Remote Enterprise Account Executive for High-Value Deals

Square

Chicago (IL)

On-site

USD 263,000 - 395,000

Full time

14 days+

A complete application in a minute

Tailored resume and cover letter, ready to send.

Get past ATS filters

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Job summary

Square is seeking an Enterprise Account Executive to lead the most strategic, high-value deals and own the full lifecycle from initial outreach to signed contracts. You will navigate multi-threaded cycles with executive stakeholders, work closely with Solutions Engineering on API integrations, and build compelling business cases to demonstrate ROI.

You will mentor and align cross-functional teams, influence product roadmaps, and represent Square at C-suite meetings and industry events while

Qualifications

8+ years of enterprise sales experience and end-to-end deal ownership.
Fluency in conversations involving API integrations and platform configuration.
Proven ability to orchestrate multi-stakeholder deals with cross-functional teams.
Executive presence for C-suite meetings and stage presentations.

Responsibilities

Craft and Lead Deal Strategy tailored to client priorities and ROI.
Own the full sales cycle from prospecting to close with precision.
Lead complex technical sales cycles in partnership with Solutions Engineering.
Coordinate cross-functional alignment across Finance, Legal, Risk, Product, and Sales.
Represent Square at high-level meetings and industry events.