Chicago Estate Advisors | Two Chicago Locations + Off-Site Inventory

Independent Contractor

Compensation: Day Rate + Commission OR Draw Against Commission
Additional Opportunities: Performance Bonuses + Quarterly Profit Sharing After Six Months

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THE POSITION

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Chicago Estate Advisors is seeking an experienced, technically capable and revenue-driven Director of E-Commerce & Digital Sales to take ownership of and significantly grow our digital sales operation.

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This is not simply a product-listing, website or social-media position. We need an e-commerce professional who can turn constantly changing, one-of-one inventory into profitable digital sales.

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The Director will oversee e-commerce supporting both Chicago Estate Advisors locations, as well as estate inventory, buyouts, consignments, off-site client inventory, online-exclusive merchandise and other inventory opportunities.

You will be expected to work between locations as business needs require and create enough structure to maintain accuracy without slowing down the business.

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OUR E-COMMERCE ECOSYSTEM

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Wix is intended to serve as our central e-commerce hub, working with Clover and distributing eligible merchandise across appropriate digital channels.

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Our ecosystem includes:

• Chicago Estate Advisors Online Shopping

• eBay

• Instagram

• TikTok

• YouTube

• Pinterest

• Google Shopping

• Other financially worthwhile marketplaces

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The intended workflow is:

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Clover / Inventory Intake → E-Commerce Enrichment → Wix → Online & Marketplace Distribution → Purchase → Sales Attribution → Inventory Update → Delisting → Fulfillment → Reporting

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The Director is responsible for making this system as reliable, efficient and profitable as possible.

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IMMEDIATE PRIORITY: FIX WHAT IS NOT WORKING

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Chicago Estate Advisors has invested in substantial e-commerce infrastructure, but some integrations and automated processes require improvement.

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The Director will audit and troubleshoot systems involving Wix, Clover, eBay, social commerce, Google Shopping and other connected platforms.

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Potential issues include:

• Products failing to publish

• Feed and integration failures

• Inventory discrepancies

• Pricing errors

• Duplicate listings

• Incorrect categories or SKUs

• Shipping errors

• Marketplace rejections

• Social-commerce catalog problems

• Sold merchandise remaining online

• Automatic delisting failures

• Broken automation

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The Director should understand integrations, product feeds, APIs, inventory mapping and automation well enough to identify problems, determine solutions, oversee implementation and verify results.

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We aren't hiring someone to work around broken systems. We're hiring someone to fix them.

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SOLD MEANS SOLD EVERYWHERE

 

Much of our inventory is one-of-one.

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When merchandise sells through Clover, it should be removed or deactivated from applicable online channels as quickly and reliably as possible. Online sales must also update internal inventory and applicable channels.

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Where full automation isn't possible, the Director must establish dependable safeguards.

One item cannot be sold twice.

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INVENTORY & LISTING MANAGEMENT

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The Director will work with existing team members who assist with inventory intake, SKU creation, photography, pricing and product identification, while owning the final e-commerce standard.

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Responsibilities include:

• Verify product information

• Improve or coordinate photography

• Obtain measurements

• Research designers and manufacturers

• Document condition

• Write and improve titles and descriptions

• Optimize keywords and SEO

• Confirm pricing and SKUs

• Confirm inventory location

• Identify buyout vs. consignment

• Establish appropriate shipping/delivery configuration

• Determine appropriate sales channels

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ONE BRAND. ONE STANDARD

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The Director will establish a Chicago Estate Advisors Digital Listing Standard covering:

Photography • Titles • Descriptions • Measurements • Condition • Designer/Manufacturer Identification • Categories • Keywords • SEO • Pricing • SKUs • Inventory Location • Ownership/Consignment • Shipping • Delivery

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Different merchandise and different locations should still result in one consistent Chicago Estate Advisors presentation.

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EXISTING CATALOG CLEANUP

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The Director should expect to inherit an existing catalog requiring improvement, including:

• Inconsistent photography

• Missing measurements

• Weak descriptions

• Incorrect categories

• Missing condition information

• Weak SEO

• Shipping problems

• Duplicate products

• SKU inconsistencies

• Inventory-location discrepancies

• Marketplace synchronization issues

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The goal is to improve the existing catalog while continuing to get new merchandise online.

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TEAM MEMBER 30-ITEM ONLINE SALES PROGRAM

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Participating team members may select up to 30 eligible active items to personally champion online.

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They provide merchandise selection, photography, measurements, information, pricing and location. The Director professionally reviews, standardizes and publishes the listings.

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When an item sells online, sales may be attributed to the originating team member under the company's internal sales-credit program.

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BUYOUT & CONSIGNMENT INVENTORY

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The Director must maintain clear ownership and attribution throughout the merchandise lifecycle.

This includes accurate:

• Client/consignor information

• SKUs

• Pricing

• Ownership designation

• Physical location

• Sale attribution

• Markdown authorization

• Final selling price

• Client payment information

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Intake → Ownership → Pricing → Labeling → Inventory System → Digital Distribution → Sale → Delisting → Attribution → Client Payment

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“YOUR HOUSE, OUR HOUSE, TO YOURS”

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Chicago Estate Advisors can market eligible client merchandise digitally while it remains at the client's home.

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The Director will help develop this into a scalable revenue channel while maintaining accurate client attribution, inventory status, location, pricing, photography, measurements, fulfillment and sales information.

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SEO, SOCIAL COMMERCE & CUSTOMER DEVELOPMENT

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The Director will optimize product titles, descriptions, SEO, Google feeds, eBay specifics, marketplace attributes and images to improve product discovery.

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Instagram, TikTok, YouTube and Pinterest should also be evaluated as potential revenue-producing channels.

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The Director will collaborate with the Social Media Director to connect:

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Social Media = Content, Audience, Storytelling & Traffic

E-Commerce = Catalog, Conversion, Inventory, Fulfillment & Revenue

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The Director will also evaluate and utilize:

• Email marketing

• Customer segmentation

• Wish lists

• Abandoned-cart recovery

• Product recommendations

• New-arrival campaigns

• VIP marketing

• Repeat-customer campaigns

• Collector campaigns

• Interior designer/trade outreach

• Customer re-engagement

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The objective is to understand:

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Who bought? What did they buy? What are they interested in? What might they buy next?

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SHIPPING & FULFILLMENT

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Shipping is a major financial responsibility.

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Merchandise ranges from small collectibles and jewelry to artwork and furniture weighing hundreds of pounds.

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The Director will establish appropriate systems for:

• USPS / UPS / FedEx

• Fragile and insured shipping

• Artwork

• Oversized merchandise

• Local pickup and delivery

• National furniture shipping

• Freight / LTL

• White-glove delivery

• Quote-required shipping

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We do not guess at freight.

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The Director will establish shipping rules, templates, vendor relationships, packing standards and procedures that protect profitability.

The Director is not expected to personally pack every order. The responsibility is to create the system, document it and train the team.

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RETURNS, DAMAGE & CUSTOMER ISSUES

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The Director will establish procedures for:

• Returns

• Cancellations

• Refunds

• Damaged shipments

• Insurance claims

• Lost packages

• Customer disputes

• Chargebacks

• Marketplace claims

• Fraud prevention

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The objective is to protect both customer experience and profitability.

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WIX & CLOVER OWNERSHIP

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We want someone who can continually ask:

What are we using? What aren't we using? What should we be using? What can be automated? What can be integrated? What can generate additional revenue?

The Director should identify capabilities Chicago Estate Advisors is already paying for but not fully utilizing.

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INVENTORY AGING & SELL-THROUGH

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The Director will identify merchandise that isn't performing and recommend appropriate action:

Reprice → Re-photograph → Rewrite → Re-market → Move Channels → Promote → Bundle → Markdown → Auction

Inventory should not simply sit online indefinitely.

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ANALYTICS & PROFITABILITY

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Gross sales alone are not enough.

The Director will monitor:

• Gross and net online sales

• Company revenue and gross margin

• Revenue by platform and inventory source

• Average order value

• Conversion rate

• Sell-through

• Inventory aging

• Marketplace fees

• Shipping collected vs. actual cost

• Advertising expense and ROAS

• Returns/refunds

• Customer acquisition

• Repeat customers

Revenue without margin is not success.

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DIGITAL INVENTORY AUDITS

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Establish recurring audits comparing:

Physical Item ↔ SKU ↔ Clover ↔ Wix ↔ Online Store ↔ Marketplaces

Audits should verify availability, pricing, location, ownership, attribution, measurements, shipping and listing accuracy.

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ACCOUNT SECURITY

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Chicago Estate Advisors must retain appropriate ownership and administrative control of all e-commerce accounts, domains, catalogs, advertising accounts, customer databases and integrations.

Security, two-factor authentication, recovery procedures and backup access must be maintained.

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E-COMMERCE OPERATIONS MANUAL

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The Director is required to create and maintain a comprehensive Chicago Estate Advisors E-Commerce Operations Manual.

It should document applicable procedures for:

• Wix and Clover

• SKUs and listings

• Photography and measurements

• Buyouts and consignments

• Team-member 30-item program

• “Your House, Our House, to Yours”

• Marketplaces and social commerce

• Shipping, packing and freight

• Fulfillment and delisting

• Returns and claims

• Customer communication

• Reporting

• Troubleshooting

• Emergency procedures

The first comprehensive version should be completed during the initial 90 days.

The Director must also train backup personnel.

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TRAIN THE TEAM — DON'T BECOME THE BOTTLENECK

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The goal is not to create an operation where every question requires one person.

Create the Standard → Document It → Train the Team → Delegate → Audit → Improve

We want someone who makes the company more capable and less dependent on any one individual.

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FIRST 90 DAYS

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DAYS 1–30 — AUDIT & STABILIZE

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Audit Wix, Clover, the digital catalog, eBay, social commerce, Google Shopping, integrations, shipping, inventory synchronization, delisting, customer data and analytics.

Provide ownership with:

What Works | What Doesn't | Why | What Can Be Repaired | What Should Be Replaced | What Can Be Automated | What Requires Human Oversight

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DAYS 31–60 — STANDARDIZE & BUILD

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Establish listing, photography, shipping, marketplace, consignment, customer segmentation, reporting and inventory-audit standards.

Train the team.

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DAYS 61–90 — SCALE

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Aggressively improve:

• Online inventory

• Conversion

• Marketplace performance

• Social commerce

• Email/customer marketing

• Off-site consignment sales

• Inventory turnover

• Repeat-customer revenue

Complete the initial E-Commerce Operations Manual.

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QUALIFICATIONS

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Strong preference for hands-on experience with:

• Wix e-commerce — REQUIRED

• Clover or comparable POS/inventory systems

• eBay

• Instagram/Meta Commerce

• TikTok

• YouTube

• Pinterest

• Google Shopping

• Marketplace integrations

• APIs/product feeds/connectors

• Multi-channel inventory synchronization

• SEO / marketplace SEO

• Email marketing

• CRM and customer segmentation

• Analytics

• Shipping/freight

• Fulfillment

• SOP development

• Team training

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Experience with one-of-one, non-replenishable merchandise is strongly preferred, particularly estate property, furniture, art, jewelry, luxury resale, antiques, vintage, fashion, collectibles, consignment or auctions.

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WHO WILL SUCCEED HERE?

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We need someone who is:

• Technical enough to diagnose integrations

• Commercial enough to understand profit

• Creative enough to sell unusual merchandise

• Organized enough to manage consignment

• Detail-oriented enough to prevent inventory mistakes

• Collaborative enough to work across two locations

• Confident enough to establish standards

• Practical enough to fix problems

• Strategic enough to build systems that don't require them to personally do everything

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Most importantly: WE NEED SOMEONE WHO TAKES OWNERSHIP.

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COMPENSATION

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OPTION 1 — DAY RATE + COMMISSION

Negotiated contractual day rate plus commission on qualifying digitally generated sales.

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OPTION 2 — DRAW AGAINST COMMISSION

For a highly sales-driven candidate, a negotiated draw-against-commission structure may be considered.

Final draw, commission rate, calculations, thresholds and reconciliation terms will be established in the independent-contractor agreement.

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PERFORMANCE BONUSES & PROFIT SHARING

Individual performance bonuses may be available based on established digital sales and operational goals.

After six months of continuous engagement, the Director may become eligible for Chicago Estate Advisors' quarterly company profit-sharing program.

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Chicago Estate Advisors currently designates 5% of qualifying company profits for a quarterly bonus pool shared among eligible team members.

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Potential performance measures include:

• Online revenue growth

• Digital profitability

• Sell-through

• Inventory turnover

• Growth of “Your House, Our House, to Yours”

• Customer acquisition

• Repeat-customer revenue

• Marketplace expansion

• Achievement of digital sales targets

Day Rate or Draw + Digital Sales Commission + Performance Bonus Opportunity + Quarterly Profit Sharing

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THE BOTTOM LINE

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Chicago Estate Advisors already has the inventory, retail locations, estate-sale pipeline, consignors, buyout opportunities, customers, brand, digital platforms and team.

We need someone who can connect those pieces into one scalable, profitable e-commerce operation.

Organized enough to control it.
Fast enough to sell it.
Technical enough to connect it.
Commercial enough to protect the profit.
Creative enough to grow it.

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TO APPLY

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Please submit your résumé and complete the Chicago Estate Advisors Director of E-Commerce & Digital Sales 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.

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DIRECTOR OF E-COMMERCE & DIGITAL SALES — CANDIDATE QUESTIONNAIRE

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

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CANDIDATE INFORMATION

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Full Name:
Phone:
Email:
City/State:
LinkedIn:
Portfolio/Website:

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1. ★ WIX EXPERIENCE — REQUIRED

How many years of hands-on Wix experience do you have?

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

★ Have you personally managed a Wix e-commerce store?

Yes / No

If NO, you do not meet the minimum requirements for this position.

Briefly describe what you personally managed within Wix, including products, inventory, shipping, SEO, customer data, email, automations, analytics or integrations.

★ Have you personally troubleshot a Wix integration, product feed or inventory synchronization problem?

Yes / No

If yes, describe the problem, cause, solution and result.

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2. CLOVER & INVENTORY

Have you worked with Clover? Yes / No

If yes, describe your experience.

Have you managed inventory that exists simultaneously in physical stores and online? Yes / No

Have you worked with one-of-one or non-replenishable merchandise? Yes / No

If yes, what type?

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3. MULTI-CHANNEL E-COMMERCE

Which platforms have you personally managed?

• Wix

• Company e-commerce website

• eBay

• Instagram/Meta

• TikTok

• YouTube

• Pinterest

• Google Shopping

• Shopify

• Other

Have you managed inventory synchronization across multiple sales channels? Yes / No

Have you implemented automatic inventory updates or delisting when a one-of-one item sells? Yes / No

★ If Wix, Clover, eBay, Instagram, TikTok, YouTube, Pinterest and other connected channels were not communicating properly, what would your first steps be to identify the breakdown?

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4. EBAY

How many years of hands-on eBay selling experience do you have?

None / Less than 1 year / 1–2 years / 3–5 years / 5+ years

Have you personally managed eBay listings, item specifics, categories, pricing, offers, shipping and marketplace SEO? Yes / No

Have you sold furniture, artwork, jewelry, antiques, collectibles, luxury goods or other one-of-one merchandise through eBay? Yes / No

If yes, describe your experience.

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5. SHIPPING & FREIGHT

Which have you personally managed?

USPS / UPS / FedEx / Dimensional Weight / Insurance / Fragile Shipping / Artwork / Furniture / Oversized / LTL Freight / White-Glove / Local Delivery / National Delivery / Quote-Required Shipping

★ A 400-pound piece of furniture is listed online and the marketplace calculates shipping at $78, while actual freight may cost $1,500–$2,000. What do you do before allowing the transaction to complete?

How would you prevent inaccurate automated shipping charges from creating losses in the future?

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6. PRODUCT PRESENTATION

Are you comfortable establishing standards for photography, measurements, descriptions, titles, keywords, condition and online presentation?

Yes / No

★ Multiple team members contribute photos, measurements and descriptions. How would you create one consistent Chicago Estate Advisors presentation while keeping inventory moving quickly?

Are you comfortable correcting, re-photographing, re-measuring or rewriting listings?

Yes / No

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7. CONSIGNMENT & INVENTORY

Have you managed consignment inventory where some merchandise belongs to the company and some belongs to individual clients?

Yes / No

★ How would you ensure a consigned item remains tied to the correct client, SKU, location, price and final client payment from intake through sale?

Are you comfortable reconciling Clover, Wix and separate consignment records?

Yes / No

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8. DIGITAL MARKETING & CUSTOMER DEVELOPMENT

Which have you personally managed?

Email Lists / Customer Segmentation / Abandoned Cart / Wish Lists / VIP Campaigns / Repeat-Customer Campaigns / Product Recommendations / Google Shopping / Marketplace SEO / Social Commerce / Paid Advertising / Retargeting

How would you use purchase history, wish-list activity and customer interests to generate repeat sales?

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9. ANALYTICS & PROFITABILITY

What e-commerce metrics do you consider most important when determining profitability?

What is the largest monthly online sales volume you have personally managed or materially contributed to?

Have you personally been responsible for an online revenue or profitability goal?

Yes / No

If yes, what was the target and result?

How would you determine whether a marketplace or digital channel is profitable enough to continue investing in?

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10. ★ PROBLEM SOLVING

Describe one significant e-commerce problem you personally diagnosed and solved.

Include:

• What was wrong?

• What caused it?

• What did you change?

• What was the measurable result?

If you inherited a catalog with inconsistent photography, missing measurements, duplicate listings, incorrect shipping and inconsistent descriptions, what would you tackle first and why?

Are you comfortable recommending that an existing integration be replaced rather than repaired when appropriate?

Yes / No

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11. TRAINING & DOCUMENTATION

Have you created SOPs, training manuals or operational documentation?

Yes / No

★ Are you comfortable creating and maintaining a comprehensive Chicago Estate Advisors E-Commerce Operations Manual?

Yes / No

Are you comfortable training store team members on photography, measurements, product submissions, packing and shipping?

Yes / No

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12. TWO-LOCATION & OFF-SITE RESPONSIBILITY

Are you comfortable working between both Chicago Estate Advisors locations and applicable off-site inventory?

Yes / No

Are you comfortable operating in a fast-moving environment involving estate inventory, buyouts, consignments and constantly changing priorities?

Yes / No

Are you comfortable working under an independent contractor agreement?

Yes / No

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13. COMPENSATION

Which structure would you prefer?

Day Rate + Commission / Draw Against Commission / Open to Either

What day rate or draw are you seeking?

What commission structure would you consider appropriate for this position?

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14. COMMUNICATION & RESPONSIVENESS

Chicago Estate Advisors does not expect continuous availability. However, occasional time-sensitive online sales, shipping issues, inventory conflicts, technical problems or customer matters may require a brief response outside normal working hours.

Are you comfortable returning an occasional text or phone call in these circumstances?

Yes / No

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15. ★ TECHNOLOGY & CONTINUOUS IMPROVEMENT

Give an example of an e-commerce feature, automation, integration or technology you discovered a company was underutilizing. What did you do and what was the result?

How do you stay current with Wix, eBay, social commerce, marketplace requirements and e-commerce technology?

Have you appropriately used AI tools within an e-commerce operation?

Yes / No

If yes, explain.

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16. ★ EXPERIENCE & PROOF OF RESULTS

Provide up to three links to online stores, marketplace accounts or e-commerce operations you personally managed or significantly contributed to.

For each, explain your responsibility.

★ Provide one or two measurable results from your previous e-commerce work.

Examples:

• Revenue growth

• Improved conversion

• Increased sell-through

• Reduced shipping losses

• Improved inventory accuracy

• Marketplace expansion

• Increased repeat customers

• Improved SEO/organic traffic

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17. FINAL QUESTIONS

Why are you interested in Chicago Estate Advisors specifically?

What would be your strongest contribution to this position?

Which responsibility would present the greatest learning curve for you?

Is there anything in the position description that you currently do not know how to perform?

Yes / No

If yes, please explain.

If selected, when would you be available to begin?

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REQUIRED ACKNOWLEDGMENT

Please confirm that you understand:

• Hands-on Wix e-commerce experience is required.

• The position supports both retail locations and applicable off-site inventory.

• Chicago Estate Advisors handles buyouts, consignments and one-of-one merchandise.

• This is an independent contractor position.

• Compensation will be Day Rate + Commission OR Draw Against Commission.

• Accurate inventory synchronization, shipping, freight and delisting are critical.

• You will establish and maintain consistent e-commerce standards.

• You will diagnose and improve Wix, Clover, eBay and social-commerce integrations.

• You will collaborate with and train existing team members.

• You will create and maintain the E-Commerce Operations Manual.

• Occasional reasonable responsiveness may be required for time-sensitive e-commerce matters.

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Applicant Name:
Date:

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INTERNAL REVIEW — PRIORITY SCREENING

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Review the ★ questions first:

★ Wix e-commerce experience — Has personally managed Wix e-commerce
★ Wix troubleshooting — Has actually troubleshot Wix integrations
★ Multi-channel troubleshooting — Can diagnose communication failures
★ Shipping/freight — Understands shipping risk and profit protection
★ Catalog consistency — Can establish standards across multiple contributors
★ Consignment — Understands tracking and reconciliation
★ Problem solving — Demonstrates genuine e-commerce troubleshooting ability
★ Operations Manual — Can create and maintain documentation
★ Technology — Demonstrates initiative and ability to identify underutilized technology
★ Proof of results — Provides previous work and measurable results

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IMMEDIATE SCREENING RULE

If the applicant answers NO to the Wix e-commerce experience question, they do not meet the minimum requirements and the remainder of the application does not need to be reviewed.