CloudFest 2026 Goes Business: Why WordPress Agencies Should Pay Attention

In this episode of Within WordPress, we sit down with Carole (CloudFest) and Mark Weisbord (CEO of Greyd) to explain what is changing at CloudFest this year, and why it matters for agencies and WordPress businesses.

The headline is the launch of the WordPress Business and Agency Summit on the Monday before the main CloudFest event. We position it as a connector between the CloudFest Hackathon and the main CloudFest conference, and as a deliberate step toward giving agencies and WordPress businesses a more relevant, more pragmatic, more commercially useful program than the traditional “WordPress Day” format.

We unpack the difference between WordCamps and CloudFest. WordCamps remain community-first, volunteer-driven, and primarily focused on education and connection inside the WordPress community. CloudFest is a for-profit, cloud and hosting industry conference with a very different scale, structure, and mission, and it can build a dedicated business-focused layer around WordPress without trying to turn WordCamps into something they were never designed to be.

This year’s Summit expands the former WP Day into a full-day, two-track program, adds an exhibition area, and targets roughly 800 attendees in a more intimate setting inside a much larger 10,000+ person event. From Mark’s perspective, if we want growth and new partnerships, we need to attract agencies outside the WordPress community, and we need content that connects to direct business impact. That means talks about sales, pricing, go-to-market, agency operations, maintenance revenue, and what it really takes to move from agency work into becoming a product company.

We also talk about the CloudFest Hackathon as a uniquely valuable environment for multi-day collaboration and deeper conversations that rarely happen at faster-paced conferences. Carole connects that to a broader goal: cross-CMS collaboration and strengthening the open web, so we do not end up with a future where a handful of platforms dictate where and how people can publish.

We close with practical attendance advice, a reality check that the Hackathon is already fully booked, and the key dates for the Summit and the main CloudFest event.

00:00 – Cold open: editing workflow and “wave” marker for cuts
00:01 – Welcome and setup: two guests, and why this episode is different
00:02 – Carole: WordPress community background and CloudFest involvement
00:03 – What CloudFest is: scale, audience, and Europa-Park as the venue
00:04 – “Everything is different this year”: why we are doing this episode
00:05 – The new WordPress Business and Agency Summit: where it fits in the week
00:06 – Mark Weisbord (Greyd): the missing business layer in WordPress events
00:07 – From “WP Day” to a bigger Summit: what changes operationally
00:08 – Two tracks, full day, and a dedicated exhibition area
00:09 – Why this format matters: connecting agencies, partners, and real-world solutions
00:11 – WordCamps vs CloudFest: why they serve different purposes
00:12 – Sponsor reality: ROI pressure, leads, and reaching agencies outside the bubble
00:13 – Content shift: business impact over general tech presentations
00:14 – WordCamps still matter, but they are not the vehicle for everything
00:16 – Biggest change: bring in agencies outside WordPress, plus an entertainment factor
00:18 – CloudFest vibe: opening party, Lords of the Uptime, and the venue experience
00:23 – Practical advice: stay multiple nights for Summit welcome + opening party
00:25 – Hackathon value: multi-day conversations and real collaboration time
00:28 – Hackathon evolution: cross-CMS collaboration and protecting the open web
00:33 – Why agencies benefit: broader ecosystem exposure than a WordCamp context
00:36 – What the Summit covers: sales, pricing, playbooks, productizing, maintenance
00:40 – How Summit pillars extend into t...

Chapters

• (00:00:00) - Within WordPress: A Special Episode
• (00:01:22) - A Word about Cloud Fest
• (00:04:25) - Building the Business Side of WordCamp
• (00:10:08) - Cloudfest: The Business of WordCamp
• (00:17:22) - Entertainment at Cloud Fest 2018
• (00:24:22) - Bill Gates at the Hackathon
• (00:34:38) - Wonders of the Web: Business and Topics
• (00:38:10) - Cloudfest 2020: A day for agencies?
• (00:41:10) - Wonders of the Web: Education and Business
• (00:44:31) - WordCamp Europe: A 10,000-Person Event
• (00:47:33) - Cloud Fest 2018: The Hackathon
• (00:50:29) - Cloudflare