# Mid-Market Account Manager

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Chicago, IL
**Role:** Account Management
**Salary:** $41 – $78/hr
**Experience:** 5+ years
**Skills:** Account Management, SaaS Sales, Payments Technology, Pos Systems, Consultative Selling, Contract Negotiation, Cross-Selling, Customer Retention, Technical Solutioning, Stakeholder Management
**Posted:** 2026-06-08

> Drive growth and retention for ~175 mid-market retail accounts at Square by consulting on payments, business management, and banking tools while expanding use cases and negotiating contracts.

## Job Description

## You Will
- Own and maintain relationships across a portfolio of ~175 mid-market retail sellers, driving account expansion, retention, and satisfaction
- Consult with business owners and operators to uncover opportunities across payments, business management, and banking tools
- Retain and grow portfolio through use-case expansion, cross-sell opportunities, and customized seller onboarding experiences
- Identify opportunities for technical Square solutions to address existing customer needs; project manage execution in collaboration with cross-functional teams
- Act as the voice of the customer, advocating for mid-market seller needs with Product, Engineering, and Operations teams
- Negotiate contracts for use-case expansion and retention of your sellers
- Deliver white-glove client service, ensuring resolution of seller issues
- Inform operations and program design for this segment at scale

## You Have
- 5+ years of experience in account management or sales, ideally within SaaS, payments, or POS technology
- Proven success growing and retaining a book of business
- Consistent over-performance on key metrics and revenue targets
- Strong discovery and consultative selling skills
- Experience in the retail industry preferred, but not required
- Technical solutioning skills, including requirements gathering and translating customer needs into scalable solutions
- Demonstrated success retaining and expanding strategic accounts
- Experience negotiating contracts and pricing with senior stakeholders
- Exceptional written and verbal communication skills
- Creative, strategic problem-solver who thrives in ambiguous environments
- Growth mindset, empathetic collaborator, and positive team player

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