beehiiv vs Squarespace

Product Roundup Week of November 2, 2026

In its Week 3 of 6 product update, beehiiv announced a series of new features and enhancements, including the launch of video capabilities in its community feature, allowing creators to upload videos up to 60 minutes long, either free or gated for paid members. The update also introduced an upgrade flow for every paid tier, enabling tailored welcome automations when subscribers move between tiers, and extended gift subscription scheduling to 45 days in advance. Additional improvements include click reports showing link text, poll results filtering out bots, faster subscriber exports, and new scheduling options for community posts and podcast episodes. The company also added merge tags in subject lines, draft links without signup walls, and AI-assisted scheduling via Claude or ChatGPT for higher-tier plans.

• beehiiv launched video in its community feature, allowing uploads up to 60 minutes, free or gated for paid members.
• New upgrade flow automation triggers for every paid tier, enabling tailored welcome sequences when subscribers move between tiers.
• Gift subscriptions can now be scheduled up to 45 days in advance (up from 30).

SiriusXM's Giggly Squad Deal Signals Shift to Creator Ecosystems

SiriusXM has signed a multi-year deal with creators Paige DeSorbo and Hannah Berner for their Giggly Squad podcast, reportedly valued at $160 million. The deal marks a strategic shift from traditional podcast networks to vertical creator ecosystems, encompassing audio, video, social, and live events. SiriusXM executives noted unprecedented demand, and the duo sold out multiple shows at Madison Square Garden. The article highlights broader industry trends: platforms like Spotify, Apple, and Amazon are competing for top creators, with Amazon's investment in New Heights cited as another example. Brands now seek to 'buy a creator' with exclusivity, while platforms like Substack and beehiiv are launching dynamic ad insertion and programmatic tools for creators. The podcast industry continues to pivot to video, with only 17% of Americans expecting audio-only podcasts, and new frontiers include short-form content and radio integration.

• SiriusXM signed a multi-year deal with Giggly Squad podcast creators Paige DeSorbo and Hannah Berner, reportedly valued at $160 million.
• Giggly Squad sold out four nights of a live podcast tour at Madison Square Garden, the first female-hosted podcast to headline the venue.
• SiriusXM is shifting from horizontal podcast networks to vertical creator ecosystems, supporting audio, video, social, and live events.

beehiiv Launches Podcast Advertising Tools

beehiiv has launched a suite of podcast advertising tools for creators and publishers of all sizes. The new capabilities include dynamic ad insertion, programmatic advertising, and creator-sold sponsorship management, all integrated into the existing platform. Creators can place and replace ads in old and new episodes without re-recording, and track impressions, revenue, and campaign performance. There is no minimum download requirement, and creators retain most of the programmatic revenue. The measurement is certified compliant with the IAB Tech Lab Podcast Measurement Technical Guidelines. beehiiv's CEO, Tyler Denk, stated that podcast advertising has traditionally been out of reach for smaller creators, and the goal is to democratize access. The company plans to introduce video hosting and distribution for podcasts and communities by the end of the year, with video monetization following in 2027.

• beehiiv launched podcast advertising tools with dynamic ad insertion, programmatic advertising, and sponsorship management.
• The tools are available on all beehiiv paid plans with no minimum download requirement.
• Creators retain most of the gross programmatic advertising revenue.

Squarespace lays off 19% of workforce in restructuring

In the AI-driven website building market, Squarespace and Webflow are adapting differently. Squarespace laid off approximately 19% of its workforce (around 300 employees) in November 2025, confirmed by a PR specialist. The restructuring aims to simplify operations and accelerate growth amid rising generative AI and 'vibe-coding' tools. Competitors like Wix have acquired AI builders, and Google launched similar features. Squarespace, which went public in 2021 and private in 2024 via a $7B deal, has introduced its own AI tools. Meanwhile, Webflow's CEO outlines strategic bets for SaaS survival, focusing on work AI can't do, targeting specific buyers, and using AI as a distribution channel. She cites market data showing AI-perceived companies trade at higher multiples, and notes Webflow's MCP server adoption success.

• Squarespace laid off ~19% of staff (about 300 employees) in November 2025 to streamline operations and prioritize growth.
• The layoffs are a response to the rise of generative AI and 'vibe-coding' tools in website building, with competitors like Wix and Google advancing AI.
• Webflow's CEO recommends focusing on work AI can't do, targeting a specific buyer segment, and leveraging AI as a distribution channel for SaaS survival.

Introducing SMS Campaigns: The Marketing Channel Your Customers Won’t Ignore

Squarespace announces the launch of SMS Campaigns, a new marketing channel integrated into its platform, allowing users to reach customers via text messaging.

August 2026 Product Updates

Squarespace published its August 2026 product updates announcement on August 25, 2026. The provided article text consists primarily of navigation and feature category listings such as AI Website Builder, Design Intelligence, Ecommerce, and Limited Releases. No specific product update details are available in the excerpt.

• On August 25, 2026, Squarespace published a press release titled 'August 2026 Product Updates'.
• The announcement is located at http://squarespace.com/blog/product-updates-august-2026.
• The text references features and categories including AI Website Builder, Design Intelligence, Ecommerce, Scheduling, and Limited Releases.