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Generated Oct 21, 2026
  1. Programmable
  2. Playbooks
  3. Dana Cooper Designs
Dana Cooper Designs logo

growth playbook · Oct 21, 2026

danacooper.net (opens in a new tab)

Dana Cooper Designs growth playbook

Diagnosis

Dana Cooper has the credentials most small resortwear brands lack: British Vogue and Tatler features, an America's Cup licence, Saks and resort stockists, and two decades of original artwork. The shop under-uses them.

Overseas visitors are told it ships only to the US, the shipping page names another brand, most cashmere is sold out, product data is messy, there are no reviews, the blog stopped in 2023 and the phone page jumps. This playbook fixes those first, then grows the higher-value work: wedding scarves and planners, regatta and corporate commissions, wholesale, prints and licensing.

Growth Score

5/10

Biggest Opportunity

Turn the artwork and the custom-design credentials into repeatable products and channels: wedding party scarves, club and corporate collections, wholesale and licensing, alongside an online shop that serves visitors from abroad.

Biggest Risk

A one-artist studio has limited time. Competing on online resortwear alone against Lilly Pulitzer, Roller Rabbit and Vilebrequin, with free shipping and returns, will not pay; the time has to go where Dana's originality earns most.

01

Start here

The three moves to make first. Each one is written up in full below.

  1. 1

    Tell overseas shoppers you ship to them, and fix the shipping page that names another brand

    Edit the announcement bar and the shipping policy today.

    High impact First result in 2 weeks
  2. 2

    Bring back the sold-out cashmere scarves, with a waitlist that captures demand now

    Add the back-in-stock form to the five sold-out scarves.

    High impact First result in 1 month
  3. 3

    Give the $3,000 wedding packages their own enquiry form

    Write the six questions and the automatic reply.

    High impact First result in 1 month

02

Your idea portfolio

21 ideas, grouped by when to run them. Open any idea for how to run it: the steps, who to approach, copy you can use, and how to measure it.

  • 7 ideas are marked Unexpected: plays you are unlikely to have tried.

Every idea placed by the effort it takes against the impact it could have. Quick wins sit top left; select a number to open that idea. The filters below narrow the list by status, timing, category and what Programmable can build.

Effort vs impactEach number is an idea. Select one to open it.
Impact →
Quick wins · 3Big bets · 8Fill-ins · 10Reconsider · 0
Effort →

Showing 21 of 21 ideas

This week 6

Quick wins with a clear first action.

  • 01

    The first line on every page says "Shipping available for US-based orders", yet the shipping policy says orders go to "most countries", duty-paid with Passport, in 8–14 business days. The same policy tells customers to track parcels on "your India/Julia Amory tracking page", a leftover from another brand. Visitors from the UK, Canada and the Caribbean (where British Vogue, Tatler and past stockists send them) are told they cannot buy.

    High impactLow effort First result in 2 weeks Founder and Creative Director

    First action

    Edit the announcement bar and the shipping policy today.

    How to measure it

    International orders

    Now
    –
    Target
    +50%
    By
    90 days

    Steps

    1. 1

      Rewrite the bar

      Worldwide, duties included, Bermuda pick-up.

      Founder and Creative Director 30 minutes

    2. 2

      Fix the policy

      Remove "India/Julia Amory"; add real tracking steps.

      Founder and Creative Director 1 hour

    3. 3

      Add delivery lines

      A product-page block with times by region.

      Shopify developer (freelance) 2 hours

    4. 4

      Check markets

      UK, Canada and EU currency and duties at checkout.

      Shopify developer (freelance) 2 hours

    5. 5

      Test an order

      One test checkout to the UK.

      Studio assistant 1 day

    6. 6

      Track

      Orders by country each month.

      Founder and Creative Director monthly

    First result
    2 weeks
    Cost
    $0
    Owner
    Founder and Creative Director

    Smallest test

    Change the bar today and watch international checkouts for a month.

    Why it works

    Change the bar to "Ships worldwide, duties included | Bermuda: local pick-up and drop-off", remove the other brand's name from the policy, and add a short delivery line on every product page (US, UK and EU, Caribbean, Canada). Check that Shopify Markets shows local currency for the UK and Canada pages already in the sitemap.

    Shoppers who think a store will not ship to them leave without trying checkout. Clear, duty-paid delivery is a real advantage for a small brand, and a clean policy page protects trust at the moment of purchase.

    Ready to use

    ChecklistShipping clean-up list

    [ ] Announcement bar: worldwide, duties included
    [ ] Bermuda pick-up and drop-off kept
    [ ] "India/Julia Amory" removed from the policy
    [ ] Delivery times on product pages by region
    [ ] UK and Canada currency checked at checkout
    [ ] One test order to the UK

    Risks and how to handle them

    • Canada orders still pay import fees

      Say so plainly on the Canada line.

    Evidence

    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
    • Your websiteShipping policy: "International shipping is currently available to most countries", sent Delivered Duty Paid with Passport and "typically delivered within 8 -14 business days" (Canada excluded from duty-paid shipping); it tells customers to track orders on "your India/Julia Amory tracking page".Source
    • DNS checkdanacooper.net uses Google Workspace mail and a Mailchimp newsletter; SPF is "~all" and the DMARC policy is "p=none", so the domain is not protected against spoofed email. The store runs on Shopify and the sitemap has English pages for Bermuda, Canada and the UK.Source
  • 02

    Five of the seven $275 Scottish cashmere scarves are sold out, including Pink Frangipani, the colour featured on the blog. Cashmere is the line Dana built "for the fall and winter" and for travel, and its product pages now end in a dead end.

    High impactLow effort First result in 1 month Founder and Creative Director

    First action

    Add the back-in-stock form to the five sold-out scarves.

    How to measure it

    Waitlist-to-order rate

    Now
    –
    Target
    20%
    By
    90 days

    Steps

    1. 1

      Install a back-in-stock app

      Email sign-up on sold-out variants.

      Shopify developer (freelance) 2 hours

    2. 2

      Add alternatives

      In-stock scarves and gloves on sold-out pages.

      Shopify developer (freelance) 2 hours

    3. 3

      Tell the list

      One newsletter about the waitlist.

      Founder and Creative Director 1 day

    4. 4

      Count sign-ups

      By colour, after two weeks.

      Studio assistant 2 weeks

    5. 5

      Reorder

      The top colours.

      Founder and Creative Director 1 month

    6. 6

      Email on restock

      Waitlist first, 24 hours before everyone.

      Founder and Creative Director on restock

    First result
    1 month
    Cost
    App fee and stock
    Owner
    Founder and Creative Director

    Smallest test

    Add the form to one scarf and count sign-ups for two weeks.

    Why it works

    Add a "notify me when back" form to every sold-out scarf, email the list when stock returns, and reorder the two or three colours with the most sign-ups. Until then, show the in-stock Bluebird and Freesia scarves and the $95 gloves on sold-out pages.

    A waitlist turns lost visits into a list of buyers and tells you which colours to reorder before committing cash.

    Risks and how to handle them

    • Mill lead times

      Tell sign-ups the expected date.

    Evidence

    • Your websiteCold-weather line: 100% Scottish cashmere scarves at $275 (launched December 2022, "for the fall and winter", per The Royal Gazette); five of the seven are sold out (Pink Frangipani, Limestone, Royal Navy Yacht, Allspice, Evening Black). Six fingerless gloves at $95 were added in December 2024 and two silk Bermuda scarves at $225 in late 2025.Source
    • Your websiteGift collections already in the shop: "Valentines Day Gifting" (cashmere and silk scarves, a $45 clutch), "Pre-order now for the holidays: the Bermuda scarf" (two $225 silk scarves), Bermuda journals at $18 and children's books.Source
    • Your websiteCatalogue (the store's public product feed, October 20, 2026): 84 products from $13 to $300, median $97.50: sarongs, swimwear, tunics, dresses, scarves, gloves, books and journals. The product type is blank or "0" on 23 products and spelled several ways elsewhere ("Swimwear", "bikini"; "beach tunic", "Beach Tunic", "tunics"; "Scarves", "cashmere scarves", "scarf"). Product pages show no customer reviews.Source
  • 03

    Wedding illustration packages start at $3,000 and are limited to a few couples a year, but every enquiry arrives through the same contact form as a scarf question (name, email, phone, comment). Dana has to email back for the date, place and budget before she knows whether the project fits.

    High impactLow effort First result in 1 month Founder and Creative Director

    First action

    Write the six questions and the automatic reply.

    How to measure it

    Wedding enquiries that book a call

    Now
    –
    Target
    50%
    By
    90 days

    Steps

    1. 1

      Write questions

      Date, venue, guests, pieces, budget, source.

      Founder and Creative Director 1 hour

    2. 2

      Build the form

      On the Weddings page.

      Shopify developer (freelance) 1 day

    3. 3

      Make the PDF

      Six projects and the process.

      Founder and Creative Director 1 day

    4. 4

      Set the reply

      Automatic email with booking link.

      Shopify developer (freelance) 2 hours

    5. 5

      Track

      Enquiries, calls and bookings.

      Studio assistant monthly

    6. 6

      Review

      Adjust the budget bands after ten enquiries.

      Founder and Creative Director quarterly

    First result
    1 month
    Cost
    $0
    Owner
    Founder and Creative Director

    Smallest test

    Put the form live and compare the next five enquiries.

    Why it works

    Add a wedding form: date, island or venue, guest count, pieces wanted (invitations, maps, scarves, decor), budget band from $3,000, and how they heard. Send an automatic reply with the process, a short portfolio PDF and a link to book a call.

    Couples planning a destination wedding compare several designers; a fast, professional first reply and early qualification win more of the right projects.

    Risks and how to handle them

    • Fewer enquiries

      Fewer, better ones save Dana's time.

    Evidence

    • Your websiteWeddings & Events page: custom invitations, maps, menus, place cards, bridal-party scarves, robes, ties and decor; "Custom wedding illustration packages start at $3,000. Projects are limited to a select number of couples each year"; clients receive print-ready files and "Original paintings are available to purchase". Testimonial from Cece Armstrong: Dana "designed a Bermuda scarf that highlighted venues from the wedding... we gave it as gifts to the wedding party". Enquiries go to a general contact form (name, email, phone, comment).Source
    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
  • 04

    Google's phone test measured a layout shift of 0.246 (good is under 0.1) caused by the British Vogue section, and the main banner image takes 4.8 s to appear. On a phone the page moves as it loads, so people tap the wrong thing, and touch targets were also flagged as too small.

    Medium impactLow effort First result in 1 week Shopify developer

    First action

    Set a fixed height on the Vogue section.

    How to measure it

    Layout shift on a phone

    Now
    –
    Target
    under 0.1
    By
    30 days

    Steps

    1. 1

      Fix the height

      Vogue section and banner.

      Shopify developer (freelance) 1 hour

    2. 2

      Resize the banner

      Phone-size modern image, high priority.

      Shopify developer (freelance) 2 hours

    3. 3

      Tap targets

      Larger buttons and links.

      Shopify developer (freelance) 2 hours

    4. 4

      Console errors

      Fix or remove failing scripts.

      Shopify developer (freelance) 2 hours

    5. 5

      Retest

      PageSpeed on phone.

      Shopify developer (freelance) 1 hour

    6. 6

      Watch

      Mobile bounce rate in Shopify analytics.

      Founder and Creative Director monthly

    First result
    1 week
    Cost
    Developer time
    Owner
    Shopify developer (freelance)

    Smallest test

    Fix the Vogue section height and retest.

    Why it works

    Reserve the height of the Vogue section and the banner, serve the banner in a modern format at phone size with high priority, enlarge small tap targets and fix the nine console errors. Retest and keep the score under 0.1.

    A steady, fast page keeps phone shoppers, who arrive mostly from Instagram and press links, browsing instead of bouncing.

    Risks and how to handle them

    • Theme updates undo fixes

      Note the changes for the next theme update.

    Evidence

    • PageSpeed testGoogle PageSpeed test of the homepage on a phone (October 20, 2026): performance 67/100 (desktop 84); the main banner image takes 4.8 s to appear against a 2.5 s target; layout shift 0.246 (the limit for "good" is 0.1), caused by the "Featured in British Vogue" section; 2.2 MB in 276 requests and 5,460 page elements; fixes include image delivery (about 0.35 s, 135 KB) and 289 KB of unused JavaScript; 9 console errors; touch targets too small and low-contrast text.Source
    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
  • 05

    Twenty-three of the 84 products have a blank or "0" product type, and the rest use several spellings for the same thing. Free Google Shopping listings, the shop's own filters and AI shopping assistants all lean on that field to know a sarong from a swimsuit.

    Medium impactLow effort First result in 1 month Studio assistant

    First action

    Fix the 23 products with a blank or "0" type.

    How to measure it

    Free-listing clicks

    Now
    –
    Target
    +100%
    By
    90 days

    Steps

    1. 1

      Pick the list

      Eleven product types.

      Founder and Creative Director 1 hour

    2. 2

      Bulk edit

      Types, colour, material.

      Studio assistant 1 day

    3. 3

      Add categories

      Google product category per type.

      Studio assistant 2 hours

    4. 4

      Check the channel

      Google channel and feed errors.

      Shopify developer (freelance) 2 hours

    5. 5

      Fix rejections

      Images, prices, shipping.

      Studio assistant 1 day

    6. 6

      Measure

      Merchant Center clicks.

      Founder and Creative Director monthly

    First result
    1 month
    Cost
    $0
    Owner
    Studio assistant

    Smallest test

    Bulk-edit the product types this week.

    Why it works

    Set one product type per piece from a short list (Sarong, Swimsuit, Bikini, Tunic, Dress, Silk scarf, Cashmere scarf, Gloves, Book, Journal, Bag), add Google product categories, colour and material, and connect or review the Google channel in Shopify so products show in free listings.

    Clean product data is the cheapest way into Google Shopping, and it makes the site's own browsing work.

    Risks and how to handle them

    • Feed warnings

      Fix one batch a week.

    Evidence

    • Your websiteCatalogue (the store's public product feed, October 20, 2026): 84 products from $13 to $300, median $97.50: sarongs, swimwear, tunics, dresses, scarves, gloves, books and journals. The product type is blank or "0" on 23 products and spelled several ways elsewhere ("Swimwear", "bikini"; "beach tunic", "Beach Tunic", "tunics"; "Scarves", "cashmere scarves", "scarf"). Product pages show no customer reviews.Source
    • DNS checkdanacooper.net uses Google Workspace mail and a Mailchimp newsletter; SPF is "~all" and the DMARC policy is "p=none", so the domain is not protected against spoofed email. The store runs on Shopify and the sitemap has English pages for Bermuda, Canada and the UK.Source
  • 06

    The products have Vogue and Tatler quotes but no customer reviews. Buyers spending $185 on a swimsuit or $275 on cashmere want to hear from other buyers about fit, colour and fabric, and rivals with free returns set high expectations.

    Medium impactLow effort First result in 1 month Founder and Creative Director

    First action

    Send the review request to last year's buyers.

    How to measure it

    Products with at least three reviews

    Now
    –
    Target
    30
    By
    90 days

    Steps

    1. 1

      Pick an app

      One that imports photos.

      Shopify developer (freelance) 1 hour

    2. 2

      Email buyers

      Last 12 months, via Mailchimp.

      Founder and Creative Director 1 day

    3. 3

      Follow up

      One reminder a week later.

      Studio assistant 1 week

    4. 4

      Show stars

      Product and collection pages.

      Shopify developer (freelance) 2 hours

    5. 5

      Reply to reviews

      Fit and care answers.

      Founder and Creative Director weekly

    6. 6

      Automate

      Request 14 days after delivery.

      Shopify developer (freelance) 1 day

    First result
    1 month
    Cost
    Reviews app fee
    Owner
    Founder and Creative Director

    Smallest test

    Email 50 past swimwear buyers.

    Why it works

    Add a reviews app, email past buyers through Mailchimp asking for a review with a photo, and show stars on product and collection pages. Answer fit questions in the replies.

    Reviews with photos and fit notes reduce the doubt that stops first-time buyers, especially with a 7-day return window.

    Risks and how to handle them

    • Few replies

      Offer a small gift (a journal) for photo reviews.

    Evidence

    • Your websiteCatalogue (the store's public product feed, October 20, 2026): 84 products from $13 to $300, median $97.50: sarongs, swimwear, tunics, dresses, scarves, gloves, books and journals. The product type is blank or "0" on 23 products and spelled several ways elsewhere ("Swimwear", "bikini"; "beach tunic", "Beach Tunic", "tunics"; "Scarves", "cashmere scarves", "scarf"). Product pages show no customer reviews.Source
    • Your websiteRefund policy: a 7-day return window after delivery ("RMAs will only be approved if requested within 7 days of an order's arrival"), sale items final, shipping not refunded; a 14-day period for EU orders.Source
    • Competitor researchRivals' own homepages: Lilly Pulitzer sells "resort wear for women" with "Free shipping & returns on all products"; Julia Amory, "classic silhouettes, bold colors, and elevated patterns"; Roller Rabbit, "a feel-good lifestyle brand" with "Free Shipping on Orders +$100"; Vilebrequin, swim shorts with "Tropezian charm with vibrant colours and patterns".Source

This quarter 10

The core plays for the next three months.

  • 07

    The main menu has an "Art Prints" collection with no products, while every collection starts as an original painting and the wedding page says originals are for sale. Visitors who love the artwork but not the sarong have nothing to buy.

    High impactMedium effort First result in 2 months Founder and Creative Director

    First action

    Pick ten illustrations with the most Instagram likes.

    How to measure it

    Monthly print sales

    Now
    –
    Target
    20 prints
    By
    2 quarters

    Steps

    1. 1

      Choose artwork

      Ten pieces.

      Founder and Creative Director 1 week

    2. 2

      Find a printer

      Archival giclée, drop-ship if possible.

      Founder and Creative Director 2 weeks

    3. 3

      Price

      Two sizes, numbered editions.

      Founder and Creative Director 1 day

    4. 4

      Photograph

      Framed in rooms.

      Studio assistant 1 week

    5. 5

      Launch

      Newsletter and Instagram.

      Founder and Creative Director 1 week

    6. 6

      Review

      Best sellers after a quarter.

      Founder and Creative Director quarterly

    First result
    2 months
    Cost
    Print proofs
    Owner
    Founder and Creative Director

    Smallest test

    List three prints as pre-orders.

    Why it works

    Release a first set of signed, numbered prints (Bermuda flora, sailing, the Front Street mosaic study), in two sizes, plus a few originals by enquiry. Photograph them framed in rooms and add them to gift collections.

    Prints have high margins, no sizing returns, and suit visitors and art buyers who do not wear resortwear.

    Risks and how to handle them

    • Printer quality

      Order proofs before listing.

    Evidence

    • Your websiteNeglected corners: the "Bermuda Dispatches" blog's latest post is from November 30, 2023; the "Art Prints" collection in the main menu has 0 products; the YouTube channel has 19 videos, 8 subscribers and 5,984 views in total.Source
    • Your websiteWeddings & Events page: custom invitations, maps, menus, place cards, bridal-party scarves, robes, ties and decor; "Custom wedding illustration packages start at $3,000. Projects are limited to a select number of couples each year"; clients receive print-ready files and "Original paintings are available to purchase". Testimonial from Cece Armstrong: Dana "designed a Bermuda scarf that highlighted venues from the wedding... we gave it as gifts to the wedding party". Enquiries go to a general contact form (name, email, phone, comment).Source
    • Your websiteAbout page: born and raised in Bermuda; BFA from Parsons; art director and designer for W Magazine, Sports Illustrated, The Week, The Washington Post and The Wall Street Journal; Art Director in Beijing; founded the resortwear brand in 2006. Swimwear is SPF 50+ and made in the U.S. with ECONYL regenerated fiber. Children's books (My Bermuda ABC, Pedro 'N' Pip, Octopi Are Very Sly) sell from $13 to $35; clients include Workman Publishing and Chronicle Books.Source
  • 08

    The brand has been sold at The Ritz Jamaica, The Four Seasons, Elisha Daniels at Mandarin Boston, Saks and Palm Beach boutiques, and the retail page invites stores to commission exclusive pieces. There is no wholesale page, line sheet or order minimum for a buyer to act on.

    High impactMedium effort First result in 1 quarter Founder and Creative Director

    First action

    Make the line sheet from the current catalogue.

    How to measure it

    Active wholesale accounts

    Now
    –
    Target
    8
    By
    2 quarters

    Steps

    1. 1

      Write terms

      Minimums, lead times, prices.

      Founder and Creative Director 1 week

    2. 2

      Make the line sheet

      PDF with photos.

      Studio assistant 1 week

    3. 3

      Publish the page

      With an application form.

      Shopify developer (freelance) 2 days

    4. 4

      List boutiques

      Thirty resort shops.

      Studio assistant 1 week

    5. 5

      Email and follow up

      Two touches each.

      Founder and Creative Director 1 month

    6. 6

      Reorder reminders

      Each season.

      Founder and Creative Director quarterly

    First result
    1 quarter
    Cost
    Samples and postage
    Owner
    Founder and Creative Director

    Smallest test

    Email five former stockists the new line sheet.

    Why it works

    Publish a wholesale page with the line sheet (sarongs, swimwear, scarves, books), minimums, lead times and the custom-print option. Email 30 resort boutiques in Bermuda, the Caribbean, Palm Beach and New England with the Vogue feature and the past stockist list.

    Resort boutiques sell to exactly the guests who buy island prints, and each store reorders every season.

    Risks and how to handle them

    • Wholesale margins are thin

      Keep custom-print exclusives at a higher price.

    Evidence

    • Your websitePress and retail pages: the brand "has been carried by numerous stores such as in The Ritz Jamaica, C'Orrcio and The Skinny Dip in Palm Beach, SAKS 5th Avenue, NY, The Four Seasons Hotel, Elisha Daniels at Mandarin Boston"; retailers "can work with Dana to adapt her signature styles or develop custom pieces exclusively for their store"; a private-label resort line for Glamourpuss NYC sold at Saks NYC and Calypso St. Barts.Source
    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
    • Your websiteCatalogue (the store's public product feed, October 20, 2026): 84 products from $13 to $300, median $97.50: sarongs, swimwear, tunics, dresses, scarves, gloves, books and journals. The product type is blank or "0" on 23 products and spelled several ways elsewhere ("Swimwear", "bikini"; "beach tunic", "Beach Tunic", "tunics"; "Scarves", "cashmere scarves", "scarf"). Product pages show no customer reviews.Source
  • 09

    Dana was a licensee for the 35th America's Cup, her father was an Olympic sailor and America's Cup judge, and she offers artwork for "yacht clubs, regattas, marine brands, sailing events". Clubs and regattas buy crew gifts and merchandise every season.

    High impactMedium effort First result in 2 quarters Founder and Creative Director

    First action

    List 20 yacht clubs and regattas to contact.

    How to measure it

    Custom sailing orders

    Now
    –
    Target
    3
    By
    2 quarters

    Steps

    1. 1

      Make the deck

      America's Cup proof, samples, prices.

      Founder and Creative Director 1 week

    2. 2

      Price runs

      Per 50 and 100 pieces.

      Founder and Creative Director 1 week

    3. 3

      List targets

      Clubs and regattas.

      Studio assistant 1 week

    4. 4

      Send and follow up

      Email and a call.

      Founder and Creative Director 1 month

    5. 5

      Produce a sample

      One club scarf design.

      Founder and Creative Director 1 month

    6. 6

      Publish results

      On the sailing page.

      Founder and Creative Director after delivery

    First result
    2 quarters
    Cost
    Samples
    Owner
    Founder and Creative Director

    Smallest test

    Send the deck to five clubs.

    Why it works

    Build a one-page sailing deck (the America's Cup collection, a sample club scarf and tie, prices per 50 and 100 pieces, timeline), and send it to yacht clubs and regatta committees in Bermuda, New England and the Caribbean. Offer a signature print for each event.

    One club order equals dozens of web orders, and the sailing story is credible in a way few designers can match.

    Risks and how to handle them

    • Long lead times

      Pitch nine months before each event.

    Evidence

    • Your websiteSailing & Nautical Design page: Dana "was selected as a licensee for the 35th America's Cup in Bermuda" (2017); her father was "an Olympic sailor and America's Cup judge"; she offers original artwork and merchandise for "yacht clubs, regattas, marine brands, sailing events, and private clients".Source
    • Your websitePress and retail pages: the brand "has been carried by numerous stores such as in The Ritz Jamaica, C'Orrcio and The Skinny Dip in Palm Beach, SAKS 5th Avenue, NY, The Four Seasons Hotel, Elisha Daniels at Mandarin Boston"; retailers "can work with Dana to adapt her signature styles or develop custom pieces exclusively for their store"; a private-label resort line for Glamourpuss NYC sold at Saks NYC and Calypso St. Barts.Source
    • Your websiteWeddings & Events page: custom invitations, maps, menus, place cards, bridal-party scarves, robes, ties and decor; "Custom wedding illustration packages start at $3,000. Projects are limited to a select number of couples each year"; clients receive print-ready files and "Original paintings are available to purchase". Testimonial from Cece Armstrong: Dana "designed a Bermuda scarf that highlighted venues from the wedding... we gave it as gifts to the wedding party". Enquiries go to a general contact form (name, email, phone, comment).Source
  • 10

    The wedding page serves "a destination wedding in Bermuda or a coastal celebration in New England", and a past client praised the venue scarf given to the wedding party. Planners and venues meet these couples months before they choose a designer.

    High impactMedium effort First result in 2 quarters Founder and Creative Director

    First action

    List 25 planners and venues.

    How to measure it

    Referred wedding bookings

    Now
    –
    Target
    4 a year
    By
    3 quarters

    Steps

    1. 1

      Make the kit

      PDF and sample scarf.

      Founder and Creative Director 2 weeks

    2. 2

      List planners

      Bermuda and New England.

      Studio assistant 1 week

    3. 3

      Send kits

      With a personal note.

      Founder and Creative Director 2 weeks

    4. 4

      Follow up

      A call or coffee.

      Founder and Creative Director 1 month

    5. 5

      Set the referral terms

      Fee or discount.

      Founder and Creative Director 1 week

    6. 6

      Track

      Enquiry source on the wedding form.

      Studio assistant monthly

    First result
    2 quarters
    Cost
    Samples and postage
    Owner
    Founder and Creative Director

    Smallest test

    Send three planner kits.

    Why it works

    Send a planner kit (portfolio PDF, a sample scarf, process and prices from $3,000) to 25 Bermuda and New England planners and venues, offer a referral fee or planner discount, and ask for a listing on their vendor pages.

    Couples trust their planner's list; one planner can send several couples a year.

    Risks and how to handle them

    • Planners have favourite designers

      Lead with the custom scarf, which most do not offer.

    Evidence

    • Your websiteWeddings & Events page: custom invitations, maps, menus, place cards, bridal-party scarves, robes, ties and decor; "Custom wedding illustration packages start at $3,000. Projects are limited to a select number of couples each year"; clients receive print-ready files and "Original paintings are available to purchase". Testimonial from Cece Armstrong: Dana "designed a Bermuda scarf that highlighted venues from the wedding... we gave it as gifts to the wedding party". Enquiries go to a general contact form (name, email, phone, comment).Source
    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
  • 11

    A past client's favourite piece was "a Bermuda scarf that highlighted venues from the wedding", given to the wedding party. Today that scarf lives inside packages from $3,000, so couples with smaller budgets, or who already have stationery, have no way to buy it.

    High impactMedium effort First result in 1 quarter Founder and Creative Director

    First action

    Price a 10- and 25-scarf run with the printer.

    How to measure it

    Scarf packages

    Now
    –
    Target
    10 a year
    By
    3 quarters

    Steps

    1. 1

      Price runs

      10, 25, 50 scarves.

      Founder and Creative Director 1 week

    2. 2

      Set the process

      Brief, sketch, two revisions.

      Founder and Creative Director 1 week

    3. 3

      Make the page

      With the Armstrong story.

      Shopify developer (freelance) 1 week

    4. 4

      Add to the wedding form

      As a pieces option.

      Shopify developer (freelance) 1 day

    5. 5

      Tell planners

      In the planner kit.

      Founder and Creative Director ongoing

    6. 6

      Review

      Upsells to full packages.

      Founder and Creative Director quarterly

    First result
    1 quarter
    Cost
    Sample run
    Owner
    Founder and Creative Director

    Smallest test

    Offer the package to the next three wedding enquiries.

    Why it works

    Offer a fixed "wedding party scarf" package: one custom design with your venues and colours, a minimum of 10 scarves, a set timeline and price per scarf. Add the same for anniversaries and family reunions.

    A clear entry product widens the market for custom work and often leads to stationery and decor later.

    Risks and how to handle them

    • Margins on small runs

      Set a 10-scarf minimum.

    Evidence

    • Your websiteWeddings & Events page: custom invitations, maps, menus, place cards, bridal-party scarves, robes, ties and decor; "Custom wedding illustration packages start at $3,000. Projects are limited to a select number of couples each year"; clients receive print-ready files and "Original paintings are available to purchase". Testimonial from Cece Armstrong: Dana "designed a Bermuda scarf that highlighted venues from the wedding... we gave it as gifts to the wedding party". Enquiries go to a general contact form (name, email, phone, comment).Source
    • Your websiteGift collections already in the shop: "Valentines Day Gifting" (cashmere and silk scarves, a $45 clutch), "Pre-order now for the holidays: the Bermuda scarf" (two $225 silk scarves), Bermuda journals at $18 and children's books.Source
  • 12

    The blog's last post is from November 2023, though the site has a Bermuda Travel Tips page and an audience of visitors. People planning a Bermuda trip or wedding search for what to pack, where to shop and what to bring home.

    Medium impactLow effort First result in 2 quarters Founder and Creative Director

    First action

    Write "What to pack for Bermuda in winter".

    How to measure it

    Blog visits from search

    Now
    –
    Target
    1,000 a month
    By
    3 quarters

    Steps

    1. 1

      Plan topics

      Twelve months.

      Founder and Creative Director 1 day

    2. 2

      Write

      One post a month.

      Founder and Creative Director monthly

    3. 3

      Link products

      Two or three per post.

      Studio assistant monthly

    4. 4

      Send

      Newsletter.

      Founder and Creative Director monthly

    5. 5

      Pin

      Each post to Pinterest.

      Studio assistant monthly

    6. 6

      Measure

      Search traffic and sales.

      Founder and Creative Director quarterly

    First result
    2 quarters
    Cost
    Writing time
    Owner
    Founder and Creative Director

    Smallest test

    Publish one packing guide this month.

    Why it works

    Publish one post a month: what to pack for Bermuda by season, Bermuda shorts etiquette, a wedding guest guide, local makers and markets, with the right pieces linked in each. Send each post to the newsletter.

    Useful travel content earns search traffic from exactly the people about to buy resortwear and Bermuda gifts.

    Risks and how to handle them

    • Time

      Short, useful posts beat long ones.

    Evidence

    • Your websiteNeglected corners: the "Bermuda Dispatches" blog's latest post is from November 30, 2023; the "Art Prints" collection in the main menu has 0 products; the YouTube channel has 19 videos, 8 subscribers and 5,984 views in total.Source
    • Your websiteAbout page: born and raised in Bermuda; BFA from Parsons; art director and designer for W Magazine, Sports Illustrated, The Week, The Washington Post and The Wall Street Journal; Art Director in Beijing; founded the resortwear brand in 2006. Swimwear is SPF 50+ and made in the U.S. with ECONYL regenerated fiber. Children's books (My Bermuda ABC, Pedro 'N' Pip, Octopi Are Very Sly) sell from $13 to $35; clients include Workman Publishing and Chronicle Books.Source
    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
  • 13

    The shop already offers "Bermuda orders arrange local pick up & drop off". Visitors staying a week in Bermuda want a local, designer-made souvenir but rarely find a studio. Hotel concierges and guest-house hosts are asked where to shop every day.

    Medium impactLow effort First result in 1 quarter Founder and Creative Director

    First action

    Design the QR card and ask three hotels.

    How to measure it

    Visitor orders

    Now
    –
    Target
    15 a month
    By
    2 quarters

    Steps

    1. 1

      Write the page

      Order, drop-off, timing.

      Founder and Creative Director 1 day

    2. 2

      Set the code

      Guest discount by hotel.

      Shopify developer (freelance) 1 day

    3. 3

      Print cards

      QR to the page.

      Studio assistant 1 week

    4. 4

      Visit concierges

      Ten hotels and guest houses.

      Founder and Creative Director 1 month

    5. 5

      Deliver

      Within two days.

      Studio assistant ongoing

    6. 6

      Track

      Orders by hotel code.

      Founder and Creative Director monthly

    First result
    1 quarter
    Cost
    Printing
    Owner
    Founder and Creative Director

    Smallest test

    Leave cards at three hotels for a month.

    Why it works

    Make a "Visiting Bermuda?" page: order online, choose hotel drop-off, delivered within two days. Give hotel and guest-house concierges a small card with a QR code and a guest discount, and track orders by code.

    It turns the local pick-up option into a channel for the island's visitors, with no shop rent.

    Risks and how to handle them

    • Delivery time

      Hold a small stock for best sellers.

    Evidence

    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
    • Your websiteGift collections already in the shop: "Valentines Day Gifting" (cashmere and silk scarves, a $45 clutch), "Pre-order now for the holidays: the Bermuda scarf" (two $225 silk scarves), Bermuda journals at $18 and children's books.Source
    • Your websiteAbout page: born and raised in Bermuda; BFA from Parsons; art director and designer for W Magazine, Sports Illustrated, The Week, The Washington Post and The Wall Street Journal; Art Director in Beijing; founded the resortwear brand in 2006. Swimwear is SPF 50+ and made in the U.S. with ECONYL regenerated fiber. Children's books (My Bermuda ABC, Pedro 'N' Pip, Octopi Are Very Sly) sell from $13 to $35; clients include Workman Publishing and Chronicle Books.Source
  • 14

    The shop has $18 journals, $13–$35 children's books, $45 clutches and $100–$275 scarves, plus gift collections for Valentine's Day and holiday scarves, but no ready-made gift set. Visitors and family abroad want one Bermuda present that arrives wrapped.

    Medium impactLow effort First result in 1 month Founder and Creative Director

    First action

    Price the three sets.

    How to measure it

    Average order value

    Now
    –
    Target
    +20%
    By
    2 quarters

    Steps

    1. 1

      Design sets

      Three price points.

      Founder and Creative Director 1 week

    2. 2

      Packaging

      Wrap and card.

      Studio assistant 1 week

    3. 3

      List

      As bundles in Shopify.

      Shopify developer (freelance) 1 day

    4. 4

      Photograph

      Wrapped and open.

      Studio assistant 1 day

    5. 5

      Promote

      Homepage and newsletter.

      Founder and Creative Director 1 week

    6. 6

      Review

      Best set by season.

      Founder and Creative Director quarterly

    First result
    1 month
    Cost
    Packaging
    Owner
    Founder and Creative Director

    Smallest test

    List one gift set this week.

    Why it works

    Create three sets (a Baby Bermuda set with the ABC book and a sarong, a Traveller set with a journal and chiffon scarf, a Luxury set with cashmere and a print), gift-wrapped with a card, and feature them on the homepage year-round.

    Sets raise the order value and make choosing easy for gift buyers who do not know sizes.

    Risks and how to handle them

    • Stock tied up in sets

      Build sets to order.

    Evidence

    • Your websiteGift collections already in the shop: "Valentines Day Gifting" (cashmere and silk scarves, a $45 clutch), "Pre-order now for the holidays: the Bermuda scarf" (two $225 silk scarves), Bermuda journals at $18 and children's books.Source
    • Your websiteAbout page: born and raised in Bermuda; BFA from Parsons; art director and designer for W Magazine, Sports Illustrated, The Week, The Washington Post and The Wall Street Journal; Art Director in Beijing; founded the resortwear brand in 2006. Swimwear is SPF 50+ and made in the U.S. with ECONYL regenerated fiber. Children's books (My Bermuda ABC, Pedro 'N' Pip, Octopi Are Very Sly) sell from $13 to $35; clients include Workman Publishing and Chronicle Books.Source
    • Your websiteCatalogue (the store's public product feed, October 20, 2026): 84 products from $13 to $300, median $97.50: sarongs, swimwear, tunics, dresses, scarves, gloves, books and journals. The product type is blank or "0" on 23 products and spelled several ways elsewhere ("Swimwear", "bikini"; "beach tunic", "Beach Tunic", "tunics"; "Scarves", "cashmere scarves", "scarf"). Product pages show no customer reviews.Source
  • 15

    The shop has a Mailchimp newsletter, but its domain's DMARC policy is "p=none", so emails can be spoofed and inbox placement suffers. Buyers come from three very different worlds: Bermuda locals, US resort shoppers and wedding clients.

    Medium impactLow effort First result in 1 month Founder and Creative Director

    First action

    Add DMARC reporting and write the first welcome email.

    How to measure it

    Email-attributed revenue

    Now
    –
    Target
    15% of sales
    By
    2 quarters

    Steps

    1. 1

      Check senders

      Workspace, Mailchimp, Shopify.

      Shopify developer (freelance) 1 day

    2. 2

      Enforce DMARC

      Quarantine after two clean weeks.

      Shopify developer (freelance) 2 weeks

    3. 3

      Write the welcome series

      Three emails.

      Founder and Creative Director 1 week

    4. 4

      Write the post-purchase series

      Care, review, matching pieces.

      Founder and Creative Director 1 week

    5. 5

      Segment

      Bermuda, US, weddings.

      Studio assistant 1 day

    6. 6

      Measure

      Opens, clicks, sales.

      Founder and Creative Director monthly

    First result
    1 month
    Cost
    $0
    Owner
    Founder and Creative Director

    Smallest test

    Write and switch on the first welcome email.

    Why it works

    Move DMARC to "quarantine" after checking senders, then set up a welcome series (Dana's story, the Vogue features, best sellers), a post-purchase series (care tips, review request, matching pieces) and a segment for Bermuda locals with pick-up news.

    Automated emails sell while Dana paints, and better authentication gets them into the inbox.

    Risks and how to handle them

    • Blocking a real sender

      Read DMARC reports before enforcing.

    Evidence

    • DNS checkdanacooper.net uses Google Workspace mail and a Mailchimp newsletter; SPF is "~all" and the DMARC policy is "p=none", so the domain is not protected against spoofed email. The store runs on Shopify and the sitemap has English pages for Bermuda, Canada and the UK.Source
    • Your websiteAbout page: born and raised in Bermuda; BFA from Parsons; art director and designer for W Magazine, Sports Illustrated, The Week, The Washington Post and The Wall Street Journal; Art Director in Beijing; founded the resortwear brand in 2006. Swimwear is SPF 50+ and made in the U.S. with ECONYL regenerated fiber. Children's books (My Bermuda ABC, Pedro 'N' Pip, Octopi Are Very Sly) sell from $13 to $35; clients include Workman Publishing and Chronicle Books.Source
    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
  • 16

    The site footer links to Pinterest and Google already sees a verified Pinterest account, but wedding stationery, destination wedding ideas and resort outfits are planned on Pinterest boards months ahead. Dana's colourful, illustrated work is made for it.

    Medium impactLow effort First result in 2 months Studio assistant

    First action

    Connect the catalogue to Pinterest.

    How to measure it

    Pinterest visits

    Now
    –
    Target
    500 a month
    By
    2 quarters

    Steps

    1. 1

      Connect the catalogue

      Product pins.

      Shopify developer (freelance) 2 hours

    2. 2

      Make boards

      Weddings, resortwear, nautical.

      Studio assistant 1 day

    3. 3

      Pin wedding work

      Each suite with a description.

      Studio assistant 1 week

    4. 4

      Pin weekly

      Five new pins.

      Studio assistant weekly

    5. 5

      Link posts

      Blog posts as pins.

      Studio assistant monthly

    6. 6

      Review

      Top pins and sales.

      Founder and Creative Director monthly

    First result
    2 months
    Cost
    $0
    Owner
    Studio assistant

    Smallest test

    Pin ten wedding pieces this week.

    Why it works

    Turn on product pins from the Shopify catalogue, make boards for Bermuda weddings, island resortwear and nautical style, and pin each wedding suite, print and blog post with keyword-rich descriptions. Check which pins bring visits monthly.

    Pins keep sending visitors for months, unlike posts that fade in a day.

    Risks and how to handle them

    • Slow start

      Pinterest takes months; keep a steady rhythm.

    Evidence

    • Your websiteWeddings & Events page: custom invitations, maps, menus, place cards, bridal-party scarves, robes, ties and decor; "Custom wedding illustration packages start at $3,000. Projects are limited to a select number of couples each year"; clients receive print-ready files and "Original paintings are available to purchase". Testimonial from Cece Armstrong: Dana "designed a Bermuda scarf that highlighted venues from the wedding... we gave it as gifts to the wedding party". Enquiries go to a general contact form (name, email, phone, comment).Source
    • Your websiteNeglected corners: the "Bermuda Dispatches" blog's latest post is from November 30, 2023; the "Art Prints" collection in the main menu has 0 products; the YouTube channel has 19 videos, 8 subscribers and 5,984 views in total.Source
    • Your websiteCatalogue (the store's public product feed, October 20, 2026): 84 products from $13 to $300, median $97.50: sarongs, swimwear, tunics, dresses, scarves, gloves, books and journals. The product type is blank or "0" on 23 products and spelled several ways elsewhere ("Swimwear", "bikini"; "beach tunic", "Beach Tunic", "tunics"; "Scarves", "cashmere scarves", "scarf"). Product pages show no customer reviews.Source

Big bets 3

Larger plays that can change the trajectory.

  • 17

    Dana has two decades of original island prints and has already designed for Workman, Chronicle Books, Saks, Glamourpuss NYC and the America's Cup; the wedding page shows the artwork on tablecloths, napkins and backdrops. Licensing lets other companies make and sell the products while she earns a royalty.

    High impactHigh effort First result in 3 quarters Founder and Creative Director

    First action

    Pick 20 prints and put them in repeat.

    How to measure it

    Signed licences

    Now
    –
    Target
    2
    By
    4 quarters

    Steps

    1. 1

      Build the portfolio

      20 prints, past work, terms.

      Founder and Creative Director 1 month

    2. 2

      Find a lawyer

      Standard licence agreement.

      Founder and Creative Director 2 weeks

    3. 3

      List brands

      Five categories.

      Studio assistant 2 weeks

    4. 4

      Pitch

      Email and a trade show visit.

      Founder and Creative Director 1 quarter

    5. 5

      Sign one

      Royalties on sales.

      Founder and Creative Director 1 quarter

    6. 6

      Promote

      Announce the collaboration.

      Founder and Creative Director on launch

    First result
    3 quarters
    Cost
    Legal fees and travel
    Owner
    Founder and Creative Director

    Smallest test

    Send the portfolio to three table-linen brands.

    Why it works

    Build a licensing portfolio (20 signature prints in repeat, past licences, terms), and approach five categories: table linen, hotel amenities, stationery, beach towels and puzzles. Start with one licence and royalties paid on sales.

    Licensing scales the artwork without Dana carrying stock or production, and the America's Cup licence shows she can deliver.

    Risks and how to handle them

    • Poor quality products

      Approve samples before launch.

    Evidence

    • Your websitePress and retail pages: the brand "has been carried by numerous stores such as in The Ritz Jamaica, C'Orrcio and The Skinny Dip in Palm Beach, SAKS 5th Avenue, NY, The Four Seasons Hotel, Elisha Daniels at Mandarin Boston"; retailers "can work with Dana to adapt her signature styles or develop custom pieces exclusively for their store"; a private-label resort line for Glamourpuss NYC sold at Saks NYC and Calypso St. Barts.Source
    • Your websiteSailing & Nautical Design page: Dana "was selected as a licensee for the 35th America's Cup in Bermuda" (2017); her father was "an Olympic sailor and America's Cup judge"; she offers original artwork and merchandise for "yacht clubs, regattas, marine brands, sailing events, and private clients".Source
    • Your websiteAbout page: born and raised in Bermuda; BFA from Parsons; art director and designer for W Magazine, Sports Illustrated, The Week, The Washington Post and The Wall Street Journal; Art Director in Beijing; founded the resortwear brand in 2006. Swimwear is SPF 50+ and made in the U.S. with ECONYL regenerated fiber. Children's books (My Bermuda ABC, Pedro 'N' Pip, Octopi Are Very Sly) sell from $13 to $35; clients include Workman Publishing and Chronicle Books.Source
    • Your websiteWeddings & Events page: custom invitations, maps, menus, place cards, bridal-party scarves, robes, ties and decor; "Custom wedding illustration packages start at $3,000. Projects are limited to a select number of couples each year"; clients receive print-ready files and "Original paintings are available to purchase". Testimonial from Cece Armstrong: Dana "designed a Bermuda scarf that highlighted venues from the wedding... we gave it as gifts to the wedding party". Enquiries go to a general contact form (name, email, phone, comment).Source
  • 18

    Dana has been recommended by British Vogue several times since 2023 and featured again in May–July 2026, and the shop already has UK pages and duty-paid shipping. Yet the announcement bar says US-only, and there is no UK-specific offer.

    High impactMedium effort First result in 2 quarters Founder and Creative Director

    First action

    Check the UK checkout and prices in pounds.

    How to measure it

    UK orders

    Now
    –
    Target
    30 a quarter
    By
    3 quarters

    Steps

    1. 1

      Fix shipping

      See the shipping clean-up idea.

      Founder and Creative Director 1 week

    2. 2

      Set GBP prices

      Rounded local prices.

      Shopify developer (freelance) 1 day

    3. 3

      Make ads

      Vogue feature and best sellers.

      Founder and Creative Director 1 week

    4. 4

      Run the test

      Small budget, one month.

      Founder and Creative Director 1 month

    5. 5

      Pitch press

      Two editors, one boutique.

      Founder and Creative Director 1 month

    6. 6

      Decide

      Scale or stop.

      Founder and Creative Director 1 quarter

    First result
    2 quarters
    Cost
    Test ad budget
    Owner
    Founder and Creative Director

    Smallest test

    Run one UK ad for two weeks.

    Why it works

    Once shipping is fixed, run a small Instagram and Pinterest test in the UK using the Vogue feature, with GBP prices and a UK delivery promise. Pitch two UK resort and travel editors and one London boutique.

    A market that has already seen the brand in its leading fashion magazine is the cheapest one to open.

    Risks and how to handle them

    • Returns from abroad

      Clear sizing notes and the EU/UK return terms.

    Builds on

    Evidence

    • Your websiteHomepage: titled "Fashion Illustrator & Designer for Luxury Brands"; "Featured in British Vogue (May–July 2026)"; three studio specialties (Weddings & Events Design, Retail & Custom Design, Editorial & Art Direction); work that "has appeared in VOGUE, The Wall Street Journal, and Saks Fifth Avenue"; an America's Cup licensing testimonial and "As Seen In TATLER Magazine, May 2024". The announcement bar reads "Shipping available for US-based orders | Bermuda orders arrange local pick up & drop off".Source
    • DNS checkdanacooper.net uses Google Workspace mail and a Mailchimp newsletter; SPF is "~all" and the DMARC policy is "p=none", so the domain is not protected against spoofed email. The store runs on Shopify and the sitemap has English pages for Bermuda, Canada and the UK.Source
    • Your websiteShipping policy: "International shipping is currently available to most countries", sent Delivered Duty Paid with Passport and "typically delivered within 8 -14 business days" (Canada excluded from duty-paid shipping); it tells customers to track orders on "your India/Julia Amory tracking page".Source
  • 19

    The wedding page already offers organizations "custom designed pieces... for the special event", and Dana has designed for the America's Cup and a Front Street department store. Bermuda is home to many international insurance and finance firms that host clients and conferences and need gifts with a sense of place.

    High impactMedium effort First result in 2 quarters Founder and Creative Director

    First action

    Make a one-page corporate gifting sheet.

    How to measure it

    Corporate gift orders

    Now
    –
    Target
    4 a year
    By
    3 quarters

    Steps

    1. 1

      Design the offer

      Products, prices, timeline.

      Founder and Creative Director 2 weeks

    2. 2

      Make samples

      A scarf and tie with a sample logo print.

      Founder and Creative Director 1 month

    3. 3

      List companies

      Ten firms and conference hotels.

      Studio assistant 1 week

    4. 4

      Pitch

      Email and meeting.

      Founder and Creative Director 1 quarter

    5. 5

      Deliver one

      Case study with photos.

      Founder and Creative Director 1 quarter

    6. 6

      Repeat

      Annual reminder.

      Founder and Creative Director yearly

    First result
    2 quarters
    Cost
    Samples
    Owner
    Founder and Creative Director

    Smallest test

    Pitch three event managers.

    Why it works

    Create a corporate gifting offer: a custom print for a company or conference, applied to scarves, ties, pocket squares and journals, at set prices per 50 and 100 pieces. Approach event managers at ten firms and the island's conference hotels.

    Corporate orders are large, repeat every year and need exactly what Dana offers: a Bermuda design no one else has.

    Risks and how to handle them

    • Company brand rules

      Keep logos subtle and approved in writing.

    Evidence

    • Your websiteWeddings & Events page: custom invitations, maps, menus, place cards, bridal-party scarves, robes, ties and decor; "Custom wedding illustration packages start at $3,000. Projects are limited to a select number of couples each year"; clients receive print-ready files and "Original paintings are available to purchase". Testimonial from Cece Armstrong: Dana "designed a Bermuda scarf that highlighted venues from the wedding... we gave it as gifts to the wedding party". Enquiries go to a general contact form (name, email, phone, comment).Source
    • Your websiteSailing & Nautical Design page: Dana "was selected as a licensee for the 35th America's Cup in Bermuda" (2017); her father was "an Olympic sailor and America's Cup judge"; she offers original artwork and merchandise for "yacht clubs, regattas, marine brands, sailing events, and private clients".Source
    • Your websitePress and retail pages: the brand "has been carried by numerous stores such as in The Ritz Jamaica, C'Orrcio and The Skinny Dip in Palm Beach, SAKS 5th Avenue, NY, The Four Seasons Hotel, Elisha Daniels at Mandarin Boston"; retailers "can work with Dana to adapt her signature styles or develop custom pieces exclusively for their store"; a private-label resort line for Glamourpuss NYC sold at Saks NYC and Calypso St. Barts.Source

Wildcards 2

Unexpected experiments, each with a cheap way to test it.

  • 20

    Dana designed adaptive Bermuda shorts with tear-away sides and brass fasteners after a friend in a hip cast could not get shorts on, and the shop lists seven styles. The story ran in The Royal Gazette in 2021 but is barely visible on the site.

    Medium impactLow effort First result in 1 quarter Founder and Creative Director

    First action

    Write the adaptive shorts page.

    How to measure it

    Adaptive shorts orders

    Now
    –
    Target
    +100%
    By
    2 quarters

    Steps

    1. 1

      Write the page

      Story and how it works.

      Founder and Creative Director 1 week

    2. 2

      Photograph

      On a model with a cast or chair.

      Studio assistant 2 weeks

    3. 3

      Contact press

      Adaptive fashion writers.

      Founder and Creative Director 1 month

    4. 4

      Contact clinics

      Orthopedic and physio.

      Studio assistant 1 month

    5. 5

      Add reviews

      From wearers.

      Founder and Creative Director ongoing

    6. 6

      Review

      Sales and enquiries.

      Founder and Creative Director quarterly

    First result
    1 quarter
    Cost
    Photography
    Owner
    Founder and Creative Director

    Smallest test

    Publish the page and send it to two writers.

    Why it works

    Give the adaptive shorts their own page with the story, how they work and who they help (casts, wheelchair users, post-surgery). Contact adaptive fashion writers, physiotherapy and orthopedic clinics, and disability sports groups.

    Few designers serve adaptive menswear with style; it is a story press likes and a real need with little competition.

    Risks and how to handle them

    • Sensitive marketing

      Work with wearers and use their words.

    Evidence

    • News coverageThe Royal Gazette (December 2021): Dana designed adaptive Bermuda shorts after an athlete friend in a hip-length cast could not get shorts on; the shop's "mens-adaptive-shorts" collection lists seven styles at $115–$125 with "discreet tear-away functionality with brass side fasteners". She also showed at Alliance Française's "Bermuda Meets France" runway (May 2025) and a pop-up at Habitat for Humanity Bermuda's ReStore.Source
    • Your websiteCatalogue (the store's public product feed, October 20, 2026): 84 products from $13 to $300, median $97.50: sarongs, swimwear, tunics, dresses, scarves, gloves, books and journals. The product type is blank or "0" on 23 products and spelled several ways elsewhere ("Swimwear", "bikini"; "beach tunic", "Beach Tunic", "tunics"; "Scarves", "cashmere scarves", "scarf"). Product pages show no customer reviews.Source
  • 21

    The YouTube channel has 19 videos, 8 subscribers and fewer than 6,000 views in total, yet every product "begins with a sketch". Watching an artist paint is some of the most shared short-form content, and it explains the prices.

    Medium impactLow effort First result in 1 quarter Founder and Creative Director

    First action

    Film the next design from the first sketch.

    How to measure it

    Short-video views

    Now
    –
    Target
    50,000 a quarter
    By
    2 quarters

    Steps

    1. 1

      Set up a phone stand

      Above the desk.

      Studio assistant 1 day

    2. 2

      Film

      Each new design.

      Founder and Creative Director weekly

    3. 3

      Edit

      Short cuts with music.

      Studio assistant weekly

    4. 4

      Post

      Reels, TikTok, Shorts.

      Studio assistant weekly

    5. 5

      Add to pages

      Product page video.

      Shopify developer (freelance) monthly

    6. 6

      Review

      Top videos and clicks.

      Founder and Creative Director monthly

    First result
    1 quarter
    Cost
    Phone stand
    Owner
    Founder and Creative Director

    Smallest test

    Post one sketch-to-sarong video this week.

    Why it works

    Film each new design from first sketch to painted artwork to finished product in 30–60 seconds, and post it to Instagram Reels, TikTok and YouTube Shorts with a link to the piece. Use the same clips on product pages.

    Process videos build attachment to the artwork and justify the price of a $275 scarf.

    Risks and how to handle them

    • Time away from painting

      Film while working; edit in batches.

    Evidence

    • Your websiteNeglected corners: the "Bermuda Dispatches" blog's latest post is from November 30, 2023; the "Art Prints" collection in the main menu has 0 products; the YouTube channel has 19 videos, 8 subscribers and 5,984 views in total.Source
    • Your websiteAbout page: born and raised in Bermuda; BFA from Parsons; art director and designer for W Magazine, Sports Illustrated, The Week, The Washington Post and The Wall Street Journal; Art Director in Beijing; founded the resortwear brand in 2006. Swimwear is SPF 50+ and made in the U.S. with ECONYL regenerated fiber. Children's books (My Bermuda ABC, Pedro 'N' Pip, Octopi Are Very Sly) sell from $13 to $35; clients include Workman Publishing and Chronicle Books.Source

03

How Programmable can help

Where an idea in this playbook is something Programmable builds or runs, it's listed here with what we'd do. Everything else is yours to run.

ProgrammableDigital

Show it, don't just describe it

These ideas need something to show: a demo, a video, an animation, graphics or a deck. Digital turns screenshots or the site into all of them, in the company's own brand.

Make a demo (opens programmable.digital in a new tab)
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See every playbook and website review

Independent research. Programmable wrote this playbook from public sources, as they stood on October 21, 2026, and cites them throughout. Dana Cooper Designs did not commission, review or endorse it, and Programmable is not affiliated with Dana Cooper Designs. Company and product names are trademarks of their owners, used only to identify them. The ideas are suggestions and opinion, not professional, legal or financial advice, and not statements about how Dana Cooper Designs runs its business.

Something wrong, or do you represent Dana Cooper Designs? Email [email protected] and we will correct it or take it down.

30/60/90 roadmap

What to focus on in each month, and the ideas that carry it.

  1. Days 1 to 307 ideas

    Shipping message and policy, cashmere waitlist, wedding enquiry form, phone layout fix, product data and reviews; welcome emails and DMARC.

  2. Days 31 to 6011 ideas

    Art prints, wholesale, regatta pitches, planners, the wedding party scarf, Bermuda Dispatches, visitor drop-off, gift sets and Pinterest; adaptive shorts and process videos.

  3. Days 61 to 903 ideas

    Commit to the big bets: licensing, the UK test and corporate gifting.

The research behind the plan

2 research areas, each summarised in a few lines. Open any of them for the full detail.

Customers

What customers say

Customers value original, colourful island prints. The most cited problem: unclear whether the shop ships abroad.

  • Personal, one-of-a-kind wedding design
  • Sold-out favourites
  • In their words: “island style”

Market

Competitive landscape

4 competitors compared: Lilly Pulitzer, Julia Amory, Roller Rabbit and Vilebrequin.

  • Gap to exploit: Custom prints for weddings, clubs and companies
  • Lilly Pulitzer: Mass-produced; no custom work
  • Julia Amory: No island artist story

From the team that wrote this playbook

All products
  • ProgrammableAgencyWorking AI systems in days, not quarters (opens programmable.agency in a new tab)
  • ProgrammableInfoAn agent that finds, researches and asks first (opens programmable.info in a new tab)
  • ProgrammableDigitalScreenshots in, an animated product demo out (opens programmable.digital in a new tab)
  • ProgrammableWatchKnow the day a supplier falls out of compliance (opens programmable.watch in a new tab)
  • ProgrammableTalkGet registrants for your events, and know who’s coming (opens programmable.talk in a new tab)
  • ProgrammablePageText what you need, your customer gets a page that works (opens programmable.page in a new tab)
  • ProgrammableCommunityForums with labelled AI members, never empty (opens programmable.community in a new tab)
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