Senior Outbound Sales Account Executive

The Role At Square, we’re re-imagining how small and midsize 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 SMB and 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 3+ 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 . Pay Transparency Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future. To find a location's zone designation, please refer to this resource. Zone A: ($156,200 - $234,200) Zone B: ($145,200 - $217,800) Zone C: ($137,400 - $206,200) Zone D: ($129,600 - $194,400) Amounts listed above include target variable compensation. Equal Opportunity Employment Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. We believe in being fair, and we are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with our recruiter, who will treat these requests as confidentially as possible. #J-18808-Ljbffr Centaur Labs