The ability to drive deals independently in a fast-paced, dynamic environment Business development experience (e.g. new logo sourcing and acquisition) A collaborative and team player mentality Prior Salesforce experience or equivalent 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