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Sales Manager, Small & Medium Business

136k – 245kChicago, ILRemote3+ YOE
Summary

Lead a remote team of Account Executives in high-velocity inside sales for SMBs at Square, driving revenue growth, coaching talent, and optimizing processes with data-driven insights. Requires 3-5+ years of sales management experience in fintech or SaaS.

About the role

You Will

  • 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

You Have

  • 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
Skills
SalesforceGongOutreachSalesloftSalesforce CRMPipeline ManagementSales ForecastingData AnalysisRemote Team ManagementFintech Sales
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