General Manager: LEAP (Menswear)

 About the Role

We are seeking a strategic and visionary General Manager to lead a menswear boutique, powered by the Leap Platform, in Chicago. This role is designed for an accomplished retail leader who excels at full business ownership—driving profitable growth, strengthening brand presence, and building a high-performing team.

As General Manager, you are accountable for the overall performance and long-term success of the business. In partnership with your leader, you’ll translate brand strategy into actionable plans that drive revenue, deepen client loyalty, and position the boutique as a destination within the local market. Through a visible and confident leadership presence, you will set clear expectations, foster accountability, and cultivate a culture rooted in service excellence and results.

You will elevate client engagement through thoughtful, data-informed strategies that strengthen retention and expand lifetime value. As a market leader, you will identify opportunities to grow awareness through community partnerships, localized outreach, and strategic activations.

You will also ensure disciplined execution across all core business functions—including talent planning, scheduling, visual presentation, inventory management, and financial oversight—balancing operational rigor with an exceptional in-store experience. This role requires strong business judgment, executive-level communication, and the agility to lead in a dynamic retail environment.

In partnership with Leap and neighboring boutiques, you may also contribute to cross-store initiatives and new store openings.

Position Requirements

• 5+ years of progressive retail leadership experience with full accountability for sales performance, team development, and operational management.
• Proven success in premium, luxury, or high-touch retail environments.
• Strong financial and business acumen, with the ability to analyze performance metrics and adjust strategy to drive sustained growth.
• Demonstrated ability to hire, develop, and retain high-performing teams while building leadership bench strength.
• Expertise in cultivating meaningful client relationships that drive loyalty and long-term revenue.
• Executive presence with strong communication and influencing skills across teams and cross functional partners.
• Operational discipline across payroll, inventory, visual standards, compliance, and expense management.
• Entrepreneurial mindset with the ability to identify opportunities, solve complex challenges, and lead through change.
• Proficiency with Shopify, CRM (Endear), Slack, and Google Workspace.
• Flexible availability, including evenings, weekends, holidays, and occasional travel.
• Ability to actively lead on the sales floor, including standing, walking, using ladders, and lifting up to 50 lbs.
• Must be 18+ years of age.

Starting Pay: $70,000 annual. Actual compensation will be based on experience, qualifications, and skills. This position is bonus eligible.

Key Performance Indicators (KPIs)

• Sales & Profitability: Achieves or exceeds revenue targets while optimizing conversion, AOV, and UPT.
• Client Loyalty: Strengthens retention and repeat business through elevated engagement strategies.
• Operational Performance: Maintains inventory accuracy, brand standards, and financial controls.
• Talent Outcomes: Builds an engaged team with strong retention and internal growth.

About Leap

The Leap platform powers insight-driven retail stores for modern brands, delivering superior performance with minimized risk. We manage 100+ stores across the country proudly partnering with trailblazing brands such as Frankies Bikinis, Grown Brilliance, Malbon Golf, MZ Wallace, Ring Concierge, SET and many others. To hear more about our platform directly from our CEO, click here!

Leap offers a competitive total rewards package, which includes:

• Unlimited PTO (blackout periods apply)
• Commission 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

However you identify, whatever your path to get here; Leap celebrates diversity and is committed to maintaining a safe, rewarding and inclusive environment where Leapers thrive individually and as a team. In order to achieve our mission, building the world's largest network of branded retail stores – powered by data, systems and scale; we need to work hard to foster a diverse community to support the brands and customers we serve. These aren't just words, this is who we are. We know that our differences are what make our organization special and are paramount to our culture. Your age, skin color, beliefs, sexual orientation, nationality, disability, parental status, vet status, gender identity are valued.