Gabriel Dillon
GTM Lead, Personalization at Contentful
Oakland, California · Pacific time
I sell personalization software, which mostly means I spend the day talking about how personalization has let us down, why it's still definitely worth the squeeze, and why success must include user context, realtime signals, amazing content, and measurement of impact.
Most teams hear the word personalization and picture mail merge style {firstname}s scattered throughout some generic text. But it can be so much better: more obvious, easier to implement, and more useful. What do you offer a visitor on their third visit, or one who came in from a partner's site, or has been circling the same pricing page for a week? These are better questions than: how do we sync our data warehouse, can we model the audience accurately, or how do we publish a variant in the first place. Though those questions are pretty good, too...
I'm the GTM Lead for Personalization at Contentful, now part of Salesforce. I've worked here twice — once in partnerships, then again by way of an acquisition, and I've now been through one from both directions. Before that, I spent 4.5 years at Algolia, where for a while I was the only person selling in North America. Before that, ReadMe, which I co-founded and took through Y Combinator. Twelve years of selling technical products to people who are, quite reasonably, suspicious of salespeople.
I say I'm vaguely technical, or just a salesperson. Take your pick.
Current focus — as of September 2026
What happens to personalization when the content layer and the customer data layer stop being separate purchases.
I've been making that argument as a product point for a while. Now it's an org chart: Contentful has been acquired by Salesforce, so the two layers I've spent three years trying to introduce to each other sit inside the same company. Near term, it's business as usual for the accounts I work with. The questions get bigger, though. What does this look like at Salesforce scale, against Salesforce-shaped problems, for customers who already have the customer data and were never short of it?
The other half of my attention is on what AI does to all of our assumptions. Generating a thousand variants is now trivial. Knowing which of them deserved to exist is not, and that gap is where most of the disappointment lives. Personalized, agentic experience assembly is right around the corner.
Talks, podcasts & appearances
Supercharge personalized experiences with Contentful and AWS (AIM296)Lightning talk
A re:Invent session on running personalization natively on AWS with Contentful and Amazon Bedrock. Why context-aware personalization needs a scalable approach to content operations underneath it.
With Contentful
Why AI Content Stopped Working & What To Do About ItWebinar
Why AI-assisted copy drifts toward the generic, and four accountability questions worth asking about a piece of marketing content before it ships.
With John Graham
The New Rules of PersonalizationPodcast
A conversation with CGT editorial director Lisa Johnston about how consumer goods brands are redefining personalization through data, technology and experimentation.
With Lisa Johnston
Personalization in Retail: Creating Content-Driven Customer Experiences That ConvertWebinar
A fireside chat on data-driven personalization for retail marketers — tailoring content for peak shopping events, and what AI actually changes about the work.
With Irina Botea, Nicole Silberstein
Building Your Content Future with Contentful’s Gabriel DillonPodcast
On content infrastructure for consumer brands — recorded while leading partner GTM for Contentful’s personalization platform.
CMS Experts GroupMembership
An invitation-based forum of CMS analysts, practitioners and vendors convened by Janus Boye, meeting several times a year across Europe and North America.
With Janus Boye
Writing
Close the personalization gap: Activating Salesforce CRM data in real time with Contentful
How a Salesforce CRM connector lets teams segment on account type, plan tier and opportunity stage without writing custom code.
From static to responsive: Unlock dynamic content personalization
What it takes to move from content that sits still to content that responds — and where most teams stall on the way.
A comprehensive guide to MACH architecture
Microservices, API-first, cloud-native, headless — what MACH actually commits you to, and what it does not.
Headless CMS personalization: What you need to know
Why personalization built on a headless content model behaves differently from personalization bolted onto a rendered page.
Elsewhere