Gabriel Dillon

Founding Seller & YC Alum | Developer Oriented Sales and GTM Strategy | Built GTM at Algolia, ReadMe, Ninetailed & Contentful | AI & Agentic Tech

San Francisco5.9k followers

Contentful

ex-Algoliaex-Red Flag, Inc.

I've been the founding seller at two developer platforms — ReadMe (YC W15, co-founded) and Algolia (first AE in North America) — and I've spent the years since going deep on GTM strategy, product, and ecosystem to understand why technical buyers move.
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Now I want to bring that full picture back to a closing My background spans the whole stack of what makes developer-tool sales work: I've run discovery with eng leaders and CTOs, built the GTM motion from scratch, closed under pressure (83% of active pipeline in 60 days at a company in transition), and earned quota numbers in the 130–189% range. I understand what developers are building, what makes them trust a platform, and what gets a deal What I'm best at is the moment when a technical product needs to become a business decision. I translate architecture into outcomes, earn trust with skeptical buyers, and Developer products, martech built on data, AI/agent tooling, infra — this is where I work.

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GTM Index

CONTENTFULJOB
1. GTM Lead, Personalization
  1Y
2. Principal, Strategic Allia…
  11M
3. Strategic Partner Mgr
  2Y 2M
PARTNERSHIP LEADERSJOB
1. Member
  3Y 11M
NINETAILEDJOB
1. Head of Partnerships
  1Y 8M
RED FLAG,JOB
1. Co-founder, Head of Partne…
  2Y 5M
ALGOLIAJOB
1. Sr. Partner Sales Executiv…
  2Y 1M
2. Senior Account Executive,…
  1Y 3M
3. Sales Representative
  1Y 1M
README.IOJOB
1. Co-founder
  11M
SELECTED EARLY EXPERIENCESJOB
1. Various
  15Y 11M
MOTWINJOB
1. Mktg and BD
  10M

Job: Algolia — Senior Account Executive, Mid-Market Accounts · 2017-01 – 2018-04 — Led new business development across North America, targeting mid-market organizations (100–3,000 employees) in ecommerce, SaaS, and retail. Focused on consultative selling and solution fit for Algolia’s API-first search platform. Became the go-to resource for technical discovery, helping customers — and internal teams — understand how the platform integrated into modern architectures to drive conversion and user experience outcomes. Built trust with engineering and product leaders, not just traditional buyers. Trained and mentored new hires in New York, Atlanta, and London on pitch structure, product storytelling, and technical value articulation. This role marked the beginning of a tran…
Job: Red Flag, Inc. — Co-founder, Head of Partnerships and Sales · 2020-05 – 2022-10 — Managing early customer development and go-to-market program targeting top 50 general contractors and law firms to offer a solution to expedite contract/RFP risk management and analysis for multimillion-dollar cases.
Job: moTwin Inc. — Marketing and Business Development · 2013-06 – 2014-04 — Recruited by MoTwin, a French mobile platform company, to support its market entry strategy in the United States. Acted as a full-stack GTM lead across brand development, marketing communications, content, social, and early-stage channel partnerships. Played a key role in translating product positioning and messaging for U.S. buyers and partners — laying the groundwork for commercial expansion and demand generation in a new market.
Job: ReadMe.io — Co-founder / Developer Evangelist — GTM & Community Strategy · 2014-08 – 2015-07 — Co-founded ReadMe and took it through Y Combinator’s Winter 2015 batch, launching a documentation platform for developer communities that is now used by thousands of teams globally. Owned all commercial and external-facing functions from day one, closing initial deals with Yammer, Box, and Indiegogo, and driving developer adoption through joint launch campaigns with Mozilla, Product Hunt, and Watsi. The launch ranked among the top 5 most upvoted Product Hunt releases. Held responsibility for all external-facing functions, including sales, customer success, support, developer relations, and partner marketing. Positioned the platform as a category-defining solution for API-first and open-so…
Job: Algolia — Sr. Partner Sales Executive, Americas · 2018-04 – 2020-05 — Promoted from direct sales to become the first global Partner Sales Executive at Algolia, leading the expansion of its partner ecosystem across North America. Developed strategic alliances with systems integrators, technology vendors, and ecommerce platforms including Shopify and Magento. Evangelized the value of Algolia’s AI-powered, developer-centric Search-as-a-Service platform and translated it into actionable co-sell and integration partnerships. Supported field teams with partner enablement, solution fit, and GTM execution. Key wins included securing Algolia’s first white-label partnership and closing deals in collaboration with enterprise partners such as Capgemini, Microsoft, and…
Job: Selected Early Experiences — Various · 1999 – 2014 — Earlier roles spanned content, technical support, creative production, and early-stage business development — foundational experiences that shaped a cross-functional, product-adjacent GTM mindset. Product Strategy & Business Development, Border Stylo Assistant Media Editor, John Wiley & Sons, Inc. Senior Photo Retoucher, Getty Images Helpdesk Manager, Wesleyan University Client Engagement, Moving Brands Retail Lead, Barnes & Noble
Job: Algolia — Sales Representative — Founding GTM, North America · 2015-12 – 2017-01 — Hired as the first Sales representative in North America and tasked with building the company’s go-to-market motion from the ground up. Opened the U.S. market through outbound prospecting, discovery-led selling, and early-stage GTM experimentation. Targeted mid-market and enterprise accounts in SaaS and ecommerce, building the initial pipeline, securing flagship logos, and helping validate product-market fit across North America. Evangelized the value of API-first search before it became mainstream — playing a key role in shaping Algolia’s positioning for both technical and business stakeholders during its initial U.S. expansion.
Job: Contentful — GTM Lead, Personalization — GTM and Sales Execution · 2025-08 – present — Active in the sales motion across ~20 deals per quarter alongside AEs — running discovery, shaping solutions, and driving deals with eng leaders and platform teams across the addressable market. Responsible for both GTM strategy and direct sales execution for Contentful's AI-native personalization product. - Defining and executing GTM strategy for personalization - Driving adoption and revenue growth through lighthouse customers and partners - Collaborating with Sales, Product, and Partner teams to build repeatable motions - Building sales plays, enablement, and objection-handling frameworks for the field - Partnering with ecosystem integrators to extend reach and accelerate adoption
Job: Contentful — Principal, Strategic Alliance Manager — GTM Strategy (Ninetailed) · 2024-08 – 2025-07 — Directed the partner GTM strategy for Contentful’s personalization product (formerly Ninetailed), with an emphasis on activating data, AI, and testing capabilities across the MACH ecosystem. Collaborated cross-functionally with Sales, Alliances, and Enablement to equip partners — including AWS, SAP, Twilio, and Klaviyo — with the technical clarity and GTM strategy needed to sell the platform effectively. Translated complex architecture into sales-ready messaging, delivered high-impact partner training, and shaped co-sell narratives adopted across strategic accounts. Led workshops, webinars, podcasts, and live presentations to evangelize the platform. Supported the development of sales ena…
Job: Ninetailed — Head of Partnerships — GTM & Strategic Alliances · 2022-12 – 2024-08 — Joined Ninetailed's senior leadership team and owned both the commercial and GTM motion. Closed 83% of the active pipeline in under 60 days during a high-pressure business transition via a mix of direct sales execution, partner-sourced deals, and co-sell closes. Established and deepened alliances with Lytics, RudderStack, Contentstack, and other ecosystem partners to expand data-layer integration strategy and accelerate joint GTM motion. Represented Ninetailed at executive summits, the CMS Experts Group, and field-facing conferences — delivering partner-facing pitches and strategic product positioning. Sourced and secured the Contentful partnership, cultivating the relationship into a for…
Job: Contentful — Strategic Partner Manager — Co-Sell GTM & Ecosystem Growth · 2020-10 – 2022-12 — Directed partner-sourced growth and co-sell strategy across agencies, systems integrators, and digital consultancies, with regional focus on North America and LATAM. Ensured field teams had the right partners, narratives, and joint value propositions to win large-scale digital transformation deals. Delivered consistently high performance, achieving 131% of quota in Q3, 189% in Q4 (top global performer), and 149% in Q1, all immediately following paternity leave. Earned internal awards for GTM execution and partner management excellence. Built and sustained multi-year relationships with strategic partners that represented nearly half of new revenue during tenure. Worked directly with AEs an…
Job: Partnership Leaders — Member · 2022-09 – present
School: Y Combinator — Make something people want.
School: Georgetown University — MA, Communication, Culture and Technology
School: Wesleyan University — BA with High Honors, Psychology
School: Tradecraft — Sales Bootcamp Program
School: University of California, Berkeley - Extension
School: Zipfian Academy — Introduction to Data Science

Skills

Sales EngineeringTechnical SalesEnterprise Technology SalesStrategic AlliancesTechnology PartnershipsPartnership ManagementPersonalizationNew Business DevelopmentPartner DevelopmentSearchE-CommerceAutomationData PipelinesSolution SellingSalesCustomer Data Platform (CDP)Business StrategyArtificial Intelligence (AI)Software as a Service (SaaS)Content Management Systems (CMS)

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Gabriel Dillon

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