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Assistant Store Manager

Water Tower Place | Chicago’s Magnificent Mile
Independent Contractor

$200/DAY + 3% COMMISSION ON INDIVIDUAL IN-STORE SALES + $1,500 MONTHLY TEAM PERFORMANCE BONUS + ADDITIONAL BONUS OPPORTUNITIES

HELP BUILD THE BUSINESS — NOT JUST MANAGE THE STORE

Chicago Estate Advisors is seeking an experienced, organized, creative and sales-driven Assistant Store Manager for our Water Tower Place location.

This is a hands-on leadership position for someone who can SELL, LEAD PEOPLE, CREATE BUSINESS and TAKE OWNERSHIP.

Our ideal candidate may come from luxury retail, resale, consignment, furniture, fashion, jewelry, fine art, interior design, hospitality or another high-touch sales environment.

Unlike traditional retail, Chicago Estate Advisors offers customers designer fashion, jewelry, furniture, artwork, antiques, vintage, collectibles, home décor and one-of-a-kind estate pieces across multiple categories.

THE ROLE

The Assistant Store Manager helps ensure Water Tower Place operates, sells and performs to Chicago Estate Advisors standards.

Key responsibilities include:

  • Lead, coach and motivate the sales team

  • Hold team members accountable for productivity and performance

  • Actively sell and lead by example

  • Coach associates on customer engagement, storytelling, cross-selling, follow-up and closing

  • Monitor daily sales and store goals

  • Keep the sales floor active and productive

  • Ensure opening, closing, Clover POS and Z Report procedures are completed accurately

  • Identify and solve operational problems

  • Communicate clearly with ownership and management

  • Train and develop team members

  • Follow through on assigned responsibilities

  • Help maintain and improve company policies and procedures

When the store is quiet, the team should be creating tomorrow’s sales — not waiting for customers to walk in.

INDIVIDUAL SALES & CLIENT DEVELOPMENT

This is not an administrative management position. The Assistant Store Manager is expected to sell.

In addition to the $200 contractual day rate, the Assistant Store Manager earns 3% commission on qualifying merchandise personally sold through the Water Tower Place physical retail store, including Chicago Estate Advisors-owned/buyout and consigned merchandise.

Commission is calculated on the merchandise selling price before applicable sales tax.

The successful candidate should be comfortable selling everything from a $25 find to a $5,000, $10,000 or substantially higher-value piece.

We also expect the Assistant Store Manager to help establish a strong clienteling culture, including:

  • Learning customers’ interests, designers, artists and styles

  • Identifying what customers collect or are furnishing

  • Maintaining appropriate customer information

  • Following up with customers

  • Contacting clients when relevant merchandise arrives

  • Identifying VIP and high-potential customers

  • Teaching the sales team to do the same

 

Our goal is for customers to think:

“Before I buy it somewhere else, I should call my person at Chicago Estate Advisors.”

COMMUNITY OUTREACH & BUSINESS DEVELOPMENT

Our business cannot depend solely on walk-in traffic.

The Assistant Store Manager will identify and develop relationships with:

  • Luxury residential buildings and condominiums

  • Interior designers and decorators

  • Real estate professionals

  • Residential concierge and management teams

  • Hotels and hospitality businesses

  • Corporate relocation professionals

  • Nearby hospitals and medical professionals

  • Collectors and dealers

  • Local businesses and professional organizations

  • Conference and tourism traffic

Continually ask:

WHO AROUND US SHOULD KNOW CHICAGO ESTATE ADVISORS EXISTS?

Then help us reach them.

WEEKLY TRAFFIC-BUILDING INITIATIVES

The store should continually give customers a reason to return.

The Assistant Store Manager is expected to help create at least one meaningful traffic-building initiative every week, such as:

  • Featured collection or designer spotlight

  • New-arrival presentation

  • Personal-shopping initiative

  • Community partnership

  • Client outreach campaign

  • Social-media promotion

  • Special merchandise showcase

  • Cross-promotion with a neighboring business

  • Targeted customer invitations

 

MONTHLY EVENTS & PROMOTIONS

The Assistant Store Manager will also help develop and execute at least one meaningful customer-driving event or promotion each month.

Potential concepts include book signings, fashion presentations, designer showcases, tastings, entertainment, community partnerships and special collection events.

Promotions may also include concentrated events such as a two-hour 75% OFF sale rather than unnecessarily discounting merchandise for an entire weekend.

The goal isn't simply to have an event. The goal is to create traffic that creates sales.

VISUAL MERCHANDISING

Our inventory changes constantly, and the presentation should change with it.

The Assistant Store Manager will:

  • Refresh merchandise regularly

  • Create compelling displays and focal points

  • Feature new arrivals

  • Reposition stagnant merchandise

  • Identify visually stale areas

  • Maintain a polished presentation

 

Visual merchandising is a sales tool.

CONSIGNMENT & INVENTORY

Water Tower Place carries both Chicago Estate Advisors-owned/buyout inventory and client consignments.

The Assistant Store Manager will help maintain accurate records involving:

  • Client information

  • Consignment inventory

  • SKUs

  • Pricing

  • Item status

  • Sales

  • Client payouts

  • Supporting documentation

Inventory accuracy directly affects our clients, accounting and reputation.

TECHNOLOGY

Candidates should be comfortable with or able to quickly learn:

  • Clover POS

  • Wix

  • Shopify

  • Excel

  • QuickBooks or comparable systems

  • Customer/client tracking systems

  • Digital inventory and consignment records

You do not need to know every platform on day one. You do need to be technologically confident, organized and able to learn quickly.

POLICIES, ACCOUNTABILITY & LOSS PREVENTION

The Assistant Store Manager is responsible for helping ensure established policies and procedures are followed.

This includes:

  • Delegating responsibilities and following up

  • Addressing performance problems

  • Identifying better processes and recurring problems

  • Helping maintain and expand the company Policies & Procedures Manual

  • Protecting merchandise, client property and company assets

  • Monitoring cash, keys, restricted areas, POS activity and security systems

  • Immediately escalating significant irregularities

If someone is absent, the business should still know exactly what to do.

BRING US YOUR IDEAS

One of the biggest differences between Chicago Estate Advisors and traditional corporate retail is the opportunity to help shape the business.

If you have an idea for an event, partnership, merchandising concept, client-development strategy, community relationship, operational improvement or sales initiative:

WE WANT TO HEAR IT.

See something that isn't working? Bring us a solution.

Build a successful program? Help us grow it.

Develop strong customer relationships? Keep developing them.

We aren't looking for someone to simply execute someone else's playbook. We want someone capable of helping us write the next one.

COMPENSATION

$200 CONTRACTUAL DAY RATE

Paid for accepted shifts.

3% INDIVIDUAL SALES COMMISSION

3% on qualifying merchandise personally sold through the Water Tower Place physical retail store, including qualifying owned/buyout and consigned merchandise. Calculated before applicable sales tax.

$1,500 MONTHLY TEAM PERFORMANCE BONUS

When the entire Water Tower Place sales team reaches $60,000 in monthly Clover-collected sales, the Assistant Store Manager becomes eligible for an additional $1,500 monthly management performance bonus, provided established management and operational requirements are satisfied.

Management performance includes:

  • Sales leadership

  • Staff productivity and accountability

  • Client development

  • Community outreach

  • Weekly traffic initiatives

  • Monthly event/promotion execution

  • Visual merchandising

  • Consignment accuracy

  • Operational standards

  • Policy compliance

  • Loss prevention

  • Communication and follow-through

 

Your 3% commission rewards what YOU personally sell.


Your $1,500 bonus rewards your ability to help the ENTIRE STORE succeed.

QUARTERLY COMPANY-WIDE PROFIT SHARING

After six months of continuous engagement, eligible team members may participate in Chicago Estate Advisors’ quarterly company-wide profit-sharing program according to applicable program terms.

Chicago Estate Advisors currently allocates 5% of qualifying company net profit to a quarterly team bonus pool shared among eligible team members.

WHO WE WANT TO MEET

We are particularly interested in candidates with experience in:

  • Luxury or specialty retail

  • Luxury resale or consignment

  • High-ticket sales

  • Furniture and interior design

  • Fine art

  • Jewelry

  • Antiques and vintage

  • Fashion and accessories

  • Personal shopping/clienteling

  • Visual merchandising

  • Retail operations

  • Inventory management

  • Community outreach

  • Event development

  • Business development

You should be:

  • Sales-driven and professional

  • Highly organized

  • Confident managing people

  • Comfortable holding people accountable

  • Self-motivated, creative and resourceful

  • Technologically capable

  • Strong at client development

  • Comfortable selling high-value merchandise

  • Capable of coaching salespeople

  • Detail-oriented and able to manage multiple priorities

  • Productive without constant supervision

  • Able to identify problems and move toward solutions

MOST IMPORTANTLY: WE NEED A LEADER WHO CAN SELL.

WHAT SUCCESS LOOKS LIKE

Success isn't simply keeping the store open.

Success looks like:

  • Improving daily sales performance

  • Coaching the team

  • Following up with customers

  • Developing new client relationships

  • Refreshing stagnant merchandise

  • Creating weekly traffic initiatives

  • Developing monthly events

  • Building community partnerships

  • Correcting inventory or consignment discrepancies

  • Improving operational procedures

  • Helping other salespeople close significant transactions

  • Personally producing sales and earning commission

  • Helping the team reach $60,000 and earning the $1,500 management bonus

WHY CHICAGO ESTATE ADVISORS?

If you know luxury retail, you understand exceptional products, presentation and customer experiences.

Chicago Estate Advisors gives you the opportunity to take those skills further through:

  • Broader merchandise categories

  • More entrepreneurial freedom

  • Greater influence over the business

  • Client development across multiple luxury categories

  • Event and community partnership opportunities

  • $200 contractual day rate

  • 3% individual qualifying in-store sales commission

  • $1,500 monthly team-performance opportunity

  • Company-wide profit sharing after eligibility requirements are met

 

HELP GROW THE BUSINESS — AND PARTICIPATE FINANCIALLY IN THE RESULTS YOU HELP CREATE.

WE AREN'T HIRING SOMEONE TO WATCH THE STORE.
WE ARE HIRING SOMEONE TO HELP BUILD IT.

TO APPLY

Please submit your résumé and complete the Chicago Estate Advisors Assistant Store Manager Candidate Questionnaire.

Selected candidates will be contacted regarding the next stage of the interview process. Email this information to deb@chicagoestateadvisors.com, admin@chicagoestateadvisors.com and andy@chicagoestateadvisors.com

 

ASSISTANT STORE MANAGER — CANDIDATE QUESTIONNAIRE

Water Tower Place | Chicago’s Magnificent Mile

Thank you for your interest in the Assistant Store Manager position.

This is a hands-on sales and leadership position. We are looking for someone who can sell, manage people, develop new business, create customer traffic and take ownership of store operations.

Please answer all questions. Questions marked ★ are priority screening questions.

1. ★ MANAGEMENT EXPERIENCE

How many years of retail, sales or business-management experience do you have?

Less than 1 year / 1–2 years / 3–5 years / 5–10 years / 10+ years

What is the largest team you have directly managed?

Briefly describe your most relevant management experience.

2. ★ PERSONAL SALES PERFORMANCE

What is the highest amount of sales you have personally generated in a single month?

Under $10,000 / $10,000–$24,999 / $25,000–$49,999 / $50,000–$99,999 / $100,000+ / Personal sales were not tracked

If known, what were your approximate average monthly personal sales?

What is the highest-priced item or service you have personally sold?

3. ★ MANAGING AN UNPRODUCTIVE SALES FLOOR

You walk onto the sales floor and find two team members sitting behind the counter. Customer traffic is slow and neither employee is doing anything productive.

What do you do? Please be specific.

4. ★ ACCOUNTABILITY

You gave a team member clear instructions regarding an important responsibility. Later, you discover it was not completed.

How would you handle the situation?

What would you do if the same behavior happened repeatedly?

5. ★ BUILDING SALES FROM $25,000 TO $60,000

Imagine you inherit a retail location currently generating approximately $25,000 per month in collected sales.

Your goal is to help develop that location toward $60,000 per month.

What would your first 90 days look like? What specific actions would you take to increase sales, develop customers, improve the team and generate new traffic?

© 2026 Chicago Estate Advisors.

Auctions conducted in partnership with a licensed Illinois auction firm.Licensed Auction Firm: Direct Auction Galleries Inc (IL License #444.000498). Managing Auctioneer: John R. Modica.

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