Retail Success Manager: LEAP (Multi-Brand)

At Leap, we believe the future of retail is omnichannel and the next generation of brands belong in neighborhoods, not just on screens. Today, 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. So, come take this leap with us and help us rewrite the future of retail.

Location

This is a hybrid role based in Chicago, with a minimum of 3 in-store days per week.

Annual Pay Range

$105,000–$125,000, based on experience

About the Role

This is not a multi-unit manager role with a fancier title. 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.

Why This Role

• Ownership: You'll run a real portfolio: multiple brands, stores, and the teams who make them successful. The results you drive are visible and yours.
• Impact: High-stakes exposure to the most exciting consumer brands in the market, with a seat at the table on strategy and execution.
• Scale: Operate at the intersection of retail operations, brand partnership, and team leadership in one of the fastest-growing companies in the space.
• Growth: A compelling NYC leadership role for those who want to operate at a high level and build something meaningful.

What You'll Do

• Run the Portfolio Own performance across a portfolio of brands and stores; analyzing data, identifying gaps, and building actionable plans that consistently hit sales, remittance, and profitability targets.
• Develop the Team 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.
• Drive Brand Success 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.
• Operate Cross-Functionally 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.

• Store-level financial, operational, and experience KPIs consistently achieved across your portfolio
• High employee retention, engagement, and a healthy hiring pipeline
• Strong Brand NPS. Brand partners renew, expand, and advocate for Leap
• You're the person brands and internal teams trust to get things done

Position 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

• 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