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SquareSquare

Mid-Market Sales Manager

Leads and develops a team of Account Executives selling complex, multi-stakeholder deals in the mid-market segment. The role emphasizes hiring, coaching, pipeline and forecast discipline, co-selling, and cross-functional commercial execution.

About the job

Responsibilities

Build a High-Performance Team

  • Hire Account Executives who can run complex, multi-stakeholder deals and raise the bar with every addition to the team.
  • Develop a culture of ownership, accountability, continuous learning, and high standards.
  • Identify future top performers early and create development plans that accelerate their growth.

Co-Sell on Complex Deals

  • Sell alongside the team in discovery, business case development, and negotiation on important pursuits.
  • Engage senior stakeholders, including owners, operations, and finance, and help the team multi-thread rather than sell to a single champion.
  • Apply commercial judgment to pricing, deal structure, and competitive displacement.
  • Advance deals while developing Account Executives' ability to run future opportunities independently.

Coach Through Data and Business Intelligence

  • Lead through rigorous pipeline inspection, forecasting, and performance diagnostics.
  • Use leading indicators to identify performance gaps early and coach representatives toward sustainable improvement.
  • Turn data into action by identifying trends, diagnosing root causes, and driving measurable improvements.
  • Forecast accurately on long-cycle deals through disciplined stage integrity.

Drive Operational Excellence

  • Establish predictable operating rhythms around forecasting, pipeline management, and business reviews.
  • Build disciplined execution that creates consistent, repeatable revenue outcomes.
  • Improve sales processes, simplify execution, and eliminate friction.
  • Build repeatable plays for winning the segment, including implementation and expansion.

Lead Through Influence

  • Partner with Sales Leadership, Marketing, Enablement, Operations, Partnerships, and Product to improve the customer journey and strengthen commercial execution.
  • Use customer insights and field intelligence to shape strategy and influence product evolution.
  • Lead through change while maintaining high performance.

Requirements

  • 6+ years of experience as a sales manager, including experience leading teams selling into complex, multi-stakeholder accounts with sales cycles measured in months.
  • Experience hiring, ramping, and retaining Account Executives who can run considered, competitive deals.
  • Experience developing strong performers into people who win larger and more complex deals.
  • Proven ability to collaborate across teams and inspire change.
  • Leadership and coaching experience, with a desire to help others perform at their best.
  • Expertise in creating structure around sales metrics and managing yourself and others to achieve them, including forecast accuracy on long-cycle deals.
  • Ability to refine decision-making and consider the downstream and upstream effects of potential decisions.

Compensation and Benefits

  • Remote work.
  • Medical insurance.
  • Flexible time off.
  • Retirement savings plans.
  • Modern family planning benefits.

Skills

Sales Management, Account Executive Coaching, Pipeline Management, Sales Forecasting, Sales Metrics, Business Intelligence, Complex Sales, Multi-Stakeholder Selling, Deal Negotiation, Pricing Strategy, Competitive Displacement, Performance Diagnostics, Cross-Functional Collaboration, Sales Enablement, CRM

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