Key skills
B2B SalesOutbound ProspectingNet-new Business CreationSaaSFintechComplex Deal ClosingPipeline BuildingSalesforceSales ToolsConsultative SellingResilienceIndependenceCommunicationNegotiationSales
About this role
Square is a company that provides integrated, omnichannel solutions to help sellers grow their businesses. The Senior Sales Account Executive will own the outbound sales cycle, building and managing a pipeline while delivering tailored solutions to small and midsize businesses.
Responsibilities:
- 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
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