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How AI Content Recommendations work in AI Sidekick

Find the right content at the right time — without searching. This is the proactive half of AI Sidekick: instead of you asking a question, Spekit surfaces relevant Speks and Files directly inside the tools you already use.

"Searching requires knowing what to look for. Spekit AI Content Recommendations knows what you need."

 

1. What are AI Content Recommendations?

AI Content Recommendations (internally also called REX) uses AI and real-time context to proactively surface relevant content recommendations as you work — instead of relying on you to search manually, Spekit anticipates what you need based on the email you're writing or the call summary you're reading.

The result: faster meeting prep, more confident follow-up, and less time spent hunting for the right asset.


 

2. Where Recommendations work today

This feature is currently available on select pages within supported applications, and requires the Spekit Chrome Extension to be open to appear.

ApplicationSupported Context
GmailComposing or reviewing an email
Outlook (Browser)Composing or reviewing an email
SalesloftSales engagement workflows
Gong & ChorusCall recordings and summaries
Outreach KaiaCall insights and follow-up
Clari CopilotRevenue and deal conversations

Additional applications and workflows are planned for future releases.


3. What Recommendations support today

This first iteration focuses on the two moments reps hit most often:

Use CaseHow It Helps
Meeting PreparationSurfaces relevant knowledge before a call, so you walk in ready and confident
Post-Meeting Follow-UpRecommends content to review or share right after a call, to keep the deal moving

Content types recommended:

  • Speks — playbooks, battlecards, processes
  • Files — PDFs, PPTs, case studies, collateral

4. How Recommendations are generated

Recommendations are ranked by how closely they match the content on the page you're viewing — the stronger the match, the higher it sits in the Chrome Extension.

What affects the ranking:

  • Contextual relevance to the page
  • Keyword proximity and usage
  • Singular/plural word variations
  • Minor typos and spelling variations

What improves accuracy over time: the quality of recommendations depends directly on how much content you have and how well it's structured.

  • Rich content — upload case studies, battlecards, and product collateral so there's more for the AI to match against.
  • Metadata — use Custom Fields to add structured signals that help the AI match content more precisely.

5. How to enable and access Recommendations

Before you test it:

  1. Make sure you're on the latest version of the Chrome Extension.
  2. Confirm your team has Files populated — recommendations are noticeably stronger when there's real content to match against.

How to access it:

  1. Open a supported app (an email you're composing, or a call recording).
  2. Click the Spekit Dock to open the sidebar.
  3. Navigate to the "For You" section — this is where recommendations appear.7. Gmail & Outlook: do's and don'ts

Follow these to get accurate recommendations in email workflows:

✅ Do❌ Don't
Work with one email at a timeKeep multiple drafts open simultaneously
Expand long email threadsLeave important context collapsed
Keep the Spekit sidebar openExpect recommendations without the sidebar active

Related articles: "Using AI Sidekick Chat" for the ask-a-question half of Sidekick, and "Getting Started: Install and Set Up the Spekit Chrome Extension" if Recommendations aren't appearing and you need to confirm your extension setup.

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