Sales Manager, Small & Medium Business

Block•Chicago, IL

5d•Remote

About The Position

Square is building one of the most dynamic inside sales organizations in fintech — and we're looking for a proven Inside Sales Manager to lead, scale, and inspire a remote team of Account Executives. You'll run a high-velocity sales motion where inbound demand meets outbound hustle. Your team will turn thousands of interested sellers into thriving Square customers — and you'll help them do it faster, smarter, and better every quarter. This is a hands-on leadership role for someone who loves building process, coaching talent, and pushing results. You'll lead with data, empower with trust, and create a culture that celebrates performance, grit, and growth. If you're the kind of leader who rolls up your sleeves, drives revenue at scale, and knows how to build a world-class inside sales engine — this is your next big challenge.

Requirements

3–5+ years of inside sales management experience, leading quota-carrying Account Executives
Track record of exceeding team revenue goals in a high-velocity sales environment
Proven success hiring, ramping, and developing AEs to full productivity
Experience managing remote teams with a focus on metrics and accountability
Strong business acumen with ability to build scalable systems and processes
Exceptional communication and influencing skills across all levels
Data-driven approach to coaching and performance management
Experience in fintech, payments, or SaaS sales management
Familiarity with Salesforce, Gong, and modern sales engagement tools (e.g., Outreach, Salesloft)
Background leading teams selling into SMBs across multiple verticals

Responsibilities

Lead and develop a high-performing remote team of Account Executives focused on full-cycle selling
Drive predictable revenue growth through clear KPIs, metrics, and consistent quota achievement
Hire, train, and promote top talent while building a culture of continuous improvement
Coach for excellence through live call participation, 1:1s, and data-backed feedback
Create scalable processes to optimize pipeline management and forecasting accuracy
Partner with Marketing, Product, and Sales Ops to strengthen our go-to-market motion
Use data-driven insights to track performance and implement strategic improvements

Benefits

Healthcare coverage (Medical, Vision and Dental insurance)
Health Savings Account and Flexible Spending Account
Retirement Plans including company match
Employee Stock Purchase Program
Wellness programs, including access to mental health, 1:1 financial planners, and a monthly wellness allowance
Paid parental and caregiving leave
Paid time off (including 12 paid holidays)
Paid sick leave (1 hour per 26 hours worked (max 80 hours per calendar year to the extent legally permissible) for non-exempt employees and covered by our Flexible Time Off policy for exempt employees)
Learning and Development resources
Paid Life insurance, AD&D, and disability benefits