Mid-Market Account Executive

The Role

At Square, we’re re-imagining how mid-market businesses grow. As an Account Executive on our Mid-Market 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 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

5+ 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)

Expertise closing complex, multi-threaded deals with longer sales cycles

Demonstrated ability in building pipeline from scratch using targeted, strategic outreach

Exceptional communication, presentation, and negotiation skills across phone, video, and written channels

Expertise with 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.

A bias towards adopting the latest technology solutions to advance your selling capacity

BA/BS degree or equivalent experience

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to identity or other legally protected class.

We believe in being fair, and 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 their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page.

Block is a globally distributed company and this role will require working with other employees in multiple time zones. You may be required to perform work outside of normal business as part of this role