ChatGPT answers, unedited

Yes. For a retail redesign where the website, inventory, and in-store POS need to operate as one system, I’d avoid firms that are primarily branding/SEO shops and focus on agencies with demonstrated commerce integrations.

My Chicago shortlist

1. Uncap — strongest fit if you’re considering Shopify
   • Chicago-based and heavily focused on Shopify/unified commerce.
   • Specifically positions its work around B2C + B2B + POS, inventory/system integrations, and custom Shopify apps when an off-the-shelf integration isn't enough.
   • Particularly interesting if you want a modern retail site while keeping operations relatively straightforward. fueler.io
   • My first call if Shopify POS is on your shortlist.

2. Praella — strong Shopify/Shopify Plus option
   • Downtown Chicago presence and Shopify/Shopify Plus specialization.
   • Good candidate if the redesign is also a significant UX/brand/commerce transformation rather than simply connecting a new website to your existing POS.

3. Objectwave — best for a more complex/custom build
   • Chicago digital-commerce and software engineering firm with experience across retail/consumer products.
   • I'd put them on the list if you have unusual inventory logic, multiple systems, or need substantial custom software rather than a conventional Shopify implementation.

4. Kensium Solutions LLC — good for back-office-heavy retail
   • Particularly relevant if your project involves ERP + ecommerce + inventory + orders + fulfillment rather than just a website redesign.
   • They work across Adobe Commerce, BigCommerce and Shopify and emphasize unified commerce/integration work.

5. Adage Technologies — strong custom UX/software choice
   • Chicago firm covering strategy, UX, ecommerce, software development, integrations and ongoing support.
   • Worth considering if the redesign needs to be highly customized rather than fitting your business into a standard ecommerce template.

6. Atwix — integration-heavy option
   • Chicago office with a focus on complex ecommerce implementations and connecting commerce platforms to ERP/back-office systems.
   • More appropriate if your inventory/order architecture is complicated.

One smaller specialist I'd also talk to

Ethercycle in nearby Skokie is worth a conversation if you're leaning strongly toward Shopify. They're Shopify-focused and specialize in custom storefront design/development rather than generic web design.

And Chicago Web is unusually relevant if your inventory system is complicated. They explicitly connect Shopify/Magento/WooCommerce to ERP, WMS, 3PL, accounting and inventory systems, including inventory feeds and reservations. chicagoweb.com

Chicago Web

How I'd narrow it down

For a Near North Side independent/multi-location retailer, I'd probably start with:

Uncap → Praella → Chicago Web → Kensium

The key question isn't really "who makes the prettiest website?" It's which system should be the source of truth for products, inventory, customers and orders?

If you're currently on Square, Lightspeed, Shopify POS, Clover, or another POS, tell me which one and roughly how many stores/SKUs you have. I can narrow this to 3 firms that are specifically equipped for your setup and compare their likely strengths, project complexity, and fit.

For a retail redesign with integrated inventory + POS, I’d prioritize firms that understand omnichannel commerce (website + store + inventory + fulfillment), not just visual web design. Since you’re on the Near North Side, these are Chicago-area firms I’d put on a shortlist:

Strong fits for retail + POS/inventory integration

Praella — good if you’re considering Shopify Plus
sweettalk.io

• Chicago-based ecommerce agency focused on Shopify/Shopify Plus.
• Worth talking to if you need a polished storefront, customer experience redesign, migrations, and integrations with retail systems. sweettalk.io

Sweet Talk — especially relevant for store operations
sweettalk.io

• Has retail examples involving POS migrations and syncing inventory between systems like Lightspeed and Shopify. sweettalk.io
• A good conversation if your pain point is “our website and store inventory don’t agree.”

Armia Systems — better for custom integrations
www.armia.comsweettalk.io

• Works on ecommerce builds, POS integrations, and inventory management across online/offline storefronts. www.armia.comsweettalk.io
• Consider them if you have unusual workflows rather than a straightforward Shopify setup.

Americaneagle.com — enterprise/more complex retail

• Larger agency that handles ecommerce, application development, integrations, and ongoing support.
• Better fit if you have multiple locations, a large catalog, or complex back-office requirements.

Makro — strong Shopify Plus candidate
www.makroagency.comsweettalk.io

• Focuses on Shopify Plus builds, custom apps, and integrations for retailers with more complicated catalogs and operations. www.makroagency.comsweettalk.io

Also worth a look

• Atwix — stronger on complex commerce implementations and integrations than a typical design shop.
• BIT Studios — has experience with ecommerce integrations and POS-related builds. www.bitstudios.com
• 10 US Tech Inc. — local engineering-focused team mentioning ecommerce, POS, and API integration work. 10ustech.com

Questions I’d ask every firm before hiring

1. Which POS systems have you integrated with? (Shopify POS, Lightspeed, Square, Clover, NCR, custom ERP, etc.)
2. Can you show a live retail example where inventory syncs both directions?
3. Who owns the integrations and code after launch?
4. How do you handle SKU migration, variants, barcodes, and historical customer data?
5. What happens when the POS says an item is available but the website sells it?
6. Do you provide post-launch support during holiday/peak sales periods?

For a typical independent Chicago retailer, I’d probably start with Sweet Talk, Praella, Makro, and Armia for discovery calls, then compare their proposed architecture before choosing. sweettalk.io

If you tell me your current POS (Shopify POS, Lightspeed, Square, Clover, etc.), number of stores, and whether you’re apparel/home/gifts/food/etc., I can narrow this to the firms most likely to fit.

Yes. For a retail redesign where the website, POS, and inventory need to operate as one system, I’d prioritize firms with actual omnichannel/integration experience—not generic Chicago web-design shops.

My Chicago shortlist

1. Praella - eCommerce Agency — best overall if you're leaning Shopify
   • Chicago office and strong Shopify/Shopify Plus specialization.
   • Good fit if you want a polished redesign plus custom integrations and a scalable commerce platform.
   • Particularly worth interviewing if customer experience/UX is as important as the back-end integration.

2. Uncap — best for inventory/operations complexity
   • Chicago-based and heavily focused on Shopify, B2B and unified commerce.
   • Their offering specifically addresses real-time synchronization of inventory, orders, customers and pricing between Shopify and ERP/warehouse systems. www.makroagency.com
   • I'd put them high on the list if you have multiple locations, a complicated catalog, or an existing ERP/POS that needs to remain in the picture.

3. Americaneagle.com, Inc. — best for a larger/more complex retailer
   • Chicago presence and considerably more enterprise-oriented.
   • They handle ecommerce, UX, development and integrations involving ERP, PIM, POS and other third-party systems.
   • Probably overkill for a small independent retailer, but compelling if this is a substantial operation.

4. Ethercycle — best boutique Shopify option
   • Chicago-area Shopify specialist with an emphasis on custom storefront design/development and ongoing ecommerce support.
   • I'd consider them if you want a more hands-on boutique relationship rather than a large systems integrator.

5. Makro — best for a sophisticated Shopify Plus build
   • Their Chicago practice specifically targets retailers with large catalogs and multi-location inventory, plus ERP/CRM/logistics integrations and POS extensions. www.makroagency.com
   • They're a particularly interesting option if you're expecting significant integration/custom-app work.

6. Soda Web Media — not Chicago-based, so lower priority
   • I wouldn't put them ahead of the Chicago firms, but their retail experience is unusually relevant: they've implemented Lightspeed across multiple stores and synchronized Lightspeed with Shopify for real-time inventory, customer and order data. www.makroagency.comsweettalk.io

One important decision before you call them

If you're currently using something like Square, Lightspeed, Clover, NCR, Shopify POS, or another retail POS, tell each agency exactly what you have. The architecture changes substantially depending on whether you're:

A. replacing the POS with Shopify POS
B. keeping the existing POS and integrating it with a new ecommerce site
C. replacing both POS and ecommerce simultaneously.

For example, Shopify has a documented Chicago retail case with Vin Chicago, where Shopify unified POS, ecommerce, inventory and customer data across three locations. www.shopify.com

My first three calls would be Uncap, Praella, and Makro. I'd ask all three for a proposed architecture before discussing visual design. That's the fastest way to discover whether they're actually capable of solving the inventory/POS problem versus simply making a prettier website.

If you tell me what POS/inventory system you're using now, number of stores, approximate SKU count, and whether you want to move to Shopify, I can narrow this to 2–3 firms and tell you exactly what I'd ask each one.

Yes. For a retail redesign where the website, inventory, and in-store POS need to work as one system, I’d prioritize firms with actual omnichannel/POS integration experience rather than a general Chicago web-design shop.

My shortlist

1. Ice Nine Online — Chicago-based and explicitly focused on Shopify. They build and maintain Shopify sites, and Shopify can provide the ecommerce + POS foundation. icenineonline.com

Best for: a relatively straightforward Shopify/POS modernization where design is still important.

2. Praella - eCommerce Agency — A dedicated ecommerce agency in the Loop. I'd put them on the RFP list if you expect a more sophisticated commerce build rather than a simple website refresh.

3. Sweet Talk — Particularly interesting for your requirements. They've implemented Lightspeed + Shopify, including real-time synchronization of inventory, customers and orders, and have worked with multi-store retailers. sweettalk.iosynectadigital.com

Best for: if you're already on Lightspeed or are considering it.

4. Makro — Their Chicago practice specifically handles Shopify Plus redesigns, custom applications, large retail catalogs, multi-location inventory, and ERP/CRM/logistics integrations. www.makroagency.com

Best for: a larger retailer or complicated back-office/inventory environment.

5. CQL — More of a unified-commerce implementation specialist than a traditional web-design firm. They explicitly offer Shopify POS implementation, hardware/software integration, inventory/catalog synchronization, POS data migration and analytics. www.cqlcorp.com

Best for: making the POS/inventory architecture rock-solid, particularly if the redesign is part of a broader omnichannel project.

6. Uncap — Worth including as another Chicago ecommerce specialist for comparison, particularly if you want a broader ecommerce agency rather than a pure creative shop.

Who I'd contact first

For a Near North Side retailer, I'd probably send an RFP to Ice Nine + Sweet Talk + Praella, and add Makro or CQL if you have multiple locations, a large SKU count, an existing ERP, or complicated inventory rules.

One important distinction: don't let the agencies treat “website redesign” and “POS integration” as two separate projects. Your brief should require a single architecture for:

• ecommerce catalog ↔ POS catalog
• real-time inventory by location
• online orders ↔ store fulfillment/returns
• customer profiles/loyalty
• promotions and pricing
• BOPIS/curbside, if applicable
• sales and inventory reporting
• accounting/ERP integration
• migration of historical products, customers and orders

For example, Synecta describes a Shopify POS setup with real-time physical/online stock synchronization and multi-outlet management, while Sweet Talk has demonstrated Shopify/Lightspeed inventory and order synchronization. sweettalk.iosynectadigital.com

If you tell me your current POS (Shopify, Lightspeed, Square, Clover, etc.), number of stores, and roughly how many SKUs you carry, I can narrow this to 3 firms that are the best fit and give you the questions I'd put in the RFP.

If you’re a Near North Side retailer looking for a redesign where the website, inventory, and in-store POS actually operate as one system, I’d prioritize firms with unified-commerce / Shopify POS / ERP integration experience rather than a general web-design shop.

My Chicago shortlist

1. Uncap — strongest local fit
   • Chicago-based and specifically focused on Shopify/Shopify Plus.
   • Particularly interesting for a retailer because its offering includes ERP/warehouse integration designed to keep inventory, orders, customers and pricing synchronized. digitalheroesco.com
   • I'd put them near the top of your outreach list if your current inventory system is complicated.

2. Praella - eCommerce Agency — strong design + Shopify option
   • Downtown Chicago presence.
   • Shopify/Shopify Plus specialist with UX/UI, custom development, integrations and migrations. Good candidate if the brand/customer experience needs as much attention as the back end.

3. Kensium Solutions LLC — best for complex back-office integration
   • Chicago-based and more integration-heavy than a typical creative agency.
   • Particularly worth talking to if your POS needs to communicate with an ERP, warehouse, accounting, or existing inventory system. Their focus is unified commerce and synchronizing products, inventory, orders and fulfillment.

4. Atwix — enterprise/complex-commerce choice
   • Chicago office and a strong emphasis on ecommerce architecture, integrations and complex buying experiences.
   • I'd consider them if you're a larger retailer or have multiple locations/systems.

5. Americaneagle.com, Inc. — if this is a major transformation
   • Much larger agency than the others, with ecommerce, UX, development and integrations including ERP/PIM/POS.
   • Better suited to a substantial replatform or enterprise-scale project than a straightforward storefront redesign.

Two non-Chicago firms I'd also interview

CQL — Shopify unified-commerce/POS specialists has unusually deep Shopify POS expertise: migration, implementation, hardware/software configuration, inventory/catalog synchronization and staff training. www.cqlcorp.comsolomediagroup.com

Flux Agency — Shopify POS integration is another good benchmark because its offering explicitly unifies ecommerce and physical retail around one inventory and customer database. flux.agency

Who I'd call first

For your situation, my first three calls would be:

Uncap → Praella → Kensium

And I'd make the RFP explicitly ask:

• Can you redesign the storefront without disrupting POS operations?
• Can you make one inventory source of truth for store + online?
• What POS do you recommend, and why?
• Can you integrate our existing inventory/ERP/accounting system, rather than forcing us to replace everything?
• How do returns, exchanges, gift cards and customer profiles work across channels?
• Can store staff see online orders and inventory?
• What happens when inventory goes negative or synchronization fails?
• Who handles POS hardware/network setup and staff training?
• What ongoing support do you provide after launch?

One important point: don't hire a firm solely because it says "Shopify web design." For a physical retailer, the difficult part is usually the systems architecture—inventory, POS, fulfillment, returns and customer data—not the visual redesign. Firms like Uncap, Kensium and CQL are interesting precisely because they advertise that integration layer. www.cqlcorp.comsolomediagroup.com

If you tell me what POS/inventory system you use now (Square, Lightspeed, Shopify, Clover, NCR, etc.), number of stores, and roughly how many SKUs, I can narrow this to the 3 firms I'd actually invite to pitch.

Yes. For a retail redesign where the website, POS, and inventory need to operate as one system, I’d prioritize commerce/integration specialists over a conventional branding-first web design shop.

My Chicago shortlist

1. Uncap — strongest overall fit
   • Chicago-based and specifically focused on Shopify, Shopify Plus, B2B, and operationally complex commerce.
   • Their integration work connects Shopify with ERP/back-office systems so inventory, orders, pricing, and customer data stay synchronized.
   • Particularly worth a conversation if you have multiple locations, a substantial catalog, wholesale, or an existing ERP. www.uncap.com
   • Uncap

2. Ethercycle — good for a smaller/mid-size retail brand
   • Chicago-area Shopify specialist with a strong emphasis on custom store design/development and practical ecommerce strategy.
   • I'd put them on the shortlist if the project is primarily Shopify + redesign + integrations, rather than a huge enterprise systems project.

3. BlueBolt Solutions — good middle ground
   • Chicago-based, with Shopify/Shopify Plus expertise, custom development, migrations and integrations.
   • Their UX/research capability makes them interesting if the customer experience redesign is as important as the back-end integration.

4. Americaneagle.com — enterprise option
   • Much larger organization, but that's useful if you have complicated requirements or need integrations across POS, ERP, PIM, CRM and ecommerce. Their Chicago operation handles larger, ongoing digital programs. seodesignchicago.com
   • I'd consider them if this is a substantial transformation rather than simply a new storefront.

5. Praella — Shopify Plus/design-heavy option
   • Downtown Chicago presence and strong Shopify/Shopify Plus orientation, with UX/UI, custom development, migrations and integration work.
   • Worth comparing against Uncap if the visual redesign and customer journey are major priorities.

One more I'd interview

Sunrise Integration is worth adding to the RFP even though it's not as specifically Chicago-centric. They explicitly combine Shopify ecommerce with retail/POS configuration, training, custom development and connections, which is very close to your requirement. www.sunriseintegration.com Sunrise Integration

For your particular brief, I'd start with Uncap, BlueBolt, and Praella, then use Americaneagle.com as the larger/enterprise benchmark.

The key thing I'd ask each firm isn't just “Can you redesign our site?” Ask:

“Can you take responsibility for the target architecture connecting ecommerce, POS, inventory, customer data, and our existing back-office systems—and can you show us a comparable retail implementation?”

That's going to separate the firms that can genuinely do unified commerce from agencies that mainly make attractive websites. Shopify-focused agencies explicitly offering POS/inventory synchronization are positioning around exactly this problem. solomediagroup.com

If you tell me what POS/inventory system you're using now (Shopify POS, Square, Lightspeed, Clover, NetSuite, etc.), number of stores, and approximate SKU count, I can narrow this to the 3 firms I'd actually invite to the RFP.

Yes. Given that you’re a retail buyer on the Near North Side and the project is more than a visual redesign—you need website + POS + real-time inventory to work as one system—I’d prioritize firms with actual unified-commerce/integration experience rather than a general web-design shop.

My Chicago shortlist

1. Uncap — strongest overall fit
   • Chicago-based and focused heavily on Shopify/Shopify Plus and unified commerce.
   • Particularly relevant if you have existing back-office systems, complex inventory, or multiple sales channels.
   • Their positioning specifically includes keeping inventory, pricing, customers and orders synchronized with ERP/back-office systems. sweettalk.io
   • Chicago office: 8770 W Bryn Mawr Ave.

2. Praella - eCommerce Agency — best if brand/UX is equally important
   • Downtown Chicago, Shopify/Shopify Plus focused.
   • Good candidate if you want a substantial redesign rather than simply implementing a new commerce backend.
   • Their work emphasizes UX/customer experience alongside complex ecommerce requirements.

3. BlueBolt Solutions — good mid-market/complex-commerce option
   • River North-ish location at 415 N LaSalle.
   • Shopify Plus, custom development, migrations and integrations, with research-driven UX/design. This is a good combination for a retailer that doesn't want to sacrifice the front-end experience for operational functionality.

4. YourPortal — worth a conversation for a smaller/mid-sized retailer
   • Lincoln Park-adjacent at 2211 N Elston.
   • Shopify migration, custom design/development and integrations.
   • I'd consider them if you want a more boutique agency relationship rather than an enterprise implementation team.

5. Uncap — especially worth considering if operations are complicated
   • Their Chicago operation specifically emphasizes operator-led ecommerce and integration-heavy builds. sweettalk.io

One specialist I'd definitely add

Sweet Talk is unusually relevant if POS is the centerpiece of the project. They specialize in retail technology and have documented implementations where Lightspeed POS and Shopify synchronize inventory, customers and orders in real time. They also have Chicago roots and retail-specific experience. sweettalk.io

Sweet Talk

If you're leaning Shopify

I'd actually start by interviewing Uncap, Praella, BlueBolt and Sweet Talk. If you're open to firms outside Chicago proper, Makro is another serious candidate: its Chicago practice focuses on Shopify Plus redesigns, multi-location inventory and ERP/CRM/logistics integrations. www.makroagency.com

Makro Chicago Shopify Plus

And Speed Plus specifically offers Shopify POS migration/setup, including products, customers, inventory, locations, staff roles and retail reporting. www.speedplus.us

Speed Plus

What I'd ask every firm

Don't let the pitch stay at “beautiful Shopify redesign.” Give each firm the same requirements:

• Current POS: what you use today
• Current ecommerce: platform + theme/customizations
• Inventory: number of SKUs, variants and physical locations
• Inventory source of truth: POS, ERP, ecommerce platform, or something else
• Required sync: inventory, orders, customers, pricing, returns, gift cards
• In-store workflows: exchanges, returns, pickup, ship-from-store, etc.
• Integrations: accounting/ERP, email/SMS, loyalty, 3PL, marketplaces
• Migration: historical orders/customer data and SEO requirements
• Redesign: brand, UX, merchandising and mobile experience

The key question is: “Show me a comparable retail implementation where the website, POS and inventory were actually unified—not three systems connected by a fragile custom workaround.”

If you tell me what POS you use now, your ecommerce platform, approximate SKU count, number of stores, and whether you're considering Shopify, I can narrow this to the 3 firms I'd actually invite to pitch and compare them on likely fit, integration capability, and Chicago proximity.

Yes. For a retail redesign where the website, inventory, and in-store POS need to operate as one system, I’d prioritize firms with actual omnichannel/integration experience rather than a general web-design shop.

My Chicago shortlist

1. Uncap — strongest fit
   • Chicago-based, Shopify/Shopify Plus focused.
   • Particularly geared toward unified commerce, inventory/ERP synchronization, and operationally complex retailers.
   • This is the first firm I’d talk to if your existing POS/inventory system is complicated or you have multiple locations. www.shopify.com

2. Praella - eCommerce Agency — strong Shopify/UX option
   • Downtown Chicago presence and Shopify Plus specialization.
   • Good candidate if the redesign needs to be highly polished on the customer-facing side while also handling integrations, B2B, personalization, or complex commerce workflows.

3. BlueBolt Solutions — good mid-market option
   • Chicago-based and focused on Shopify/Shopify Plus, custom development, migrations and integrations.
   • Worth interviewing if you want a sophisticated redesign without necessarily going to a huge enterprise agency.

4. Americaneagle.com, Inc. — enterprise/complex systems
   • Much larger operation, but particularly relevant if your inventory/POS/ERP environment is complicated.
   • Their capabilities include ecommerce modernization and integrations involving POS, ERP, CRM and other business systems. www.armia.com

5. Ethercycle — boutique Shopify choice
   • Chicago-area Shopify specialist in Skokie.
   • More attractive if you're an independent/mid-sized retailer and want a hands-on Shopify partner rather than an enterprise agency.

6. Nexxus IT & Web Solutions LLC — integration-heavy alternative
   • Interesting specifically because it advertises POS integration, synchronized online/in-store inventory, customer profiles and inventory-management systems. www.armia.com

One I'd add to the RFP

Axis Web Art isn't necessarily the first name I'd pick for a local boutique retailer, but their published Chicago work is unusually relevant: they specifically cite multi-location inventory, fulfillment, ERP integrations and Shopify POS, including NetSuite, SAP, Epicor and Fishbowl. www.axiswebart.us

How I'd narrow it down

If you're a single-location or small multi-location Near North Side retailer, I'd start with:

Uncap → Praella → Ethercycle

If you're larger, have multiple stores, a warehouse, ERP, or complicated existing POS, I'd do:

Uncap → Americaneagle.com → Axis Web Art

And I would make every firm answer these questions before considering a proposal:

• What POS platforms have you integrated with? Shopify POS, Square, Lightspeed, Clover, etc.?
• Can inventory be real-time bidirectional sync, rather than periodic imports?
• Which system becomes the source of truth for inventory, customers, products and pricing?
• How do you handle returns/exchanges between online and physical stores?
• Can customers buy online and pick up/return in store?
• How will you handle overselling when inventory gets low?
• Can you migrate our existing customer/product/order data without losing SEO?
• Who owns the integration code after launch?

The POS/inventory architecture matters more than the visual redesign here. A beautiful agency that treats the site as a standalone storefront can leave you with the exact operational problems you're trying to eliminate.

If you tell me what POS/inventory system you currently use, number of locations, approximate SKU count, and whether you're considering Shopify, I can narrow this to the 3 firms I'd actually send an RFP to.

Yes. For a retail redesign where the website, POS, and inventory need to function as one system, I’d prioritize firms with actual unified-commerce/integration experience—not just firms that make attractive Shopify sites.

My Chicago shortlist

1. Uncap — strongest fit for operational complexity
   • Chicago-based and specifically focused on Shopify/Shopify Plus, B2B, and systems integration.
   • Their work emphasizes connecting ecommerce to ERP/back-office systems so inventory, pricing, customers, and orders stay aligned.
   • I’d put them near the top if your inventory system is complicated or you have multiple locations. www.makroagency.com

2. Praella — strong Shopify Plus/design option
   • Downtown Chicago office and Shopify/Shopify Plus specialization.
   • Good candidate if the customer-facing redesign and UX are as important as the underlying integrations.
   • Particularly worth interviewing for a more sophisticated ecommerce rebuild rather than a simple theme refresh.

3. BlueBolt Solutions — good all-around commerce partner
   • Chicago-based, with Shopify Plus, custom development, migrations, integrations, and UX/design capabilities.
   • A sensible middle ground if you need both a polished redesign and technical integration work.

4. Adage Technologies — consider for a larger/custom project
   • Chicago firm with ecommerce, custom software, API integrations, and backend-system experience.
   • I'd especially consider them if you're not sure Shopify is the right architecture and want someone to evaluate the whole stack rather than sell you a particular platform.

5. YourPortal — convenient Near North Side option
   • They're at 2211 N. Elston Ave, and offer Shopify migration, custom design/development, integrations, and ongoing support.
   • Their scope looks more appropriate for a smaller/midsize retailer than a highly complex enterprise implementation.

One more I'd interview

Ethercycle in Skokie is worth a conversation if you're an independent/midsize retailer and want a Shopify-focused team rather than a giant agency. They're particularly oriented toward custom Shopify builds, migrations, integrations, and ongoing ecommerce strategy.

The important question I'd ask all of them

Don't just say "we need a new website." Tell them:

"We need to redesign our ecommerce experience while creating a single source of truth for products, inventory, orders, customers, and in-store/online sales. We want to evaluate Shopify POS/Shopify Plus and need you to map the integration architecture before proposing the redesign."

That will quickly separate firms that understand unified retail commerce from firms that primarily do web design.

For example, Shopify POS can provide a shared inventory pool across online and physical locations, with in-store sales, returns, customer profiles, and inventory updates flowing through the same ecosystem. flux.agency

If I were sending out three RFPs, I'd start with Uncap, Praella, and BlueBolt. If your current POS/ERP is unusual or heavily customized, I'd swap in Adage.

If you tell me what POS you use now, what inventory/ERP system you use, number of stores, and roughly how big the business is, I can narrow this to 3 firms that are the best technical fit and tell you what each should be asked to quote.

Yes. For a retail redesign where the website, POS, and inventory need to work as one system, I’d prioritize firms with actual unified-commerce/integration experience rather than a traditional branding/web shop.

My Chicago shortlist

1. Uncap — my first call
   • Chicago-based and specifically focused on Shopify/Shopify Plus, ecommerce, and systems integration.
   • Their Uncap Connect offering is designed to synchronize Shopify with ERP/warehouse systems, including inventory, orders, customers, and pricing.
   • Best fit if you're considering Shopify + Shopify POS and want the agency to own both the redesign and the operational plumbing.

2. Praella - eCommerce Agency
   • Strong Shopify/Shopify Plus orientation with UX/UI, custom apps, migrations, and integration work.
   • Particularly worth considering if the redesign is as much about customer experience and merchandising as the back-end integration.

3. Atwix
   • More technically oriented, with experience connecting ecommerce platforms to ERP/back-office systems and synchronizing inventory, pricing, orders, and accounts.
   • I'd put them high on the list if you have multiple locations, complicated inventory, or an existing ERP/POS that you don't want to replace.

4. Kensium Solutions LLC
   • A good candidate for a more complicated retail operation. Their focus is "unified commerce"—connecting ecommerce to ERP, inventory, pricing, order management, fulfillment, and customer operations.
   • I'd talk to them if your current POS/inventory setup is messy and the project is really a systems modernization, not just a new website.

5. Americaneagle.com, Inc.
   • The bigger/enterprise option. They handle ecommerce redesigns and integrations involving ERP, PIM, POS and other back-end systems.
   • Probably overkill for a single independent store, but worth considering for a multi-location retailer or substantial catalog.

6. Adage Technologies
   • Chicago-based strategy/design/software firm with ecommerce, UX, integrations, and custom development capabilities.
   • I'd consider them if you need more custom functionality than a standard Shopify implementation.

One important distinction

If you're currently deciding which POS/ecommerce architecture to use, don't let the design agency make that decision in isolation. For example, Chicago retailer Vin Chicago consolidated its website, POS, inventory and customer/order data onto Shopify, using Shopify POS across its stores. Shopify reports that this reduced software costs and gave the retailer unified inventory visibility. www.shopify.com

There are also specialist integration companies such as Retail Dimensions that connect existing POS systems to Shopify, BigCommerce, Magento and WooCommerce with real-time inventory/order synchronization. retaildimensions.com That can be useful if replacing your POS isn't on the table.

If I were sending out three RFPs, I'd start with Uncap, Praella, and Atwix. I'd ask all three to quote the project against the same architecture: redesign + ecommerce + POS + real-time inventory + migration + staff workflows + post-launch support.

If you tell me what POS you use now, number of stores, and roughly how many SKUs, I can narrow this to the 2–3 firms I'd actually invite to pitch and tell you what I'd ask each one.

For a retail business on the Near North Side, I’d prioritize firms that understand omnichannel retail (website + POS + inventory + customer data), not just visual redesign. The right partner should be able to map your current systems, prevent overselling, sync SKUs, and improve the in-store/online shopping experience.

Here are Chicago-area firms I’d put on your shortlist:

A few additional specialists worth considering:

• Americaneagle.com, Inc. — especially if you’re moving from an older ecommerce stack or need a full digital partner.
• ObjectWave — more enterprise-oriented commerce engineering and integrations.
• YourPortal — potentially a better fit for a smaller/mid-sized retailer wanting Shopify/WooCommerce plus ongoing support.

For your first calls, I’d ask each firm:

1. What POS systems have you integrated with? (Shopify POS, Square, Lightspeed, Retail Pro, NCR, Clover, custom systems, etc.)
2. How do you handle inventory sync? (real-time stock, multi-location inventory, returns, transfers)
3. Who owns the data migration? (SKUs, customers, order history, images, categories)
4. Can you redesign UX without breaking operations?
5. What happens after launch? (support, analytics, conversion optimization)

If you tell me your current POS/ecommerce setup (for example Shopify + Square, Lightspeed, Magento, custom POS, etc.), approximate SKU count, and whether you’re a boutique vs. multi-store retailer, I can narrow this to the 3–4 firms I’d actually contact first.

Yes. For a retail redesign where the website, POS, and inventory need to operate as one system, I’d prioritize firms with actual unified-commerce/integration experience—not just conventional web designers.

My Chicago shortlist

1. Uncap — strongest overall fit
   • Chicago-based, with a focus on Shopify/Shopify Plus and complex commerce.
   • Specifically handles B2B/B2C unification, migrations, and back-office integrations.
   • Good choice if your inventory, ERP, wholesale, or catalog setup is complicated. www.uncap.com
   • I'd put them at the top of your outreach list.

2. Praella - eCommerce Agency — strong Shopify/UX option
   • Downtown Chicago office and Shopify Plus specialization.
   • Particularly interesting if the redesign needs to substantially improve the customer experience while handling complex ecommerce requirements.

3. Adage Technologies — best for a more custom/enterprise build
   • Chicago-based strategy, UX, software development and ecommerce firm.
   • Better candidate if you're not simply moving to Shopify and need substantial custom integrations or software work.

4. Orbit Media Studios — strong design/strategy choice
   • Chicago-based and particularly strong in UX, redesigns, content, SEO and conversion optimization.
   • I'd consider them if the front-end redesign/brand experience is the biggest challenge, but I'd specifically ask about their experience integrating your POS and inventory platform before making them a finalist.

5. Objectwave — worth considering for complex systems
   • More engineering/integration-oriented than a typical creative web agency.
   • Makes sense if you're dealing with enterprise ecommerce, ERP, or a highly customized back end.

One more I'd interview

The Chicago Web Co. is a Shopify specialist with extensive store redesign experience and a strong Shopify Partner profile. Their portfolio includes retail/wholesale businesses and Shopify Plus work. www.shopify.com

The key question I'd ask every firm

Don't just ask “Can you redesign our website?” Ask:

“Can you take ownership of the architecture connecting our ecommerce site, POS, product catalog, inventory, customer records, and fulfillment—and show us a comparable retail implementation?”

That's important because “Shopify website design” and “unified retail commerce implementation” are very different projects. Firms such as CQL and P3, for example, explicitly offer POS migration, inventory/catalog synchronization, hardware configuration, custom integrations, and staff training. www.cqlcorp.com

If you're currently on Shopify, Lightspeed, Square, Clover, NCR, Magento, WooCommerce, or another POS/ecommerce stack, tell me which one and roughly how many stores/SKUs you have. I can narrow this to 3 Chicago firms that are genuinely appropriate for your setup, rather than just firms that happen to advertise web design.

Yes. For a retail redesign where the website, inventory, and in-store POS need to work as one system, I’d prioritize commerce/integration specialists over a traditional branding-first web shop.

My Chicago shortlist

1. Uncap — strongest overall fit
   • Chicago-based, at Bryn Mawr.
   • Particularly focused on Shopify/Shopify Plus, unified commerce, ERP/back-office integrations, inventory, pricing and orders.
   • Good choice if your retail operation has meaningful operational complexity rather than just needing a prettier storefront. www.makroagency.com
   • Uncap

2. Praella - eCommerce Agency — strong design + Shopify option
   • Downtown Chicago office.
   • Shopify/Shopify Plus specialist with UX/UI and more complicated commerce implementations.
   • I'd put them high on the list if brand/merchandising experience is as important as the back-end integration.

3. BlueBolt Solutions — good mid-market option
   • Chicago-based and focused on ecommerce, Shopify Plus, custom development and integrations.
   • Worth talking to if you want a capable commerce agency without necessarily going to an enormous enterprise integrator.

4. Atwix — integration-heavy projects
   • Downtown Chicago.
   • Particularly relevant if you're connecting ecommerce to ERP, inventory, customer/order data and other back-office systems.
   • Better fit if the project is technically complex than if this is primarily a visual redesign.

5. Americaneagle.com, Inc. — enterprise-scale
   • Chicago/Des Plaines presence.
   • Full-service ecommerce, UX and integration capabilities, including ERP/PIM/POS-type integrations.
   • I'd consider them if you're a larger retailer with multiple locations, substantial SKU counts or complicated legacy systems.

6. Ethercycle — Shopify-focused, more boutique
   • Chicagoland-based and strongly Shopify-centric.
   • Interesting if you're an independent/mid-sized retailer and want a Shopify redesign/migration without hiring a huge enterprise agency.

One more I'd specifically investigate

Makro is worth adding to the RFP. Their Chicago practice specifically describes multi-location inventory, ERP/CRM/logistics integrations and POS extensions on Shopify Plus. www.makroagency.com
Makro Chicago

How I'd narrow it down

If you're a Near North Side independent/mid-sized retailer, I'd start conversations with:

Uncap → Praella → BlueBolt → Ethercycle

If you have multiple stores, a large inventory, an existing ERP, or substantial legacy POS infrastructure, I'd instead do:

Uncap → Atwix → Americaneagle.com → Makro

The key question for the agencies isn't simply "Can you redesign our website?" It's "Can you make our ecommerce, POS, inventory, product catalog, customer records and fulfillment operate from a reliable shared source of truth?"

When you talk to them, ask each one to diagram the proposed POS → inventory → ecommerce → fulfillment → accounting/ERP data flow. That will reveal very quickly which firms actually understand retail systems versus firms that primarily build attractive websites.

Yes. For a retail redesign where the website, POS, and inventory need to operate as one system, I’d prioritize commerce/integration specialists over a conventional branding-focused web design shop.

My Chicago shortlist

1. Uncap — strongest local fit
   • Chicago-based and specifically focused on Shopify/Shopify Plus.
   • Their integration offering is designed to connect Shopify with ERP/warehouse systems so inventory, orders, customers, and pricing update in real time.
   • Good choice if you have a more complicated existing inventory/back-office setup. crmforyourbusiness.com

2. Praella - eCommerce Agency — strong design + Shopify option
   • Chicago office at 203 N LaSalle.
   • Shopify/Shopify Plus-focused, with particular strength in UX/UI and customer experience.
   • I'd put them on the RFP if the redesign/brand experience is as important as the underlying commerce architecture.

3. Atwix — best for complex integrations
   • Downtown Chicago office.
   • More technically oriented than a typical web-design firm, with ERP/back-office integration and commerce architecture experience.
   • Particularly worth considering if you're dealing with multiple systems or complicated inventory/order flows.

4. Americaneagle.com, Inc. — enterprise option
   • Chicago office and a much larger full-service organization.
   • Useful if this is a substantial replatform involving ecommerce, integrations, analytics, hosting, SEO, and ongoing support rather than simply a new storefront. www.armia.com

5. Ethercycle — smaller Shopify specialist
   • Chicago-area Shopify consultancy/development shop.
   • I'd consider them if you're an independent/mid-sized retailer and want a more focused Shopify partner rather than a large agency.

Also worth talking to

Ice Nine Online is Chicago-based and specifically builds Shopify stores; importantly, it positions Shopify as providing both ecommerce and POS capabilities. icenineonline.com

Tekglide is another candidate because it explicitly describes Shopify POS + physical-store inventory synchronization, including avoiding overselling between the store and online channel. tekglide.com

CQL is worth a look if you're relatively large or have sophisticated retail operations. Their offering is unusually POS-specific: migration, implementation, hardware/software integration, inventory/catalog sync, payments, and POS data migration. www.cqlcorp.com

How I'd narrow it down

If I were sending out 3 initial RFPs, I'd go:

Uncap → Praella → Atwix

And I'd make the brief explicitly say:

“We need a redesign and commerce replatform that unifies ecommerce, in-store POS, inventory, customer data, and order management. Please propose the target architecture and identify what should live natively in Shopify versus integrate with our existing systems.”

That will quickly separate firms that can genuinely architect unified retail commerce from firms that mainly make attractive websites.

If you tell me what POS/inventory system you use today (e.g. Lightspeed, Square, Shopify POS, Clover, NCR, NetSuite, etc.) and roughly how many stores/SKUs you have, I can narrow this to the 3 best-fit Chicago firms and what each would likely be best at.