Head of Retail Sales (Chicago)

Brick Executive Search has been exclusively retained to search for an elite , high level Head of Sales for a fast pace sales team serving a very fast paced Retailer.

The Position

Head of Retail Sales

Location

Corporate Headquarters in Chicago with 50-75% travel to 40 stores

Overview

Take charge of skyrocketing sales and building strong customer relationships across the company's 40 stores. Lead our Stylists to crush sales goals by setting clear metrics (like client outreach through Endear), delivering top-notch training, managing client books, and using StoreForce to track performance in our fast-fashion world with over 60,000 SKUs. Work closely with regional managers to drive revenue, spark customer loyalty, and keep our stores buzzing with energy.

Key Responsibilities

• Sales Performance & Strategy: Create bold sales plans to boost revenue; set high-impact targets for Stylists (like conversion rates and transaction values); track progress and adjust tactics to consistently surpass goals.
• Clienteling Metrics & Execution: Set and enforce clear metrics (e.g., 3+ client calls/day via Endear); monitor client book growth and engagement to drive repeat business and personalized sales.
• Stylist Training & Motivation: Build and lead dynamic training programs on sales techniques, client relationships, and fast-fashion trends; provide hands-on coaching and incentives to create a fired-up, competitive sales team.
• Technology Utilization: Use Endear to track client outreach and StoreForce for real-time sales insights; streamline reporting and make data-driven decisions to fuel growth.
• Travel & Field Support: Hit the road (50-75% travel) to check on sales performance, coach Stylists, fix gaps, and roll out initiatives that drive immediate revenue.
• Customer Loyalty & Retention: Lead efforts to create personalized client experiences; promote new arrivals (60k+ SKUs) to keep customers coming back and build long-term loyalty.
• Team Leadership: Hire, develop, and inspire top Stylist talent; partner with regional managers to align on goals; coach up underperformers and celebrate top performers.
• Cross-Functional Collaboration: Team up with merchandising, marketing, and operations to ensure product availability, promotions, and strategies align for seamless sales execution.
• Financial Analysis & Forecasting: Dive into sales data, predict trends, manage P&L components, and fine-tune pricing/promotions to boost profitability and stay competitive.
• Market & Competitor Insights: Keep an eye on industry trends, competitors, and customer behaviors to spot sales opportunities and adjust strategies for ongoing growth.

Qualifications

• Experience: 8+ years leading retail sales, ideally in fast fashion or apparel; proven success in driving revenue, clienteling, and managing multi-store teams in high-SKU environments.
• Skills: Master of sales strategy, client management, data analytics, and team motivation; skilled with retail tech (e.g., Endear, StoreForce, CRM); strong at negotiating, presenting, and coaching.
• Education: Bachelor's in Business, Marketing, Retail Management, or related field; MBA preferred.
• Other: Ready for frequent travel; driven to exceed targets; thrives in a fast-paced, high-energy setting; deep understanding of fast-fashion trends and what drives sales.