Retail Success Manager: LEAP (Multi-Brand)

Leap • Chicago, IL

23h • Hybrid

About The Position

This is an opportunity to own a portfolio of brands and stores end-to-end, driving performance, deepening partnerships, and developing the people who make it all work. As a Retail Success Manager, you'll be the connective tissue between Leap's operations and the brand executives who trust us with their physical retail presence. You'll toggle between coaching a Store Manager on the floor on a Tuesday and leading a strategic brand review with a founder on Wednesday. You'll know the P&L as well as you know your team. Leap believes the future of retail is omnichannel and the next generation of brands belong in neighborhoods, not just on screens. The Leap platform powers retail across over 100 stores for 50 brands with ambitions of scaling to thousands of stores and hundreds of brands. While our platform provides the data and infrastructure across our 100+ stores, our people are the key to our success. We are looking for smart, energized individuals who are ready to act as owners and help us build our platform.

Requirements

• Based in Chicago; hybrid role with a minimum of 3 in-store days per week
• 6+ years of progressive retail leadership experience, with 2+ years in multi-unit management across a minimum of 5 locations
• Demonstrated success leading remote, multi-store teams to drive client experience, operational excellence, and business performance
• Strong relationship-building skills across internal teams, store staff, and brand partners
• Ability to travel regularly within NYC and up to twice annually out of state
• Must be 18+ years of age
• Comfortable with active, on-floor responsibilities, including extended standing/walking and lifting up to 50 lbs or using ladders as needed

Responsibilities

• Run performance across a portfolio of brands and stores; analyzing data, identifying gaps, and building actionable plans that consistently hit sales, remittance, and profitability targets.
• Coach and develop Store Managers with a focus on sales, customer experience, and retention.
• Own the full talent pipeline: recruiting, hiring, onboarding, and ongoing development.
• Serve as the primary relationship owner for brand executives, translating performance data into insights, aligning on strategy, and leading renewal and expansion conversations alongside the Growth team.
• Align internal teams (marketing, merchandising, finance, operations) around what brands need and what stores are seeing.
• Be the voice that connects the floor to the boardroom.

Benefits

• Unlimited PTO (blackout periods apply)
• Bonus Eligible
• Healthcare benefits (medical, dental, vision)
• Flexible time off (paid company holidays, unlimited paid time off, sick leave, parental leave)
• Access to company perks (commuter benefits, 401K, paid sabbatical, employee discounts at Leap stores, employee referral bonus, telecom reimbursement)
• Employee Assistance Program
• Employee discount + wardrobe allotment for participating Leap brands

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed