PT Sales Supervisor: Hammitt (Handbags)

Leap; Chicago (IL); On-site; USD 31,684 - 35,817; Part time

Benefits offered by this job

Bonus eligible

Medical, Dental & Vision benefits

401K

Accrued PTO

Employee discount

Job summary

A modern retail management platform is seeking a passionate PT Sales Supervisor in Chicago. You will oversee daily business operations while inspiring a high-performing team. This role requires strong leadership skills and a knack for customer relationship management to drive sales and ensure operational excellence. Compensation ranges from $23 to $26 per hour based on experience, with additional perks like medical benefits and employee discounts. Apply now to be part of a dynamic and evolving retail environment.

Qualifications

• Prior leadership or supervisory experience in retail.
• Proven ability to deliver exceptional client experiences.
• Comfort navigating evolving business needs.

Responsibilities

• Lead a high-performing team and support daily operations.
• Drive sales performance and elevate customer service.
• Execute strategic initiatives to increase revenue.

Skills

Leadership in retail

Client relationship management

Strong selling skills

Attention to detail

Team collaboration

Organizational skills

Tools

Shopify

Endear

Slack

Job description

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. It all started back in 2008 when Stephenie set out to redefine luxury handbags, aiming for leather that felt as good as it looked, hardware that shimmered, and designs that mixed classic with cool. These early years established a pride that ignites in its wearers, a passion for bringing people together, and relentless attention to detail that’s manifested into a movement.

About the Role

We are seeking a passionate and driven PT Sales Supervisor for our boutique coming to Armitage Ave in May 2026. As a key member of the leadership team, you will support the Store Leader/General Manager in driving daily business operations, sales performance, and an elevated, service-first culture. This role blends hands‑on leadership with strong business execution. You will lead from the sales floor—coaching, motivating, and developing associates in real time to deliver personalized, memorable client experiences. Through clear communication, thoughtful feedback, and a collaborative mindset, you will help foster a high‑performing team environment rooted in accountability, professionalism, and brand pride. You will partner closely with store leadership to execute strategic initiatives that increase revenue, strengthen client retention, and uphold operational excellence. Responsibilities include supporting inventory management, visual merchandising, shipment processing, and ensuring all brand standards are executed with precision and attention to detail. With a one‑team mindset, you will also contribute to broader market and brand initiatives such as promotional events, activations, and store openings. Comfortable operating in a dynamic, fast‑paced environment, you will leverage tools such as Shopify, Endear, and Slack to support client outreach, team communication, and business operations.

Position Qualifications

• Prior leadership or supervisory experience in retail or customer‑focused environments, with a demonstrated ability to inspire, coach, and develop team members.
• Proven ability to deliver exceptional, personalized client experiences and build authentic customer relationships that drive loyalty and results.
• Strong selling skills with the ability to anticipate client needs, overcome objections, and consistently achieve personal and team sales goals.
• Entrepreneurial and adaptable mindset, with comfort navigating evolving business needs while maintaining focus and accountability.
• Collaborative team player who communicates clearly, provides constructive feedback, and builds strong cross‑functional relationships.
• Professional presence with the ability to handle client inquiries, concerns, and escalations with empathy and sound judgment.
• Strong attention to detail and organizational skills to ensure operational excellence across merchandising, inventory, and daily task execution.
• Flexibility to accommodate dynamic business needs, including availability for days, nights, weekends, and holidays.
• Active and engaged presence on the sales floor, with the physical capability to stand, walk, climb ladders, and lift up to 50 pounds.
• Must be 18 years of age or older.

Hourly Pay Range: $23 to $26. Compensation will be determined based on the candidate's experience, skills, competencies, and qualifications.

Key Performance Indicators (KPIs)

• Sales Performance: Achieves and exceeds personal and team sales goals by optimizing key metrics including Conversion Rate, Units Per Transaction (UPT), and Average Order Value (AOV) through proactive client engagement and strategic selling.
• Client Retention & Experience: Drives strong Net Promoter Scores (NPS), secret shopper results, and repeat business through personalized outreach and relationship‑building.
• Operational Excellence: Demonstrates strong organizational and time‑management skills, ensuring tasks are completed accurately and on time while maintaining brand standards.

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 Billy Reid, Frankies Bikinis, Grown Brilliance, Malbon Golf, MZ Wallace, Paper Planes, Ring Concierge, SET and many others.

Leap Perks

• Bonus eligible
• Medical, Dental & Vision benefits (must average 32+ hours a week)
• AllOne Health - Employee Assistance Programs
• 401K
• Accrued PTO:
  • Full‑time hourly employees can accrue up to two weeks (80 hours) of paid time off annually, excluding restricted dates during busy retail seasons, with manager approval.
  • Part‑Time hourly employees can accrue based on local laws
• Employee discount + wardrobe allotment for participating Leap brands

Equal Employment Opportunity

In order to achieve our mission, we need to work hard to create a diverse community of Leapers to support the brand and customers we serve and help us all grow and thrive individually and as a team. Our differences make our organization special and are paramount to our culture. Your age, skin colour, beliefs, sexual orientation, nationality, disability, parental status, vet status, gender identity are valued.