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Black Friday Is Four Weeks Away. The Holiday Website Checklist for Small Businesses

Nathan Strickland

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business glass

Black Friday is November 27 and Cyber Monday is November 30. If your website needs work before the holidays, the window to do it safely is closing. Most stores lock down changes the week before Thanksgiving.

What the forecasts say

  • Online holiday sales up about 8%. Practical Ecommerce projects U.S. online sales from Nov. 1 to Dec. 31 to rise around 8% from last year, when Adobe tracked $257.8 billion.
  • AI is sending real buyers. Shoppers who arrive from generative AI tools converted 31% better than other visitors last holiday season, according to Adobe, and the forecast is at least 25% better this year.
  • Buy now, pay later keeps growing. BNPL is projected to finance more than $22 billion in U.S. online holiday purchases.

The four-week checklist

  1. Week 1: speed and mobile. Test your key pages on a phone over cellular data. Compress large images, remove unused plugins and fix anything that takes more than a few seconds to load.
  2. Week 2: be easy for AI to read. Clear product names, honest descriptions, prices, shipping cutoffs and return policies in plain text, not just in images. Add an FAQ that answers the questions customers actually ask. This is what AI assistants pull from when they recommend a store.
  3. Week 3: checkout. Run a real test order. Offer the payment options your customers expect, including a pay-over-time option if your processor supports it, and make sure confirmation emails arrive.
  4. Week 4: freeze and back up. Take a full backup, stop making major changes, and post your holiday hours and shipping deadlines on the homepage.

Don’t forget security

Holiday traffic attracts bots and card-testing attacks. Update WordPress, your theme and plugins now, before the freeze. And remember that PHP 8.2 loses security support on December 31, so plan that upgrade for the quiet week after the holidays.

Want a second set of eyes? Fenway Web will run a free holiday-readiness check on your site, covering speed, mobile, checkout and security, and send you a prioritized fix list. Request a check →

Sources: Practical Ecommerce. Written by the Ecosystem Intelligence Desk.

The post Black Friday Is Four Weeks Away. The Holiday Website Checklist for Small Businesses appeared first on Fenway Web.

Founder & Chairman of Boston Made, Inc., a Boston-based media and business portfolio company. I lead Boston Made's independent, hyperlocal coverage of Boston's economy, businesses, and neighborhoods, alongside a growing portfolio of Boston-rooted brands — including Boston Made Pets, where my passion for dog wearables and canine wellness lives on. I’m an avid reader and journaler who believes in reporting that's closer to home.

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Five Native Apps, One Studio: How We Built the App Family

Nathan Strickland

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Five Native Apps, One Studio: How We Built the App Family

This week we shipped the biggest project in Fenway Web’s history: five native apps for iPhone, iPad and Apple Watch, built for five very different brands. They are Boston Made, Paxton, GrandStrand, Spot Check and BOSSTOX. Here is how we approached it, and what it means if you are thinking about an app of your own.

One foundation, five personalities

Each brand already had a strong website, so the first rule was that every app had to look and feel like its site. A reader moving between the GrandStrand website and the GrandStrand app should never feel a seam. Under the hood, the five apps share a single Swift foundation for feeds, offline saving, article rendering and layout. On top of that, each app gets its own colors, typography, navigation and native features.

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That shared core is why we could build five apps at once without cutting corners. A fix or improvement to the reader, the image pipeline or the offline cache lands in all five at the same time.

Native where it counts

  • iPhone: fast native feeds, a clean reader view and saved stories that work offline.
  • iPad: real iPad layouts, not stretched phone screens. Magazine grids for Boston Made, side-by-side research for Paxton and big maps for Spot Check and GrandStrand.
  • Apple Watch: a companion app for every brand, from GrandStrand’s Coast Now weather and tides to BOSSTOX research at a glance.
  • Privacy: none of the five apps collects personal data. There are no accounts, no tracking and nothing to sign up for.

Submitted to the App Store · Launching soon

Five apps. Every screen.

Real screens from the Boston Made app family, on iPhone, iPad, Apple Watch and the iPhone Duo.

Coming soon

Built for iPhone Duo.

Every app in the family is coming to Apple’s new foldable. Open it, and each app spreads into a two-pane layout: the feed on one side, the story on the other.

Version 1.0 · Submitted to the App Store · Launching soon

The five apps

Real screenshots from every app on iPhone, iPad and Apple Watch.

Boston Made

The whole Boston Made family in one calm feed.

Today’s stories from across the network, saved for offline reading, with a shop of thousands of products on the way.

  • iPhone
  • iPad
  • Apple Watch
  • Free

Get Boston Made

Boston Made on iPhone
Boston Made on iPhone
Boston Made on iPhone
Boston Made on iPad
Boston Made on Apple Watch

Paxton

Healthcare insight, analyzed.

Healthcare deals, markets and policy in plain English, with a healthcare marketplace on the way.

  • iPhone
  • iPad
  • Apple Watch
  • Free

Get Paxton

Paxton on iPhone
Paxton on iPhone
Paxton on iPhone
Paxton on iPad
Paxton on Apple Watch

BOSSTOX

Markets and the AI build-out.

Live market quotes, plain-English BOSSTOX research and headlines, with in-app stock trading on the way.

  • iPhone
  • iPad
  • Apple Watch
  • Free

Get BOSSTOX

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BOSSTOX on iPhone
BOSSTOX on iPhone
BOSSTOX on iPhone
BOSSTOX on iPad
BOSSTOX on Apple Watch

GrandStrand

The coast, connected.

Live Myrtle Beach weather and tides, a map of the whole Grand Strand and what’s happening today, with local restaurants, venues and real-estate partners joining soon.

  • iPhone
  • iPad
  • Apple Watch
  • Free

Get GrandStrand

GrandStrand on iPhone
GrandStrand on iPhone
GrandStrand on iPhone
GrandStrand on iPad
GrandStrand on Apple Watch

Spot Check

Every spot has a story.

Parking near you, local parking guides and saved spots, with thousands of LAZ Parking spaces coming to the app.

  • iPhone
  • iPad
  • Apple Watch
  • Free

Get Spot Check

Spot Check on iPhone
Spot Check on iPhone
Spot Check on iPad
Spot Check on Apple Watch

Built to grow

A launch is a starting line. The apps are built to take on new features: a healthcare marketplace in Paxton, in-app trading in BOSSTOX, thousands of LAZ Parking spaces in Spot Check, a shop in Boston Made and local partners in GrandStrand. Lumo and PUPWEAR® are next on our bench.

Thinking about an app?

If your business has a website people love, it can have an app people keep. We design and build native apps for iPhone, iPad and Apple Watch that match your brand, and we stay on to maintain them. Talk to us about an app.

The post Five Native Apps, One Studio: How We Built the App Family appeared first on Fenway Web.

Boston Made Reader Boston Made family Boston Made Reader Free e-reader app for long reads, wires and books. Visit site →

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WordPress 7.0 Put AI in Your Dashboard. What Small Businesses Should Actually Turn On.

Nathan Strickland

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tech servers

WordPress 7.0, codenamed “Armstrong,” shipped on May 20, 2026. It is the first release to build AI directly into the core software, and the first full admin redesign since 2013. Five months on, here is a practical read for business owners.

What changed

  • AI connectors (opt-in). A new Settings → Connectors screen links your site to AI providers, with Anthropic, Google and OpenAI as defaults. Nothing turns on unless you enable it.
  • A new admin. A modern color scheme, a command palette for jumping anywhere in the dashboard, and a Fonts screen under Appearance.
  • Visual Revisions. Compare saved versions of a page side by side before you restore one.
  • Better Notes. Email notifications for mentions and a suggestions mode, useful when an agency and a client edit together.
  • New blocks. Breadcrumbs, Icon and a gallery lightbox, plus showing or hiding blocks by device.

What got cut

Real-time co-editing, the most hyped feature, was pulled 12 days before launch over stability concerns. Tabs, slider and table-of-contents blocks also missed the release.

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Our recommendations

  1. Turn on: Visual Revisions and breadcrumbs. Breadcrumbs help visitors and search engines understand your site.
  2. Try carefully: AI drafting for product descriptions or image alt text. Always have a person review it, since copy that sounds like everyone else won’t help you stand out in search.
  3. Leave off for now: giving AI tools broad permission to publish or change settings without review.
  4. Check first: 7.0 needs a newer server, and PHP 8.2 loses security support on Dec. 31, so plan that upgrade alongside it.

Not sure what your site runs on? Fenway Web will check your server version, plugins and backups for free and tell you exactly what needs to change. Request a site check →

Sources: DreamHost · WordPress Make Core. Written by the Ecosystem Intelligence Desk.

The post WordPress 7.0 Put AI in Your Dashboard. What Small Businesses Should Actually Turn On. appeared first on Fenway Web.

Boston Made Foundation Boston Made family Boston Made Foundation The philanthropic arm of the Boston Made family. Visit site →

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Building a Store FAQ Page That Cuts Down Support Emails

Nathan Strickland

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on

The lit marquee of a restored historic movie palace

Every online store hears the same questions again and again. When will my order ship? Do you offer gift wrapping? Can I change my order? A good FAQ page answers those questions once, clearly, in a place customers can find. It saves your team time and gives shoppers confidence, especially during the busy season when inboxes fill quickly.

Start with real questions

The best FAQ pages are built from the questions customers actually ask, not the ones a business imagines. Gather them from:

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  • Your email inbox and contact form submissions.
  • Chat transcripts, if you offer live chat.
  • Phone calls and in-store conversations, as remembered by staff.
  • Comments and messages on social media.
  • Product reviews, which often reveal confusion.

Keep a running list for a few weeks and note how often each question comes up. The most frequent ones belong at the top.

Organize by topic

A long, unsorted list of questions is hard to scan. Group questions into clear categories, such as:

  • Orders: changing or canceling an order, order status, payment methods.
  • Shipping: processing times, costs, destinations, tracking.
  • Returns and exchanges: eligibility, process, refund timing.
  • Products: sizing, materials, care, availability.
  • Gifts: gift cards, wrapping, sending directly to a recipient.
  • Accounts: creating an account, resetting a password.

On longer pages, a short list of category links at the top helps people jump to the right section. Expandable question-and-answer sections can keep the page compact, as long as they work with a keyboard and screen readers and the text remains searchable.

Write short, direct answers

Each answer should lead with the direct response, then add detail. If the answer to whether you ship internationally is yes, to certain countries, say that in the first sentence. Use the same plain language as your customers. Avoid hedging and legal phrasing unless it is genuinely needed.

When a full policy exists, such as returns or shipping, give a concise answer and link to the policy page for details. Make sure the FAQ and the policy pages say the same thing. Contradictions create more questions, not fewer.

Put answers where questions arise

An FAQ page works best as part of a broader approach. Link to it from the footer, the contact page and order confirmation emails. Repeat the most relevant answers where people are deciding, such as sizing notes on product pages and shipping details in the cart. The goal is to answer questions at the moment they occur.

Keep it current

FAQ pages go stale as policies, products and seasons change. Review the page before busy periods, add seasonal answers such as holiday shipping cutoffs and remove them afterward. When a new question starts arriving repeatedly, add it. Always include a clear way to contact a real person for anything the page does not cover. An FAQ should make help easier to find, never harder.

The post Building a Store FAQ Page That Cuts Down Support Emails appeared first on Fenway Web.

Boston Made UK Boston Made family Boston Made UK Boston Made across the Atlantic. Visit site →

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