The 2026 Digiday Technology Awards winners put a clear marker down: AI and automation are no longer experimental side projects. The winning work shows operational AI agents, conversational publisher revenue tools, and no-code personalization moving into production — and producing results that can be measured in hours saved, revenue per user, and audience reach.
AI agents move from FAQ to front office
PolyAI and SafeRide Health took the Best AI Tool award for a deployment that is difficult to dismiss as a chatbot pilot. SafeRide Health deployed Steven, an AI agent built on PolyAI’s agentic dialog platform, to handle member authentication, ride bookings, cancellations and modifications without human handoffs.
The metric stack is notable. Steven now manages more than 80% of inbound calls, reduced speak-to-human rates from 55% to 2%, and saved 47,000 agent hours while speeding up patient service. For marketing and CX teams, this is a template for evaluating AI tools on business outcomes — deflection, resolution and operational hours — rather than engagement alone.
Conversational publishing keeps audiences and revenue on-site
Adam Singolda, founder and CEO of Taboola, was named Technology Founder of the Year. The recognition follows the 2025 launch of DeeperDive, a conversational AI experience built on a publisher’s own journalism. Instead of sending readers to external search or AI chat platforms, it uses reader behavior to deliver relevant answers while keeping audiences and revenue on publisher sites.
Adoption came through partnerships with Gannett and The Independent, while USA Today integrated reader questions into newsroom workflows. DeeperDive users generate nearly three times more revenue per user, with minimal cannibalization of existing revenue. The lesson: publisher monetization is shifting from pageviews alone to revenue per user and owned content utility.
No-code personalization scales beyond the developer queue
Contentful and Docusign won Best Personalization & A/B Testing Platform. Docusign used Contentful Personalization to replace its legacy CMS and launch tailored homepages for 20 audience segments without developer support, drawing on firmographic and intent data. By March 2026, the project reached 6.19 million monthly active profiles and tested more than 20 audiences across 7,000 pages in 14 languages.
The takeaway for marketing operations teams is practical: when personalization can be configured by content teams, experimentation and localization accelerate. The winning case connects three levers — audience data, modular content, and continuous testing — into a repeatable system.
Other winners worth tracking
- Best AI Platform: WRITER & Qualcomm
- Best Customer Data Platform: swsh x Rolling Stone
- Best E-Commerce Technology: The First Agentic Storefront by Swap
- Best Alternative Identification Technology: Seedtag and Qatar Tourism
- Best Data Management Platform: Optable & Unity
- Best Measurement Solution: Mastercard Media Measurement
- Best SEO Platform: Semrush One, an Adobe company
- Best Creator Marketing Platform: Influencity
What marketing teams should do next
Across all winners, Digiday highlights AI-ready infrastructure, first-party data, privacy and operational efficiency as defining priorities. For teams building a 2026 roadmap, the award cases point to three practical moves: test an AI agent in a high-volume service workflow, treat owned content and reader data as a retention asset, and reduce personalization bottlenecks by enabling non-developers to launch segmented experiences. The winners are not just a list — they are a benchmark for what production-ready martech and adtech looks like right now.
Source: Digiday
