Senior Sales Account Executive

Owns the full outbound sales cycle for SMB and mid-market merchants, building pipeline, selling Square’s multi-product ecosystem, and closing complex deals. The role requires at least three years of full-cycle B2B sales experience, strong consultative selling skills, and Salesforce proficiency.

About the job

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 needs.
Partner with Business Development on lead flow while independently driving net-new logo acquisition.
Conduct discovery, demos, and negotiations across multi-stakeholder deals.
Act as a consultant and trusted advisor, flexing across BDR, AE, and AM responsibilities when needed.
Collaborate cross-functionally with Product, Marketing, Implementation, and Operations.
Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
Consistently hit and exceed monthly and quarterly revenue goals.

Requirements

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 experience 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, including diagnosing business challenges and mapping tailored solutions.
Resilient, creative, and driven approach to sales.
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.