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Generated Oct 22, 2026
  1. Programmable
  2. Playbooks
  3. Squarespace
Squarespace logo

growth playbook · Oct 22, 2026

squarespace.com (opens in a new tab)

Squarespace growth playbook

Diagnosis

Squarespace has served 14M+ entrepreneurs and is now a private company under Permira, and its hiring points to three priorities: international growth in Germany and France with an AI-discovery playbook, a rebuilt growth and GTM system for a growing product portfolio (Forma, AI credits, mobile, Acuity payments), and a domains business run as its own P&L.

The quickest wins are on its own site: the German and French pricing pages tell search engines and AI assistants the plans are US-only and in dollars, most translated pages declare no language alternates, the homepage fails Core Web Vitals for real visitors, and thousands of old sponsor pages fill the sitemap.

This playbook fixes those first, then adds attach, activation and measurement programs and two bigger bets on AI-assistant domain sales and a data index.

Growth Score

7/10

Biggest Opportunity

Make the translated sites findable and correct in search and AI answers, then turn domains, free tools and trials into more paying sites.

Biggest Risk

AI-first builders (Framer, Lovable, Wix with AI) and cheap hosts (Hostinger, IONOS) compete for new business owners, and an AI pricing model that confuses buyers or squeezes margin could slow the Forma launch.

01

Start here

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

  1. 1

    Tell search engines and AI assistants that the German and French pricing pages are for Europe, not the US only

    Open de.squarespace.com/preise, view source and search for "eligibleRegion"; agree the correct currency and region per market.

    High impact First result in 1 month
  2. 2

    Make the Jimdo, IONOS and e-monsite comparisons the centrepiece of German and French AI discovery

    Pull current search impressions for the three pages by country.

    High impact First result in 1 quarter
  3. 3

    Get the homepage to pass Core Web Vitals: a website builder's own front door is its demo

    Run the PageSpeed report and list the five heaviest requests on the homepage.

    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.

  • 8 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 · 1Big bets · 12Fill-ins · 5Reconsider · 3
Effort →

Showing 21 of 21 ideas

This week 6

Quick wins with a clear first action.

  • 01

    Squarespace is hiring a Dublin lead for Germany and France whose job includes AEO, and a New York manager to build the "AI-discovery strategy" for international markets. Yet the structured data on de.squarespace.com/preise describes all eight plans as US-dollar offers available only in the US ("eligibleRegion": "US", Basic — Jährlich 228.00 USD), and the French /tarification page says the same. On top of that, 76 of 80 sampled pages, including /pricing, /templates, every comparison page and the German and French pricing pages, declare no language alternates, so nothing tells Google which version to show a searcher in Munich or Lyon.

    High impactLow effort First result in 1 month International Strategy and Ma…

    First action

    Open de.squarespace.com/preise, view source and search for "eligibleRegion"; agree the correct currency and region per market.

    How to measure it

    Trial starts from de. and fr. organic search

    Now
    –
    Target
    +15%
    By
    90 days

    Steps

    1. 1

      Confirm billing reality

      Which currency each market is billed in today.

      Senior Lead, AI Pricing & Margin Strategy 2 days

    2. 2

      Fix the offer markup

      Locale-aware priceCurrency, price and eligibleRegion on every pricing page.

      Web Engineering Lead 1 week

    3. 3

      Add hreflang clusters

      Pricing, templates, compare, solutions and blog page types.

      SEO Lead 2 weeks

    4. 4

      Validate

      Rich Results Test and Search Console international targeting report.

      SEO Lead 2 days

    5. 5

      Baseline answers

      Ask Google and the main AI assistants pricing questions in German and French.

      International Strategy and Marketing Lead 1 day

    6. 6

      Re-test and report

      Same questions four and eight weeks later; trial starts by locale.

      Senior Manager International Strategy 8 weeks

    First result
    1 month
    Cost
    Engineering time only
    Owner
    International Strategy and Marketing Lead

    Smallest test

    Fix the German pricing page markup alone and compare its search appearance after two weeks.

    Why it works

    Generate the pricing page offers per locale: the currency the market is actually billed in, the matching price and an eligible region for that market (or drop eligibleRegion if plans are sold everywhere). Then add hreflang clusters to every translated page type, starting with pricing, templates, the 24 comparison pages and the top blog posts, and add self-referencing canonicals to the localized slugs (/preise, /tarification). Re-test how assistants and Google answer "Squarespace Preise" and "Squarespace tarifs" before and after.

    Pricing questions are the most common pre-purchase query to search and AI assistants, and they answer from structured data. Fixing a template-level field corrects every market at once, and hreflang stops the English and local pages competing with each other.

    Ready to use

    ChecklistInternational pricing page check

    [ ] priceCurrency matches the market on /preise, /tarification and the other locales
    [ ] eligibleRegion lists the market (or is removed)
    [ ] hreflang cluster on pricing, templates, compare and blog pages
    [ ] Self-canonical on each localized slug
    [ ] x-default points to the English page
    [ ] Rich Results Test passes per locale
    [ ] Assistant answers re-checked in German and French

    Risks and how to handle them

    • Markets billed in USD by design

      Then keep USD but widen eligibleRegion so the plans are not shown as US-only.

    • hreflang errors across nine sites

      Generate clusters from one locale map in the CMS, not by hand.

    Evidence

    • Your websiteStructured data on the German pricing page de.squarespace.com/preise (fetched October 21, 2026): all eight plan offers are marked "priceCurrency":"USD" with "eligibleRegion" set to the Country "US", e.g. "Basic — Jährlich" at "228.00" USD; the page text shows "25 $ /Monat". The French /tarification page has the same eight US-only USD offers and shows "25 $US".Source
    • Your websiteLanguage versions (checked October 21, 2026): Squarespace runs translated sites at de., fr., es., pt., it., ja. and ko.squarespace.com, and the homepage declares them with 24 hreflang links. But in a random sample of 80 English sitemap pages (excluding offer and press-coverage pages), 76 carry no hreflang at all, including /pricing, /templates, every /compare page and the blog; the German /preise and /compare/jimdo pages and the French /tarification page carry none either. Only a few pages, such as the homepage, /ecommerce, /scheduling and /showcase, declare their translations.Source
    • HiringInternational Strategy and Marketing Lead (Dublin, posted September 4, 2026): owns "marketing and go-to-market strategy execution across our European markets, from research and insights to agency partnerships, content, AEO strategy, and channel development", with "a current focus on Germany and France"; asked to "unlock new channels and partners"; German or French fluency preferred.Source
    • HiringSenior Manager International Strategy (New York, posted September 3, 2026): owns GTM and "multi-year budgeting" for a portfolio of international markets, and will "Define and drive the content and AI-discovery strategy for owned markets, building the playbook that scales into new markets over time", plus media investment "tied to measurable performance outcomes".Source
  • 02

    Squarespace already has German comparison pages against Jimdo and IONOS and a page against the French builder e-monsite, but none declares its language alternates, and the international roles are asked to build an AEO playbook that scales market by market.

    High impactMedium effort First result in 1 quarter Senior Manager International…

    First action

    Pull current search impressions for the three pages by country.

    How to measure it

    Trial starts from local comparison pages

    Now
    –
    Target
    +30%
    By
    1 quarter

    Steps

    1. 1

      Baseline

      Impressions, clicks and trial starts per page.

      Senior Manager International Strategy 2 days

    2. 2

      Refresh facts

      Rival prices and features, dated.

      International Strategy and Marketing Lead 1 week

    3. 3

      Add quotable answers

      A 60-word summary at the top of each page.

      International Strategy and Marketing Lead 1 week

    4. 4

      Add local proof

      Two German and two French customer sites.

      International Strategy and Marketing Lead 2 weeks

    5. 5

      Promote

      Local agency placements and partner newsletters.

      International Strategy and Marketing Lead 1 month

    6. 6

      Write the playbook

      Turn what worked into the template for the next market.

      Senior Manager International Strategy 1 month

    First result
    1 quarter
    Cost
    Agency and translation time
    Owner
    Senior Manager International Strategy

    Smallest test

    Rewrite the German Jimdo page intro and track its clicks for a month.

    Why it works

    Treat these three as the pilot for the international AEO playbook: add hreflang, a dated comparison table with local prices and payment methods, a short answer paragraph at the top that assistants can quote, two local customer examples each, and a switching guide. Promote them through the local agencies the Dublin lead manages.

    Comparison searches are the highest-intent queries in a new market, and these rivals are the names local buyers already know.

    Risks and how to handle them

    • Rival facts go stale

      Date every table and review quarterly.

    Evidence

    • Your websiteSitemap (6,354 URLs): 4,044 /offers pages (sponsor offer pages such as /offers/libsynsports), of which 2,919 were last modified before 2023; 1,052 press-coverage pages; 866 blog posts; 70 solutions pages; 24 /compare pages, including Jimdo, IONOS and e-monsite as well as Wix, Hostinger, Framer, Lovable and Figma Sites; 15 free tools such as name generators.Source
    • Your websiteLanguage versions (checked October 21, 2026): Squarespace runs translated sites at de., fr., es., pt., it., ja. and ko.squarespace.com, and the homepage declares them with 24 hreflang links. But in a random sample of 80 English sitemap pages (excluding offer and press-coverage pages), 76 carry no hreflang at all, including /pricing, /templates, every /compare page and the blog; the German /preise and /compare/jimdo pages and the French /tarification page carry none either. Only a few pages, such as the homepage, /ecommerce, /scheduling and /showcase, declare their translations.Source
    • HiringInternational Strategy and Marketing Lead (Dublin, posted September 4, 2026): owns "marketing and go-to-market strategy execution across our European markets, from research and insights to agency partnerships, content, AEO strategy, and channel development", with "a current focus on Germany and France"; asked to "unlock new channels and partners"; German or French fluency preferred.Source
    • HiringSenior Manager International Strategy (New York, posted September 3, 2026): owns GTM and "multi-year budgeting" for a portfolio of international markets, and will "Define and drive the content and AI-discovery strategy for owned markets, building the playbook that scales into new markets over time", plus media investment "tied to measurable performance outcomes".Source
    • Competitor researchRivals' own homepages: Wix offers "2,000+ templates, built-in AI tools and a custom domain"; Framer calls itself an "AI design agent" that goes "from idea to launch"; Hostinger sells "Shared Hosting and Domains to VPS and Cloud plans"; Jimdo, a German builder, says "Bring Your Business Online".Source
  • 03

    The new growth marketing manager is asked to make the website "a highly optimized revenue driver" and "the front door to our brand". Real Chrome users wait 3.2 s for the homepage's main content and 282 ms for interactions at the 75th percentile, so it fails Core Web Vitals, and origin-wide LCP has slowed about 27% in a year. On a mid-range phone in Google's lab test the page weighs 8.2 MB and blocks the main thread for two seconds.

    High impactMedium effort First result in 1 month Senior Growth Marketing Manag…

    First action

    Run the PageSpeed report and list the five heaviest requests on the homepage.

    How to measure it

    Mobile homepage-to-trial rate

    Now
    –
    Target
    +8%
    By
    90 days

    Steps

    1. 1

      Set the budget

      LCP, INP and page-weight targets.

      Senior Growth Marketing Manager 1 day

    2. 2

      Find the weight

      Video, fonts, scripts and images by size.

      Web Engineering Lead 3 days

    3. 3

      Lighten the hero

      Poster image first, video after.

      Web Engineering Lead 1 week

    4. 4

      Defer scripts

      Tags and widgets after first interaction.

      Web Engineering Lead 1 week

    5. 5

      A/B test

      Light page vs current in Statsig.

      Senior Growth Marketing Manager 3 weeks

    6. 6

      Monitor real users

      Chrome UX Report monthly.

      Web Engineering Lead monthly

    First result
    1 month
    Cost
    Engineering time
    Owner
    Senior Growth Marketing Manager

    Smallest test

    Replace the hero video with a poster image for 10% of mobile visitors.

    Why it works

    Set a performance budget for the homepage and pricing page (LCP under 2.5 s and INP under 200 ms for real users), serve a poster image before the hero video, defer non-essential scripts until after interaction, cut the page weight in half, and A/B test the lighter page against the current one with trial starts as the metric.

    Faster pages convert better on mobile, and prospects judging a website builder notice when its own site is slow.

    Risks and how to handle them

    • Brand team wants the video

      Keep it, but load it after the poster.

    Evidence

    • PageSpeedGoogle PageSpeed for the homepage on mobile (October 21, 2026): lab performance score 27/100, Largest Contentful Paint 17.4 s, Total Blocking Time 2,020 ms and 8.2 MB transferred. Real Chrome users (Chrome UX Report) see LCP 3.2 s and Interaction to Next Paint 282 ms at the 75th percentile, both "needs improvement", so the page does not pass Core Web Vitals; across the whole origin LCP is 3.9 s and INP 302 ms, and origin LCP has slowed by about 27% over the past year. Layout shift passes.Source
    • HiringSenior Growth Marketing Manager (posted September 4, 2026): will "own web, lifecycle marketing and funnel conversion", own CAC, conversion, LTV and retention, "Ensure the website is a highly optimized revenue driver but also an incredible experience as the front door to our brand", build journeys "across email, SMS, in-app, and push", and run A/B testing; tools named include Amplitude, Iterable, Contentful and Statsig.Source
    • Your websiteHomepage: headline "A website makes it real"; "14M+ Entrepreneurs Served", "$36B+ Earned by Entrepreneurs", "200+" countries; "Start for free. No credit card required." The menu lists an AI Website Builder, Design Intelligence, Email and SMS Campaigns, SEO Tools, AI Visibility, Limited Releases, Financial Solutions, Domain Search and Business Email, plus Squarespace for Pros, the Circle partner program and Hire an Expert.Source
  • 04

    Basic is $19 a month billed annually with a 2% online store fee; Core is $29 with 0%. The $10 difference pays for itself at $500 a month in online sales, but the page leaves sellers to work that out, and the fee on digital content (7% vs 5%) adds another calculation.

    Medium impactLow effort First result in 3 weeks Senior Growth Marketing Manag…

    First action

    Write the formula and three seller examples.

    How to measure it

    Core-or-higher mix in new store subscriptions

    Now
    –
    Target
    +5 points
    By
    90 days

    Steps

    1. 1

      Agree the formula

      Fees, plan prices and payment rates.

      Senior Lead, AI Pricing & Margin Strategy 1 day

    2. 2

      Design

      One input row, one answer.

      Senior Product Designer 2 days

    3. 3

      Build

      On /pricing and every localized pricing page.

      Web Engineering Lead 1 week

    4. 4

      Preselect

      Recommended plan passed to checkout.

      Web Engineering Lead 2 days

    5. 5

      Test

      A/B against the current page.

      Senior Growth Marketing Manager 3 weeks

    6. 6

      Localize

      Same tool in German and French.

      International Strategy and Marketing Lead 2 weeks

    First result
    3 weeks
    Cost
    Engineering time
    Owner
    Senior Growth Marketing Manager

    Smallest test

    Add a static three-row example table first.

    Why it works

    Add a small calculator under the plan cards: monthly sales of products, services and digital content in, cheapest plan and yearly saving out. Pass the answer into checkout so the recommended plan is preselected.

    Showing the math turns a fee objection into a reason to upgrade, and sellers who choose the right plan churn less.

    Risks and how to handle them

    • Sellers anchor on the cheapest plan

      Show the yearly total at their sales level.

    Evidence

    • Your websitePricing page: "Free for 14 days", "Pay annually to save up to 36%". Basic $25 a month or $19 billed annually, with a 2% online store transaction fee and 7% on digital content and memberships; Core $39 or $29 annually with 0% store fee and 5% on digital content; Plus $65 or $49; Advanced $139 or $99. Core includes Google Workspace email free for the first year.Source
    • HiringSenior Growth Marketing Manager (posted September 4, 2026): will "own web, lifecycle marketing and funnel conversion", own CAC, conversion, LTV and retention, "Ensure the website is a highly optimized revenue driver but also an incredible experience as the front door to our brand", build journeys "across email, SMS, in-app, and push", and run A/B testing; tools named include Amplitude, Iterable, Contentful and Statsig.Source
  • 05

    Two-thirds of the sitemap is /offers pages, and 2,919 of the 4,044 were last modified before 2023. Many are likely for shows and campaigns that ended. The new GTM director is asked to "measure the direct business impact of marketing spend".

    Medium impactMedium effort First result in 1 month Director

    First action

    Export the offer pages with their last-modified date and match them to current contracts.

    How to measure it

    Sponsors with measured cost per customer

    Now
    –
    Target
    100% of live sponsors
    By
    1 quarter

    Steps

    1. 1

      Export

      Offer pages with dates.

      SEO Lead 1 day

    2. 2

      Match contracts

      Live vs ended sponsorships.

      Media Partnerships Manager 1 week

    3. 3

      Redirect

      Ended offers to the hub.

      SEO Lead 1 week

    4. 4

      Clean sitemaps

      All nine language sites.

      SEO Lead 2 days

    5. 5

      Tag the live ones

      Unique link and code per show.

      Media Partnerships Manager 2 weeks

    6. 6

      Report

      Cost per customer by show.

      Senior Manager, Data Science and Machine Learning monthly

    First result
    1 month
    Cost
    Staff time only
    Owner
    Director, GTM & Growth Marketing

    Smallest test

    Redirect the 100 oldest offer pages and watch crawl stats.

    Why it works

    Audit every offer page against active sponsorships. Redirect expired ones to a single live offers hub, remove them from the sitemap and all language versions, and give each live one a unique trial link and code mapped to its spend. Report cost per paying customer by show.

    Crawlers spend less time on dead pages, visitors stop landing on offers that no longer work, and the podcast budget gets a clear return figure.

    Risks and how to handle them

    • A partner still links to an old page

      The redirect sends their audience to a live offer.

    Evidence

    • Your websiteSitemap (6,354 URLs): 4,044 /offers pages (sponsor offer pages such as /offers/libsynsports), of which 2,919 were last modified before 2023; 1,052 press-coverage pages; 866 blog posts; 70 solutions pages; 24 /compare pages, including Jimdo, IONOS and e-monsite as well as Wix, Hostinger, Framer, Lovable and Figma Sites; 15 free tools such as name generators.Source
    • HiringDirector, GTM & Growth Marketing (posted September 15, 2026): will "build the overarching GTM playbook - defining the upstream briefs, channel strategies, financial models, and feedback loops", act as the main GTM contact for product GMs "across a growing portfolio", "measure the direct business impact of marketing spend" and "Build post-launch feedback loops that actively inform the next brief".Source
    • HiringAlso open: a Senior Manager, Data Science and Machine Learning (posted October 13, 2026) leading a team of 12 on "marketing measurement, sales growth, product optimization" with "causal inference frameworks"; and a Director, Corporate Communications (posted October 5, 2026) to "Develop and maintain a consistent narrative that works across both consumer and B2B audiences" and run communications "in select jurisdictions outside the United States".Source
  • 06

    Squarespace has 15 free tools, mostly name generators, and each ends with generic links to "register a domain", "start a free website trial" or "use our logo maker". The visitor has to retype the name they just chose.

    Medium impactLow effort First result in 1 month Senior Growth Marketing Manag…

    First action

    Measure today's click rate from tool results to domain search.

    How to measure it

    Tool-to-domain conversion

    Now
    –
    Target
    2x
    By
    60 days

    Steps

    1. 1

      Baseline

      Clicks from tools to domains and trials.

      Senior Growth Marketing Manager 2 days

    2. 2

      Add availability

      Check each generated name.

      Web Engineering Lead 1 week

    3. 3

      Pass the name

      Into trial and cart.

      Web Engineering Lead 1 week

    4. 4

      Test

      Against the current pages.

      Senior Growth Marketing Manager 3 weeks

    5. 5

      Extend

      All 15 tools and locales.

      Web Engineering Lead 1 month

    6. 6

      Report

      Domains and trials by tool.

      Head of Domains & Email monthly

    First result
    1 month
    Cost
    Engineering time
    Owner
    Senior Growth Marketing Manager

    Smallest test

    Add availability to the online store name generator only.

    Why it works

    Show live domain availability next to each generated name, and make "Use this name" open a trial with the name already set as the site title and the domain in the cart.

    The moment someone picks a name is the moment they are most likely to register it, and the domain business is run as its own P&L.

    Risks and how to handle them

    • Too many taken names

      Suggest close variants and other extensions.

    Evidence

    • Your websiteFree tool pages such as the Online Store Name Generator end with three generic next steps, "register a domain", "start a free website trial" or "use our logo maker", rather than carrying the generated name into a domain check or a trial.Source
    • Your websiteSitemap (6,354 URLs): 4,044 /offers pages (sponsor offer pages such as /offers/libsynsports), of which 2,919 were last modified before 2023; 1,052 press-coverage pages; 866 blog posts; 70 solutions pages; 24 /compare pages, including Jimdo, IONOS and e-monsite as well as Wix, Hostinger, Framer, Lovable and Figma Sites; 15 free tools such as name generators.Source
    • HiringHead of Domains & Email (reports to the President): runs Domains and Email "as a business within a business" with the P&L; Squarespace calls itself "one of the world's largest domain providers"; the role owns "pricing, packaging, acquisition, retention, and expansion — including cross-sell and upsell into adjacent Squarespace products", and says "AI is fundamentally reshaping how people discover, register, manage, and derive value from domain names".Source

This quarter 10

The core plays for the next three months.

  • 07

    The Head of Domains & Email owns cross-sell "into adjacent Squarespace products", and Squarespace calls itself one of the world's largest domain providers. Customers who own a domain but no Squarespace site are the warmest audience for a website plan.

    High impactMedium effort First result in 1 quarter Head of Domains & Email

    First action

    Count domain-only accounts by age and renewal date.

    How to measure it

    Domain-to-site conversion

    Now
    –
    Target
    +3 points
    By
    2 quarters

    Steps

    1. 1

      Size the base

      Domain-only accounts by segment.

      Head of Domains & Email 1 week

    2. 2

      Build the draft

      AI site from the domain name.

      Product Manager, AI Builder 1 month

    3. 3

      Write the email

      Preview link and offer.

      Senior Product Director, Client Engagement Group 1 week

    4. 4

      Test

      10% of accounts at renewal.

      Head of Domains & Email 1 month

    5. 5

      Add in dashboard

      Preview card in the domain panel.

      Head of Domains & Email 1 month

    6. 6

      Measure

      Publishes and retention.

      Senior Manager, Data Science and Machine Learning monthly

    First result
    1 quarter
    Cost
    Product time and discounts
    Owner
    Head of Domains & Email

    Smallest test

    Send 1,000 previews to domain-only customers near renewal.

    Why it works

    For domain-only accounts, generate a draft site with the AI builder from the domain name and any existing DNS clues, and send it as "your domain, already live as a preview". Offer the first month of Core at a discount when they publish.

    Showing a finished draft removes the blank-page problem, and the customer already trusts Squarespace with the domain.

    Risks and how to handle them

    • Customers who use the domain elsewhere

      Exclude domains already pointing at a live site.

    Evidence

    • HiringHead of Domains & Email (reports to the President): runs Domains and Email "as a business within a business" with the P&L; Squarespace calls itself "one of the world's largest domain providers"; the role owns "pricing, packaging, acquisition, retention, and expansion — including cross-sell and upsell into adjacent Squarespace products", and says "AI is fundamentally reshaping how people discover, register, manage, and derive value from domain names".Source
    • Your websiteNew AI products: Forma is "an AI app builder that turns simple prompts into fully functional, custom apps and websites, no code required" with a waitlist; the AI Visibility page invites owners to "see how your brand appears in AI summaries"; the blog covers the Blueprint AI website builder and the Image Studio AI image generator (both October 2026 posts).Source
    • Your websiteHomepage: headline "A website makes it real"; "14M+ Entrepreneurs Served", "$36B+ Earned by Entrepreneurs", "200+" countries; "Start for free. No credit card required." The menu lists an AI Website Builder, Design Intelligence, Email and SMS Campaigns, SEO Tools, AI Visibility, Limited Releases, Financial Solutions, Domain Search and Business Email, plus Squarespace for Pros, the Circle partner program and Hire an Expert.Source
  • 08

    The Client Engagement Group is told its tools are "a critical lever in increasing product attach, reducing merchant churn" and owns Email Campaigns end to end.

    High impactMedium effort First result in 1 quarter Senior Product Director

    First action

    Pull retention for sellers with and without Email Campaigns.

    How to measure it

    Attach in first 90 days

    Now
    –
    Target
    +20%
    By
    2 quarters

    Steps

    1. 1

      Find milestones

      From retained cohorts.

      Senior Manager, Data Science and Machine Learning 2 weeks

    2. 2

      Draft campaigns

      Templates per milestone.

      Senior Product Director, Client Engagement Group 2 weeks

    3. 3

      Build prompts

      In the dashboard and app.

      Senior Product Director, Client Engagement Group 1 month

    4. 4

      Add SMS

      For sellers with phone numbers.

      Senior Product Director, Client Engagement Group 1 month

    5. 5

      Test

      Holdout group.

      Senior Manager, Data Science and Machine Learning 1 quarter

    6. 6

      Report

      Attach and churn.

      Senior Product Director, Client Engagement Group monthly

    First result
    1 quarter
    Cost
    Product time
    Owner
    Senior Product Director, Client Engagement Group

    Smallest test

    Trigger the first-sale campaign for one week of new sellers.

    Why it works

    Trigger an in-dashboard prompt with a ready-made campaign at three milestones: the first order, the first Acuity booking and the 100th contact. Each draft uses the seller's products and branding and sends with one click.

    Sellers adopt marketing tools when they have someone to market to, and every attached product lowers churn.

    Risks and how to handle them

    • Prompt fatigue

      One prompt per milestone, easy to dismiss.

    Evidence

    • HiringSenior Product Director, Client Engagement Group (posted September 10, 2026): leads "the CRM, email campaigns, automations, and transactional communications"; "Our marketing tools are a critical lever in increasing product attach, reducing merchant churn"; owns "the Email Campaigns business line end-to-end", including SMS.Source
    • HiringSenior Product Manager, Acuity Scheduling, Payments (posted September 25, 2026): "Payments is central to that value proposition, and it's one of Acuity's most significant growth opportunities"; the role builds "the payment experiences, defaults, and integrations that make on-platform collection the obvious choice" and is asked to "accelerate GPV growth".Source
    • HiringSenior Growth Marketing Manager (posted September 4, 2026): will "own web, lifecycle marketing and funnel conversion", own CAC, conversion, LTV and retention, "Ensure the website is a highly optimized revenue driver but also an incredible experience as the front door to our brand", build journeys "across email, SMS, in-app, and push", and run A/B testing; tools named include Amplitude, Iterable, Contentful and Statsig.Source
  • 09

    The AI pricing lead will design "credit and usage-based pricing models" and launch incentives for new AI features, while Forma has a waitlist and Squarespace already ships Blueprint, Design Intelligence and Image Studio. Buyers compare AI builders on what is included.

    High impactMedium effort First result in 1 quarter Senior Lead

    First action

    List every AI feature and its current limit.

    How to measure it

    Forma waitlist conversion

    Now
    –
    Target
    15%
    By
    2 quarters

    Steps

    1. 1

      Inventory features

      Every AI feature and limit.

      Senior Lead, AI Pricing & Margin Strategy 1 week

    2. 2

      Model credits

      Cost and margin per action.

      Senior Lead, AI Pricing & Margin Strategy 1 month

    3. 3

      Write the page

      Plans, credits, overages.

      Product Marketing Manager 2 weeks

    4. 4

      Launch pack

      For waitlist members.

      Senior Lead, AI Pricing & Margin Strategy 2 weeks

    5. 5

      Localize

      All language sites.

      International Strategy and Marketing Lead 2 weeks

    6. 6

      Track

      Conversion and overage complaints.

      Senior Manager, Data Science and Machine Learning monthly

    First result
    1 quarter
    Cost
    Staff time
    Owner
    Senior Lead, AI Pricing & Margin Strategy

    Smallest test

    Publish the credits table for existing AI features first.

    Why it works

    Publish a single page that lists what each plan includes in AI credits, what each feature costs in credits, and what happens at the limit. Give waitlist members a launch credit pack and track who converts.

    Clear limits build trust and stop surprise bills from becoming churn, and a launch pack gives the waitlist a reason to act.

    Risks and how to handle them

    • Margins change with model prices

      Review credit costs quarterly.

    Evidence

    • HiringSenior Lead, AI Pricing & Margin Strategy (posted September 22, 2026): will "Design and evaluate customer-facing credit and usage-based pricing models, including tier structures, usage limits, and overage mechanics", translate AI usage "into credit equivalents" and "Structure promotional offers and launch incentives for new AI features".Source
    • Your websiteNew AI products: Forma is "an AI app builder that turns simple prompts into fully functional, custom apps and websites, no code required" with a waitlist; the AI Visibility page invites owners to "see how your brand appears in AI summaries"; the blog covers the Blueprint AI website builder and the Image Studio AI image generator (both October 2026 posts).Source
    • Your websitePricing page: "Free for 14 days", "Pay annually to save up to 36%". Basic $25 a month or $19 billed annually, with a 2% online store transaction fee and 7% on digital content and memberships; Core $39 or $29 annually with 0% store fee and 5% on digital content; Plus $65 or $49; Advanced $139 or $99. Core includes Google Workspace email free for the first year.Source
  • 10

    The mobile role says sellers "increasingly run their businesses from their phones" and mobile should become "a primary growth channel", measured on seller activation.

    High impactHigh effort First result in 2 quarters Senior Director of Product

    First action

    Measure today's mobile sign-up to first-payment rate.

    How to measure it

    Mobile first-payment rate

    Now
    –
    Target
    +25%
    By
    2 quarters

    Steps

    1. 1

      Map the path

      Every step from sign-up to payment.

      Senior Director of Product, Mobile 2 weeks

    2. 2

      Cut steps

      One-page site and payment link first.

      Senior Director of Product, Mobile 1 month

    3. 3

      Build

      App and mobile web.

      Mobile Engineering Lead 1 quarter

    4. 4

      Test

      Share of mobile sign-ups.

      Senior Director of Product, Mobile 1 month

    5. 5

      Connect lifecycle

      Push and email nudges.

      Senior Growth Marketing Manager 2 weeks

    6. 6

      Measure

      Activation by device.

      Senior Manager, Data Science and Machine Learning monthly

    First result
    2 quarters
    Cost
    Product time
    Owner
    Senior Director of Product, Mobile

    Smallest test

    Test a payment-link-first flow with 5% of mobile sign-ups.

    Why it works

    Build a mobile onboarding that gets a new seller from sign-up to a published one-page site, a payment link and an invoice in under ten minutes on a phone. Track activation against desktop sign-ups.

    Many small sellers never open a laptop for their business, and the first payment is the strongest activation signal.

    Risks and how to handle them

    • Thin sites on mobile

      Offer the full editor once the seller is paid.

    Evidence

    • HiringSenior Director of Product, Mobile (posted September 17, 2026): mobile is evolving "from a companion to desktop into a primary growth channel"; "Sellers increasingly run their businesses from their phones, taking payments in person, sending invoices, and managing orders on the go"; measured on "seller activation, engagement, and revenue".Source
    • Your websitePricing page: "Free for 14 days", "Pay annually to save up to 36%". Basic $25 a month or $19 billed annually, with a 2% online store transaction fee and 7% on digital content and memberships; Core $39 or $29 annually with 0% store fee and 5% on digital content; Plus $65 or $49; Advanced $139 or $99. Core includes Google Workspace email free for the first year.Source
    • HiringSenior Product Manager, Acuity Scheduling, Payments (posted September 25, 2026): "Payments is central to that value proposition, and it's one of Acuity's most significant growth opportunities"; the role builds "the payment experiences, defaults, and integrations that make on-platform collection the obvious choice" and is asked to "accelerate GPV growth".Source
  • 11

    Acuity's payments role is asked to build "defaults" that "make on-platform collection the obvious choice" and to grow payment volume. Beauty and health businesses are a core Squarespace segment and lose money to no-shows.

    High impactMedium effort First result in 1 quarter Senior Product Manager

    First action

    Compare no-show rates for Acuity businesses with and without deposits.

    How to measure it

    Payment-enabled appointment types

    Now
    –
    Target
    +15 points
    By
    2 quarters

    Steps

    1. 1

      Measure no-shows

      With and without deposits.

      Senior Manager, Data Science and Machine Learning 2 weeks

    2. 2

      Design the default

      Segment and amount.

      Senior Product Manager, Acuity Scheduling, Payments 1 week

    3. 3

      Build

      Default and explainer.

      Senior Product Manager, Acuity Scheduling, Payments 1 month

    4. 4

      Test

      New accounts in two segments.

      Senior Product Manager, Acuity Scheduling, Payments 1 month

    5. 5

      Report to owners

      No-shows avoided.

      Senior Product Manager, Acuity Scheduling, Payments 1 month

    6. 6

      Roll out

      Other segments.

      Senior Product Manager, Acuity Scheduling, Payments 1 quarter

    First result
    1 quarter
    Cost
    Product time
    Owner
    Senior Product Manager, Acuity Scheduling, Payments

    Smallest test

    Turn the default on for new hair salon accounts.

    Why it works

    When a beauty or wellness business creates a new appointment type, preselect a deposit (for example 20%) with a short note on no-show savings. Show each business its no-shows avoided each month.

    Defaults drive adoption, and deposits pay for themselves in fewer empty slots.

    Risks and how to handle them

    • Clients dislike deposits

      Let businesses switch it off in one click.

    Evidence

    • HiringSenior Product Manager, Acuity Scheduling, Payments (posted September 25, 2026): "Payments is central to that value proposition, and it's one of Acuity's most significant growth opportunities"; the role builds "the payment experiences, defaults, and integrations that make on-platform collection the obvious choice" and is asked to "accelerate GPV growth".Source
    • Your websiteHomepage: headline "A website makes it real"; "14M+ Entrepreneurs Served", "$36B+ Earned by Entrepreneurs", "200+" countries; "Start for free. No credit card required." The menu lists an AI Website Builder, Design Intelligence, Email and SMS Campaigns, SEO Tools, AI Visibility, Limited Releases, Financial Solutions, Domain Search and Business Email, plus Squarespace for Pros, the Circle partner program and Hire an Expert.Source
  • 12

    The data science team is hired for "marketing measurement" with "causal inference frameworks", and Squarespace spends heavily on brand moments such as its Super Bowl LX campaign and on podcast sponsorships.

    High impactHigh effort First result in 2 quarters Senior Manager

    First action

    Pick ten matched market pairs.

    How to measure it

    Channels with incrementality reads

    Now
    –
    Target
    3
    By
    2 quarters

    Steps

    1. 1

      Pick markets

      Matched pairs by history.

      Senior Manager, Data Science and Machine Learning 2 weeks

    2. 2

      Plan spend

      Pause and boost cells.

      Media Director 2 weeks

    3. 3

      Run

      Six-week test.

      Media Director 6 weeks

    4. 4

      Analyze

      Trials and paid conversions.

      Senior Manager, Data Science and Machine Learning 2 weeks

    5. 5

      Brief

      Results into GTM briefs.

      Director, GTM & Growth Marketing 1 week

    6. 6

      Repeat

      Each half year.

      Senior Manager, Data Science and Machine Learning 6 months

    First result
    2 quarters
    Cost
    Lost reach in holdout markets
    Owner
    Senior Manager, Data Science and Machine Learning

    Smallest test

    Run one podcast holdout in two markets.

    Why it works

    Run matched-market holdouts: pause or double podcast and connected-TV spend in comparable regions for six weeks and measure trial starts and paid conversions. Use the results to set the media mix in the GTM briefs.

    Holdouts show what attribution cannot, and they give the new GTM director a defensible budget split.

    Risks and how to handle them

    • Seasonality

      Use matched controls and two years of history.

    Evidence

    • HiringAlso open: a Senior Manager, Data Science and Machine Learning (posted October 13, 2026) leading a team of 12 on "marketing measurement, sales growth, product optimization" with "causal inference frameworks"; and a Director, Corporate Communications (posted October 5, 2026) to "Develop and maintain a consistent narrative that works across both consumer and B2B audiences" and run communications "in select jurisdictions outside the United States".Source
    • Press releasesSquarespace press releases: "Permira Completes Acquisition of Squarespace" (October 2024); "Squarespace and Perplexity Partner to Reimagine Business Creation in the AI Era" (October 2025); a Super Bowl LX campaign with Emma Stone on "the Stakes of Domain Ownership" (February 2026); "Squarespace Balance" for business finances (March 2026); tools for "Selling in Limited Releases and Drops" (July 2026).Source
    • HiringDirector, GTM & Growth Marketing (posted September 15, 2026): will "build the overarching GTM playbook - defining the upstream briefs, channel strategies, financial models, and feedback loops", act as the main GTM contact for product GMs "across a growing portfolio", "measure the direct business impact of marketing spend" and "Build post-launch feedback loops that actively inform the next brief".Source
    • Your websiteSitemap (6,354 URLs): 4,044 /offers pages (sponsor offer pages such as /offers/libsynsports), of which 2,919 were last modified before 2023; 1,052 press-coverage pages; 866 blog posts; 70 solutions pages; 24 /compare pages, including Jimdo, IONOS and e-monsite as well as Wix, Hostinger, Framer, Lovable and Figma Sites; 15 free tools such as name generators.Source
  • 13

    The GTM director will build "upstream briefs, channel strategies, financial models, and feedback loops" across a growing portfolio. Forma, an AI app builder with a waitlist, is the next big launch.

    High impactMedium effort First result in 1 quarter Director

    First action

    Draft the one-page Forma brief.

    How to measure it

    Forma 90-day paid sign-ups vs brief

    Now
    –
    Target
    100% of target
    By
    2 quarters

    Steps

    1. 1

      Write the brief

      Segments, channels, model.

      Director, GTM & Growth Marketing 2 weeks

    2. 2

      Align GMs

      Targets and trade-offs.

      Director, GTM & Growth Marketing 1 week

    3. 3

      Comparison pages

      Against Lovable and Framer, refreshed.

      Product Marketing Manager 2 weeks

    4. 4

      Launch

      Waitlist first, then paid media.

      Senior Growth Marketing Manager 1 month

    5. 5

      Review at 30 days

      What to change.

      Director, GTM & Growth Marketing 1 day

    6. 6

      Feed the next brief

      Lessons into the template.

      Director, GTM & Growth Marketing 1 week

    First result
    1 quarter
    Cost
    Launch budget
    Owner
    Director, GTM & Growth Marketing

    Smallest test

    Write the brief and share it with two GMs.

    Why it works

    Write Forma's brief in the new format: target segments, channel plan, financial model, local versions, and a post-launch review at 30 and 90 days. Use the waitlist as the first audience and compare against prior launches.

    A real launch proves the playbook faster than a framework document, and Forma faces fast-moving AI builder rivals.

    Risks and how to handle them

    • Launch slips

      Keep the brief and review dates anyway.

    Evidence

    • HiringDirector, GTM & Growth Marketing (posted September 15, 2026): will "build the overarching GTM playbook - defining the upstream briefs, channel strategies, financial models, and feedback loops", act as the main GTM contact for product GMs "across a growing portfolio", "measure the direct business impact of marketing spend" and "Build post-launch feedback loops that actively inform the next brief".Source
    • Your websiteNew AI products: Forma is "an AI app builder that turns simple prompts into fully functional, custom apps and websites, no code required" with a waitlist; the AI Visibility page invites owners to "see how your brand appears in AI summaries"; the blog covers the Blueprint AI website builder and the Image Studio AI image generator (both October 2026 posts).Source
    • Competitor researchRivals' own homepages: Wix offers "2,000+ templates, built-in AI tools and a custom domain"; Framer calls itself an "AI design agent" that goes "from idea to launch"; Hostinger sells "Shared Hosting and Domains to VPS and Cloud plans"; Jimdo, a German builder, says "Bring Your Business Online".Source
    • Your websiteSitemap (6,354 URLs): 4,044 /offers pages (sponsor offer pages such as /offers/libsynsports), of which 2,919 were last modified before 2023; 1,052 press-coverage pages; 866 blog posts; 70 solutions pages; 24 /compare pages, including Jimdo, IONOS and e-monsite as well as Wix, Hostinger, Framer, Lovable and Figma Sites; 15 free tools such as name generators.Source
  • 14

    The Dublin lead is asked to "unlock new channels and partners". Squarespace already runs Circle for freelancers and agencies and has a German Circle page, but local designers in Germany and France are not yet a visible channel.

    Medium impactMedium effort First result in 2 quarters International Strategy and Ma…

    First action

    List 100 German and French designers already building on Squarespace.

    How to measure it

    Partner-built sites in DE and FR

    Now
    –
    Target
    500
    By
    2 quarters

    Steps

    1. 1

      Find designers

      Existing users with client sites.

      International Strategy and Marketing Lead 2 weeks

    2. 2

      Local offer

      Onboarding and referral share.

      International Strategy and Marketing Lead 2 weeks

    3. 3

      Events

      Meetups in Berlin and Paris.

      International Strategy and Marketing Lead 1 quarter

    4. 4

      List in Hire an Expert

      Filter by language.

      Partner Programs Manager 1 month

    5. 5

      Support

      German and French partner support.

      Customer Operations Lead 1 month

    6. 6

      Measure

      Sites and revenue by partner.

      Senior Manager International Strategy monthly

    First result
    2 quarters
    Cost
    Events and referral payments
    Owner
    International Strategy and Marketing Lead

    Smallest test

    Host one partner evening in Berlin.

    Why it works

    Recruit 50 web designers in each country through local design schools, meetups and agencies, offer them local-language onboarding and a referral share, and list them in Hire an Expert by language. Track the sites they launch.

    Designers bring clients and local credibility in markets where rivals such as Jimdo and IONOS are familiar names.

    Risks and how to handle them

    • Partners prefer WordPress

      Lead with speed of delivery and client editing.

    Evidence

    • HiringInternational Strategy and Marketing Lead (Dublin, posted September 4, 2026): owns "marketing and go-to-market strategy execution across our European markets, from research and insights to agency partnerships, content, AEO strategy, and channel development", with "a current focus on Germany and France"; asked to "unlock new channels and partners"; German or French fluency preferred.Source
    • Your websiteThe Circle partner program page ("Join Squarespace Circle to unlock exclusive benefits and resources to scale your business") exists in German at de.squarespace.com/circle, also without hreflang.Source
    • Your websiteHomepage: headline "A website makes it real"; "14M+ Entrepreneurs Served", "$36B+ Earned by Entrepreneurs", "200+" countries; "Start for free. No credit card required." The menu lists an AI Website Builder, Design Intelligence, Email and SMS Campaigns, SEO Tools, AI Visibility, Limited Releases, Financial Solutions, Domain Search and Business Email, plus Squarespace for Pros, the Circle partner program and Hire an Expert.Source
    • Competitor researchRivals' own homepages: Wix offers "2,000+ templates, built-in AI tools and a custom domain"; Framer calls itself an "AI design agent" that goes "from idea to launch"; Hostinger sells "Shared Hosting and Domains to VPS and Cloud plans"; Jimdo, a German builder, says "Bring Your Business Online".Source
  • 15

    The trial is free for 14 days with no card, and the growth marketing manager owns lifecycle and funnel conversion with tools such as Iterable and Amplitude.

    High impactMedium effort First result in 1 quarter Senior Growth Marketing Manag…

    First action

    List the five actions that best predict trial conversion.

    How to measure it

    Trial conversion

    Now
    –
    Target
    +10%
    By
    2 quarters

    Steps

    1. 1

      Find predictors

      Actions in converted trials.

      Senior Manager, Data Science and Machine Learning 2 weeks

    2. 2

      Write emails

      One per missing step.

      Senior Growth Marketing Manager 2 weeks

    3. 3

      Build triggers

      In Iterable.

      Senior Growth Marketing Manager 2 weeks

    4. 4

      Add in-app

      Same prompts in the editor.

      Senior Growth Marketing Manager 2 weeks

    5. 5

      Test

      Against the current series.

      Senior Growth Marketing Manager 1 month

    6. 6

      Localize

      All language sites.

      International Strategy and Marketing Lead 1 month

    First result
    1 quarter
    Cost
    Staff time
    Owner
    Senior Growth Marketing Manager

    Smallest test

    Test the "no domain chosen" email alone.

    Why it works

    Replace time-based trial emails with behavior-based ones: no domain chosen, no page edited, no product added, no payment set up. Each email links straight to the missing step, and day 12 offers help from an Expert for sites that are nearly ready.

    People convert when they reach a working site, and each message removes the one obstacle in front of them.

    Risks and how to handle them

    • Too many emails

      Cap at one a day.

    Evidence

    • Your websitePricing page: "Free for 14 days", "Pay annually to save up to 36%". Basic $25 a month or $19 billed annually, with a 2% online store transaction fee and 7% on digital content and memberships; Core $39 or $29 annually with 0% store fee and 5% on digital content; Plus $65 or $49; Advanced $139 or $99. Core includes Google Workspace email free for the first year.Source
    • HiringSenior Growth Marketing Manager (posted September 4, 2026): will "own web, lifecycle marketing and funnel conversion", own CAC, conversion, LTV and retention, "Ensure the website is a highly optimized revenue driver but also an incredible experience as the front door to our brand", build journeys "across email, SMS, in-app, and push", and run A/B testing; tools named include Amplitude, Iterable, Contentful and Statsig.Source
    • Your websiteHomepage: headline "A website makes it real"; "14M+ Entrepreneurs Served", "$36B+ Earned by Entrepreneurs", "200+" countries; "Start for free. No credit card required." The menu lists an AI Website Builder, Design Intelligence, Email and SMS Campaigns, SEO Tools, AI Visibility, Limited Releases, Financial Solutions, Domain Search and Business Email, plus Squarespace for Pros, the Circle partner program and Hire an Expert.Source
  • 16

    Squarespace sells an AI Visibility tool that shows "how your brand appears in AI summaries", and its international team is building an AI-discovery playbook.

    Medium impactLow effort First result in 1 quarter Senior Manager International…

    First action

    Write 20 buyer questions per market.

    How to measure it

    AI answer share in DE and FR

    Now
    –
    Target
    +10 points
    By
    2 quarters

    Steps

    1. 1

      Write questions

      20 per market.

      International Strategy and Marketing Lead 1 week

    2. 2

      Baseline

      Run the tool.

      Senior Manager International Strategy 1 week

    3. 3

      Fix gaps

      Content and markup.

      SEO Lead 1 quarter

    4. 4

      Monthly re-run

      Scorecard.

      Senior Manager International Strategy monthly

    5. 5

      Case study

      For customers.

      Product Marketing Manager 1 month

    6. 6

      Scale

      Next markets.

      Senior Manager International Strategy 1 quarter

    First result
    1 quarter
    Cost
    Staff time
    Owner
    Senior Manager International Strategy

    Smallest test

    Run ten German questions this week.

    Why it works

    Track a fixed set of buyer questions per market ("best website builder for photographers", "Squarespace vs Jimdo") in each language every month. Publish an internal scorecard and use it to prioritize content and fixes, then turn the method into a case study for customers.

    It gives the international team a baseline at no cost and shows customers the tool works.

    Risks and how to handle them

    • Answers vary run to run

      Average several runs per question.

    Evidence

    • Your websiteNew AI products: Forma is "an AI app builder that turns simple prompts into fully functional, custom apps and websites, no code required" with a waitlist; the AI Visibility page invites owners to "see how your brand appears in AI summaries"; the blog covers the Blueprint AI website builder and the Image Studio AI image generator (both October 2026 posts).Source
    • HiringSenior Manager International Strategy (New York, posted September 3, 2026): owns GTM and "multi-year budgeting" for a portfolio of international markets, and will "Define and drive the content and AI-discovery strategy for owned markets, building the playbook that scales into new markets over time", plus media investment "tied to measurable performance outcomes".Source
    • HiringInternational Strategy and Marketing Lead (Dublin, posted September 4, 2026): owns "marketing and go-to-market strategy execution across our European markets, from research and insights to agency partnerships, content, AEO strategy, and channel development", with "a current focus on Germany and France"; asked to "unlock new channels and partners"; German or French fluency preferred.Source

Big bets 3

Larger plays that can change the trajectory.

  • 17

    Squarespace says it has served 14M+ entrepreneurs who earned $36B+, and already writes about business survival rates by industry. The new communications director must tell one story to consumer and B2B audiences and run communications outside the US.

    High impactHigh effort First result in 3 quarters Director

    First action

    Pick ten questions reporters ask about small businesses.

    How to measure it

    Earned media pieces per edition

    Now
    –
    Target
    100
    By
    1 year

    Steps

    1. 1

      Pick questions

      Ten reporter questions.

      Director, Corporate Communications 2 weeks

    2. 2

      Build the data

      Aggregated and anonymized.

      Senior Manager, Data Science and Machine Learning 2 months

    3. 3

      Privacy review

      No seller identifiable.

      Legal 1 month

    4. 4

      Write editions

      US, UK, DE, FR.

      Director, Corporate Communications 1 month

    5. 5

      Launch

      Press and social.

      Director, Corporate Communications 1 month

    6. 6

      Repeat

      Every six months.

      Director, Corporate Communications 6 months

    First result
    3 quarters
    Cost
    Analyst and PR time
    Owner
    Director, Corporate Communications

    Smallest test

    Publish one chart on new business launches by industry.

    Why it works

    Publish an aggregated index of new small-business launches, online sales and bookings by industry and country, with local editions for the UK, Germany and France. Give reporters charts, and give AI assistants a citable source.

    Original data earns coverage and links in every market and makes Squarespace the source on small business online.

    Risks and how to handle them

    • Data privacy

      Aggregate and suppress small groups.

    Evidence

    • Your websiteHomepage: headline "A website makes it real"; "14M+ Entrepreneurs Served", "$36B+ Earned by Entrepreneurs", "200+" countries; "Start for free. No credit card required." The menu lists an AI Website Builder, Design Intelligence, Email and SMS Campaigns, SEO Tools, AI Visibility, Limited Releases, Financial Solutions, Domain Search and Business Email, plus Squarespace for Pros, the Circle partner program and Hire an Expert.Source
    • HiringAlso open: a Senior Manager, Data Science and Machine Learning (posted October 13, 2026) leading a team of 12 on "marketing measurement, sales growth, product optimization" with "causal inference frameworks"; and a Director, Corporate Communications (posted October 5, 2026) to "Develop and maintain a consistent narrative that works across both consumer and B2B audiences" and run communications "in select jurisdictions outside the United States".Source
    • HiringSenior Manager International Strategy (New York, posted September 3, 2026): owns GTM and "multi-year budgeting" for a portfolio of international markets, and will "Define and drive the content and AI-discovery strategy for owned markets, building the playbook that scales into new markets over time", plus media investment "tied to measurable performance outcomes".Source
  • 18

    The Head of Domains says AI is reshaping how people "discover, register, manage" domains, and Squarespace has partnered with Perplexity on business creation.

    High impactHigh effort First result in 4 quarters Head of Domains & Email

    First action

    Map how assistants answer "help me name and register my business" today.

    How to measure it

    Assistant-sourced registrations

    Now
    –
    Target
    50,000
    By
    4 quarters

    Steps

    1. 1

      Map today

      Assistant answers by market.

      Head of Domains & Email 2 weeks

    2. 2

      Design flow

      Name, check, register, draft.

      Head of Domains & Email 1 month

    3. 3

      Build APIs

      Availability and checkout links.

      Domains Engineering Lead 1 quarter

    4. 4

      Pilot

      With the existing partner.

      Head of Domains & Email 1 quarter

    5. 5

      Add sites

      Draft website on registration.

      Product Manager, AI Builder 1 quarter

    6. 6

      Measure

      Registrations and site attach.

      Senior Manager, Data Science and Machine Learning monthly

    First result
    4 quarters
    Cost
    Engineering and partnership time
    Owner
    Head of Domains & Email

    Smallest test

    Prototype the flow for one assistant.

    Why it works

    Build an assistant-facing flow: a person describes their business, gets available names with prices, and registers one with a draft site attached, completing payment on Squarespace. Start with the existing partnership and add other assistants.

    The first step of a new business is moving into AI chats, and whoever registers the domain there usually gets the website.

    Risks and how to handle them

    • Assistants change their rules

      Keep the flow standard and portable.

    Evidence

    • HiringHead of Domains & Email (reports to the President): runs Domains and Email "as a business within a business" with the P&L; Squarespace calls itself "one of the world's largest domain providers"; the role owns "pricing, packaging, acquisition, retention, and expansion — including cross-sell and upsell into adjacent Squarespace products", and says "AI is fundamentally reshaping how people discover, register, manage, and derive value from domain names".Source
    • Press releasesSquarespace press releases: "Permira Completes Acquisition of Squarespace" (October 2024); "Squarespace and Perplexity Partner to Reimagine Business Creation in the AI Era" (October 2025); a Super Bowl LX campaign with Emma Stone on "the Stakes of Domain Ownership" (February 2026); "Squarespace Balance" for business finances (March 2026); tools for "Selling in Limited Releases and Drops" (July 2026).Source
    • Your websiteNew AI products: Forma is "an AI app builder that turns simple prompts into fully functional, custom apps and websites, no code required" with a waitlist; the AI Visibility page invites owners to "see how your brand appears in AI summaries"; the blog covers the Blueprint AI website builder and the Image Studio AI image generator (both October 2026 posts).Source
  • 19

    Squarespace launched tools for "Selling in Limited Releases and Drops", and the mobile role highlights in-person payments as a growth driver.

    Medium impactHigh effort First result in 3 quarters Senior Director of Product

    First action

    Interview 20 sellers who used limited releases.

    How to measure it

    Drop GPV

    Now
    –
    Target
    +50%
    By
    3 quarters

    Steps

    1. 1

      Interview sellers

      Pain points at drops.

      Senior Director of Product, Mobile 2 weeks

    2. 2

      Design kit

      Release, in-person, SMS.

      Senior Director of Product, Mobile 1 month

    3. 3

      Build

      Shared inventory and app flow.

      Mobile Engineering Lead 1 quarter

    4. 4

      Pilot

      100 sellers.

      Senior Director of Product, Mobile 1 quarter

    5. 5

      Market

      Maker and apparel channels.

      Senior Growth Marketing Manager 1 month

    6. 6

      Measure

      GPV and retention.

      Senior Manager, Data Science and Machine Learning monthly

    First result
    3 quarters
    Cost
    Product time
    Owner
    Senior Director of Product, Mobile

    Smallest test

    Run one pilot pop-up with five sellers.

    Why it works

    Package a drop kit: schedule a release, sell online and in person from the same inventory on the phone, and send an SMS when the drop opens. Market it to makers, artists and apparel brands.

    Drops create urgent selling moments where an all-in-one phone setup beats juggling tools.

    Risks and how to handle them

    • Small segment

      Start with sellers already using drops.

    Evidence

    • Press releasesSquarespace press releases: "Permira Completes Acquisition of Squarespace" (October 2024); "Squarespace and Perplexity Partner to Reimagine Business Creation in the AI Era" (October 2025); a Super Bowl LX campaign with Emma Stone on "the Stakes of Domain Ownership" (February 2026); "Squarespace Balance" for business finances (March 2026); tools for "Selling in Limited Releases and Drops" (July 2026).Source
    • HiringSenior Director of Product, Mobile (posted September 17, 2026): mobile is evolving "from a companion to desktop into a primary growth channel"; "Sellers increasingly run their businesses from their phones, taking payments in person, sending invoices, and managing orders on the go"; measured on "seller activation, engagement, and revenue".Source
    • HiringSenior Product Director, Client Engagement Group (posted September 10, 2026): leads "the CRM, email campaigns, automations, and transactional communications"; "Our marketing tools are a critical lever in increasing product attach, reducing merchant churn"; owns "the Email Campaigns business line end-to-end", including SMS.Source

Wildcards 2

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

  • 20

    Squarespace's showcase is one of the few pages that declares its translations, but German and French prospects need local proof: sites by businesses like theirs, in their language.

    Medium impactLow effort First result in 1 quarter International Strategy and Ma…

    First action

    Ask 50 German and French customers for permission to feature them.

    How to measure it

    Gallery-assisted trials

    Now
    –
    Target
    1,000 a quarter
    By
    2 quarters

    Steps

    1. 1

      Find sites

      By industry and country.

      International Strategy and Marketing Lead 2 weeks

    2. 2

      Get permission

      From owners.

      International Strategy and Marketing Lead 2 weeks

    3. 3

      Interviews

      Short local stories.

      International Strategy and Marketing Lead 1 month

    4. 4

      Build galleries

      Locale pages.

      Web Engineering Lead 2 weeks

    5. 5

      Link

      From pricing and compare pages.

      SEO Lead 1 week

    6. 6

      Measure

      Assisted trials.

      Senior Manager International Strategy monthly

    First result
    1 quarter
    Cost
    Staff time
    Owner
    International Strategy and Marketing Lead

    Smallest test

    Publish ten German sites first.

    Why it works

    Curate 30 German and 30 French customer sites by industry, add short interviews, and link the galleries from the local pricing, template and comparison pages.

    Local examples answer the "does this work here?" question that translations alone cannot.

    Risks and how to handle them

    • Owners change sites

      Review the galleries each quarter.

    Evidence

    • Your websiteLanguage versions (checked October 21, 2026): Squarespace runs translated sites at de., fr., es., pt., it., ja. and ko.squarespace.com, and the homepage declares them with 24 hreflang links. But in a random sample of 80 English sitemap pages (excluding offer and press-coverage pages), 76 carry no hreflang at all, including /pricing, /templates, every /compare page and the blog; the German /preise and /compare/jimdo pages and the French /tarification page carry none either. Only a few pages, such as the homepage, /ecommerce, /scheduling and /showcase, declare their translations.Source
    • Your websiteHomepage: headline "A website makes it real"; "14M+ Entrepreneurs Served", "$36B+ Earned by Entrepreneurs", "200+" countries; "Start for free. No credit card required." The menu lists an AI Website Builder, Design Intelligence, Email and SMS Campaigns, SEO Tools, AI Visibility, Limited Releases, Financial Solutions, Domain Search and Business Email, plus Squarespace for Pros, the Circle partner program and Hire an Expert.Source
    • HiringInternational Strategy and Marketing Lead (Dublin, posted September 4, 2026): owns "marketing and go-to-market strategy execution across our European markets, from research and insights to agency partnerships, content, AEO strategy, and channel development", with "a current focus on Germany and France"; asked to "unlock new channels and partners"; German or French fluency preferred.Source
  • 21

    Core includes Google Workspace email free for the first year, and the Head of Domains & Email owns both lines. A new domain without email is a missed attach.

    Medium impactLow effort First result in 1 quarter Head of Domains & Email

    First action

    Measure today's email attach on new domains.

    How to measure it

    Email attach rate

    Now
    –
    Target
    +10 points
    By
    2 quarters

    Steps

    1. 1

      Baseline

      Attach by channel.

      Head of Domains & Email 1 week

    2. 2

      Design offer

      Preview and price.

      Head of Domains & Email 2 weeks

    3. 3

      Build

      Checkout step.

      Domains Engineering Lead 1 month

    4. 4

      Follow-up

      Seven-day email.

      Senior Product Director, Client Engagement Group 1 week

    5. 5

      Test

      Against current checkout.

      Head of Domains & Email 1 month

    6. 6

      Report

      Attach and retention.

      Senior Manager, Data Science and Machine Learning monthly

    First result
    1 quarter
    Cost
    Product time
    Owner
    Head of Domains & Email

    Smallest test

    Add the email preview to domain checkout for 10% of buyers.

    Why it works

    At domain checkout, offer a matching address (name@domain) with a one-click setup and show how it looks in an email preview. Follow up after seven days for those who skipped.

    A professional address makes the domain useful immediately and adds a second product that customers rarely cancel.

    Risks and how to handle them

    • Checkout friction

      Make it skippable.

    Evidence

    • Your websitePricing page: "Free for 14 days", "Pay annually to save up to 36%". Basic $25 a month or $19 billed annually, with a 2% online store transaction fee and 7% on digital content and memberships; Core $39 or $29 annually with 0% store fee and 5% on digital content; Plus $65 or $49; Advanced $139 or $99. Core includes Google Workspace email free for the first year.Source
    • HiringHead of Domains & Email (reports to the President): runs Domains and Email "as a business within a business" with the P&L; Squarespace calls itself "one of the world's largest domain providers"; the role owns "pricing, packaging, acquisition, retention, and expansion — including cross-sell and upsell into adjacent Squarespace products", and says "AI is fundamentally reshaping how people discover, register, manage, and derive value from domain names".Source
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See every playbook and website review

Independent research. Programmable wrote this playbook from public sources, as they stood on October 22, 2026, and cites them throughout. Squarespace did not commission, review or endorse it, and Programmable is not affiliated with Squarespace. 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 Squarespace runs its business.

Something wrong, or do you represent Squarespace? 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 306 ideas

    International pricing markup and hreflang, local comparison pages, homepage speed, the plan calculator, the offer-page cleanup and the name-tool handoff.

  2. Days 31 to 6012 ideas

    Domain-to-site and email attach, Email Campaigns triggers, the AI credits page, mobile activation, Acuity deposits, geo holdouts, the Forma launch brief, Circle partners, trial emails, AI visibility tracking and local galleries.

  3. Days 61 to 903 ideas

    Commit to the big bets: the entrepreneur index, domain registration inside AI assistants and the drop kit.

The research behind the plan

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

Customers

What customers say

Customers value polished templates and design. The most cited problem: transaction fees on the lowest plan.

  • Everything in one place: site, store, bookings, email and domain
  • Less flexibility than open platforms
  • In their words: “make it real”

Market

Competitive landscape

5 competitors compared: Wix, Framer, Hostinger, Jimdo and 1 more.

  • Gap to exploit: Correct local pricing in search and AI answers
  • Wix: Less consistent design quality
  • Framer: Narrower commerce and scheduling

Hiring signals

Squarespace is rebuilding how it goes to market.

  • International Strategy and Marketing Lead (Dublin): Germany and France, AEO and new channels. Ideas 1, 2, 14, 20.
  • Senior Manager International Strategy: AI-discovery playbook for owned markets. Ideas 1, 2, 16.
  • Director, GTM & Growth Marketing: Launch briefs, financial models and feedback loops. Ideas 5, 13.

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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