# Mid-Market Sales Manager

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Remote
**Role:** Account Management
**Experience:** 6+ years
**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
**Posted:** 2026-08-07

> 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.

## Job Description

## 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.

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