Gabriel Dillon

About

What I actually do

I'm the GTM Lead for Personalization at Contentful, now part of Salesforce. In practice that means I'm who an account team calls when a deal stops being about the CMS and starts being about data, experimentation, or why the personalization tool they bought two years ago is sitting unused.

That last one comes up more than the industry likes to admit. Personalization has a shelfware problem, and it's usually not the software's fault. Somebody bought a tool, nobody designed a program, and eighteen months later there are four experiences live and no one can say whether any of them did anything.

So I spend less time on features than you'd expect from someone carrying a number. Most of it goes to program design instead. What are you actually trying to move? Who's going to build the thing? And how will you know if it worked?

How I got here

I've been the first seller more than once. I co-founded ReadMe and took it through Y Combinator's W15 batch. I was the first sales hire in North America at Algolia, back when "search API" still needed explaining to most of the room. I ran partnerships at Contentful for a couple of years, left to join Ninetailed, and then helped turn a Contentful partnership into a Contentful acquisition — which is how I ended up back where I started, selling the thing I used to partner on.

The through-line is developer-adjacent products that are genuinely hard to explain. I like that problem. Turning an architecture diagram into a business case is the part of this job I'd probably do for free, though I'd rather you didn't mention that to my manager.

The thing I'll keep saying

Personalization and experimentation are two halves of the same coin. Most companies buy one, run it for a year, and wonder why it underdelivered. If you're changing what people see and you're not measuring whether the change did anything, you're not personalizing. You're guessing with extra steps.

The version of this that actually works is unglamorous. Fewer experiences, better instrumented. A real hypothesis. Someone whose job it is to look at the results on a Thursday.

Otherwise

Oakland, California. Pacific time, flexible. Most of what I know came from selling things I didn't fully understand yet and having to catch up in public, which I'd recommend to anyone who can stand it.

I take this work seriously. I try not to take myself too seriously about it, and I'm told I'm nice about the difference.

Career

  1. Aug 2025 — Present

    GTM Lead, Personalization

    Contentful — Composable content platform, acquired by Salesforce

    GTM strategy and direct sales execution for Contentful’s AI-native personalization product — discovery, solution design and deal support alongside account teams.

  2. Aug 2024 — Jul 2025

    Principal, Strategic Alliance Manager

    Contentful — Composable content platform, acquired by Salesforce

    Partner GTM for the personalization product post-acquisition, activating data, AI and testing capability across the MACH ecosystem with AWS, SAP, Twilio and Klaviyo.

  3. Dec 2022 — Aug 2024

    Head of Partnerships — GTM & Strategic Alliances

    Ninetailed — Personalization platform, acquired by Contentful

    Joined the senior leadership team owning the commercial and GTM motion. Built the alliance layer with Lytics, RudderStack and Contentstack, and sourced the Contentful partnership that became the acquisition.

  4. Oct 2020 — Dec 2022

    Strategic Partner Manager

    Contentful — Composable content platform, acquired by Salesforce

    Partner-sourced growth and co-sell across agencies, systems integrators and consultancies in North America and LATAM.

  5. May 2020 — Oct 2022

    Co-founder, Head of Partnerships and Sales

    Red Flag, Inc. — Contract and RFP risk analysis

    Early customer development for contract and RFP risk analysis, targeting large general contractors and law firms.

  6. Apr 2018 — May 2020

    Sr. Partner Sales Executive, Americas

    Algolia — Search and discovery API

    First global partner sales executive at Algolia. Built the ecosystem across systems integrators and commerce platforms including Shopify and Magento.

  7. Jan 2017 — Apr 2018

    Senior Account Executive, Mid-Market

    Algolia — Search and discovery API

    Mid-market new business across ecommerce, SaaS and retail; became the go-to resource for technical discovery and trained new hires in New York, Atlanta and London.

  8. Dec 2015 — Jan 2017

    Sales Representative — Founding GTM, North America

    Algolia — Search and discovery API

    First sales hire in North America. Opened the US market and evangelized API-first search before it was a category.

  9. Aug 2014 — Jul 2015

    Co-founder / Developer Evangelist

    ReadMe — Developer documentation platform (Y Combinator W15)

    Sales, support, developer relations, partner marketing — all of it mine. Closed Yammer, Box and Indiegogo in the first year, and the launch landed in Product Hunt’s top five.

  10. Jun 2013 — Apr 2014

    Marketing and Business Development

    moTwin — Mobile platform, US market entry

    US market entry for a French mobile platform company — positioning, messaging and early channel partnerships.

What I work on

  • Personalization
  • Experimentation and optimization
  • AI and AI Actions
  • Customer data activation
  • Value selling
  • Partnerships and alliances
  • MACH and composable architecture
  • Commerce and retail

Elsewhere

  • IndexTalks, podcasts and writing
  • TalksWhat I talk about, and a press kit

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