Senior Outbound AE - Mid‑Market, Multi‑Product Deals

Square; Chicago (IL); On-site; USD 145,000 - 217,000; Full time

Benefits offered by this job

Health insurance

401(k)

Job summary

Square is seeking a Senior Sales Account Executive for its Outbound Team. You will own the full outbound sales cycle—from prospecting to close—building a high-quality pipeline and assembling multi-product solutions for mid-market merchants.

You will run sophisticated, multi‑product deals from first touch to final close, blending hunter instincts with consultative depth and strategic execution. This role favors an experienced closer who thrives in outbound environments and targets ambitious

Qualifications

• 4+ years of sales experience in a full cycle closing role.
• 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 (e.g. new logo sourcing and acquisition).
• A collaborative and team player mentality.
• Prior Salesforce experience or equivalent.

Responsibilities

• Own the full outbound sales cycle from prospecting to close with mid-market merchants.
• Build and manage a high-quality pipeline through cold outreach and campaigns.
• Develop multi-product solutions across Square’s ecosystem tailored to each merchant.
• Partner with Business Development on lead flow and independently drive net-new logos.
• Conduct high-impact discovery, demos, and negotiations with multi-stakeholder deals.
• Act as a consultant and trusted adviser across BDR, AE, and AM responsibilities when needed.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations.
• Maintain disciplined pipeline management and forecasting in Salesforce.
• Consistently hit and exceed revenue goals monthly and quarterly.

Skills

Full-cycle sales

Outbound prospecting

Deal closing

Salesforce CRM

Team collaboration

Education

BA/BS degree or relevant experience

Tools

Salesforce

Job description

Square is seeking a Senior Sales Account Executive for its Outbound Team. You will own the full outbound sales cycle—from prospecting to close—building a high-quality pipeline and assembling multi-product solutions for mid-market merchants.

You will run sophisticated, multi‑product deals from first touch to final close, blending hunter instincts with consultative depth and strategic execution. This role favors an experienced closer who thrives in outbound environments and targets ambitious