DocuSign vs Zapier

PolyAI, Taboola, Contentful, Docusign Win 2026 Digiday Tech Awards

The 2026 Digiday Technology Awards recognized companies leveraging AI and automation to enhance personalized experiences, targeting, and performance. PolyAI won Best AI Tool for its agentic dialog platform, which powers SafeRide Health's AI agent 'Steven', reducing speak-to-human rates from 55% to 2%. Taboola's Adam Singolda was named Technology Founder of the Year for launching DeeperDive, a conversational AI platform for publishers. Contentful and Docusign won Best Personalization & A/B Testing Platform, with Docusign using Contentful Personalization to launch tailored homepages across 20 audience segments, reaching 6.19 million monthly active profiles by March 2026. The awards span categories like affiliate marketing, agentic AI, CDPs, and clean rooms.

• PolyAI won Best AI Tool for its agentic dialog platform, with SafeRide Health's AI agent 'Steven' managing 80% of inbound calls.
• Adam Singolda, founder and CEO of Taboola, was named Technology Founder of the Year for DeeperDive.
• DeeperDive generates nearly three times more revenue per user for publishers.

Docusign Named a Leader in the IDC MarketScape for Worldwide Integrated Signing Workflow Software 2026

Docusign has been named a Leader in the IDC MarketScape for Worldwide Integrated Signing Workflow Software 2026, announced September 14, 2026.

Docusign Named a Leader in the IDC MarketScape for Worldwide Integrated Signing Workflow Software 2026

The Docusign IAM platform helps organizations extend the benefits of automation beyond signing to the full contract lifecycle, including AI-powered workflows, routing, review, and contract analysis.

Zapier CEO Grades PMs on AI Fluency Rubric

Zapier has released version 2 of its AI Fluency Rubric, which evaluates employees on mindset, strategy, building, and accountability. CEO Wade Foster explains the rubric's evolution and grading criteria in a podcast episode. The article details the history of AI fluency, from GPT-4's launch to internal memos at Microsoft, Meta, and Duolingo. It provides examples of 'Capable', 'Adoptive', and 'Transformative' ratings, emphasizing that the floor has moved and what was transformative in 2024 is now just adoptive in 2026. Foster also shares his personal 'robot staff' automations and stresses the importance of labeling AI-generated work and maintaining accountability.

• Zapier published version 2 of its AI Fluency Rubric on March 31, 2026.
• The rubric evaluates employees on mindset, strategy, building, and accountability.
• Wade Foster, CEO of Zapier, grades PM work products live on a podcast.

Zapier Automates Marketing Funnels with ChatGPT Work

Zapier's enterprise marketing team uses ChatGPT Work to automate funnel QA/QC, campaign asset creation, and reporting. The system performs quality assurance on thousands of leads monthly, surfaces recurring pipeline issues via an executive dashboard, and generates campaign assets quickly, allowing the team to focus on creative and strategic work. Zapier reports the automation yields seven-figure pipeline impact handed off to sales each month. The team plans to move toward always-on automation loops and a shared contextual “brain” integrating meetings, call recordings, and market insights.

• Zapier's enterprise marketing team uses ChatGPT Work to build automated funnel optimization systems.
• The system performs automatic QA/QC on thousands of leads every month.
• Zapier quantified the project's impact as seven figures in pipeline delivered to sales monthly.

Update Claude Code for Claude 5 Models

This newsletter explains how to adapt Claude Code workflows for Anthropic’s new 5-series models (Sonnet, Opus, Fable). The author highlights that the Claude team removed roughly 80% of the Claude Code system prompt for Opus 5 and found the model performed better, and recommends starting from Claude Code’s safe mode to identify obsolete customizations. The post links to an /update-to-cc-5 skill that automates the three recommended transformations, and lists related AI industry updates (Google Gemini leadership changes, Meta and Nvidia model releases, feature updates across tools, and recent fundraising). It also calls out several tooling updates (Zapier SDK, Wispr Flow, Superblocks, Arcads, Helena) and notes Sapiom’s $35M raise.

• Anthropic’s Claude Code team deleted ~80% of the Claude Code system prompt for Opus 5 and observed improved performance.
• Claude Code provides a safe mode to baseline behavior and compare outputs with customizations.
• The author published a downloadable skill that runs /update-to-cc-5 to automate recommended changes for Claude 5 compatibility.