Drimva

Block

Mid-Market Account Executive

$130K–$234K

Chicago, IL, United States of America +1 · Remote · Full-time · Posted Sep 25, 2026

Location
Chicago, IL, United States of America
US - CA - SoCal - Remote
Experience
4+ years of sales experience in a full cycle closing role.
Education
A BA/BS degree or relevant experience

About the job

Owns outbound sales and closes multi-product deals with mid-market merchants, from prospecting through negotiation and close.

What you'll do

  • Build and manage an outbound pipeline, acquire new merchant accounts, and meet revenue goals.
  • Discover merchant needs and tailor Square ecosystem solutions; conduct demos and negotiate complex, multi-stakeholder deals.
  • Manage pipeline and forecasts in Salesforce and collaborate with Business Development and cross-functional teams.

What they ask for

  • 4+ years of sales experience in a full cycle closing role.
  • Demonstrated success exceeding sales targets, selling a diverse product ecosystem, and closing complex deals.
  • Ability to drive deals independently in a fast-paced environment; business development experience in new-logo sourcing and acquisition.
  • Prior Salesforce experience or equivalent.

Nice to have

Pay

Zone A: ($156,200 - $234,200) USD total pay; Zone B: ($145,200 - $217,800) USD total pay; Zone C: ($137,400 - $206,200) USD total pay; Zone D: ($129,600 - $194,400) USD total pay

Tools

Salesforce

AI focus

The employer may use automated AI tools to evaluate job applications for efficiency and consistency.

Model-written summary · the original posting is authoritative

First seen Oct 10, 2026 · Last verified Nov 5, 2026 (UTC)