Jobs · Information Technology · Illinois

General Manager: Hammitt (Handbags)

Leap · Chicago, IL · 2 wk ago
On-siteInformation Technology$70k–$82k/yrFull-time

About the Brand

Hammitt is a design-forward leather brand, established in Los Angeles to shake up the accessory world with a mix of style and functionality. Co-founded by visionaries Stephenie Hammitt and Tony Drockton, this line is for bold, creative expressionists and those that are out for more than just a look—Hammitt’s a lifestyle.

About the Role

We are seeking a strategic and visionary General Manager to lead our boutique, powered by the Leap Platform, coming to Armitage Ave May 2026. 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.
  • Able to stand, walk, use ladders, and lift up to 50 lbs.
  • Must be 18+ years of age.

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

  • Unlimited PTO (blackout periods apply)
  • Commission Eligible
  • Healthcare benefits (medical, dental, vision)
  • 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

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