Mid-Market Account Executive, Remote

Kansas City, MO · US - CA - San Francisco City - Remote · USD 129,600-194,400 · 5+ years experience · Remote · Posted Sep 23, 2026

At a glance

As a Senior Sales Account Executive on the Outbound Team at Square, you will bring Square's ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline.
You will run sophisticated, multi-product deals from the first touch to final close while blending hunter instincts, consultative depth, and strategic execution.

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 on a monthly and quarterly basis.

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 such as new logo sourcing and acquisition.
A collaborative and team player mentality.
Prior Salesforce experience or equivalent.