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Overview of Spekit AI Sidekick

  • Updated

Your just-in-time enablement coach. Unifying real-time answers, tailored content, and coaching directly within your workflow.

 

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1. What is Spekit AI Sidekick?

Spekit AI Sidekick is an AI-powered, just-in-time enablement assistant that helps reps get answers, find content, and move deals forward—without leaving their workflow. It brings answers, content, and coaching together in one place, delivering support directly inside the tools reps already use, like CRM, email, and other sales platforms.

Beyond answering questions, Sidekick also powers Deal Rooms, dynamic Playlists, and AI-driven content experiences—making it the central hub for enablement across your organization.

 

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2. What can AI Sidekick help you do?

AI Sidekick is designed around real rep workflows, helping teams act faster and more confidently in critical moments.

Get Answers Instantly

Receive clear, accurate answers to sales, product, and process questions—without searching or waiting on teammates.

Find and Share the Right Content

Sidekick recommends the most relevant decks, guides, playbooks, and messaging based on deal and account context, so reps always share the right content at the right time.

Prep for and Follow Up on Deals

Use Sidekick before calls to review product updates or competitive context, and after calls to draft follow-ups or find next-step resources.

Stay Aligned with Process and Best Practices

Surface admin-pinned guidance, opportunity-specific tips, and required field documentation to keep deals moving and data clean.

 

3. Where can you access AI Sidekick?

You can open Spekit AI Sidekick in several ways, depending on how you work:

Access Method Where It Lives How It Works

Spekit Sidekick 

(Chrome Extension)

 Any webpage  AI Sidekick opens by default when you launch the extension, giving you instant, in-context answers and recommendations.
Spekit Web App Spekit Web App Open Sidekick by clicking the AI Ask icon to ask questions and explore content.
Spekit Search Bar Spekit Web App and Sidekick Type a question into the search bar and choose Ask using Spekit AI Sidekick to route it to Sidekick.
Keyboard Shortcut Anywhere in your browser

Open or close Sidekick instantly without interrupting your workflow.

Windows: Ctrl + Shift + K 

Mac: Cmd + Shift + K

 

 

4. What will you see in AI Sidekick?

When AI Sidekick is open in the Chrome Extension, you may see different sections depending on your tools and permissions.

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Feature Availability  What it Surfaces
1. Deal Rooms Customers with Deal Rooms enabled View the Deal Room tied to the account, preview/edit/share content, and track deal-related materials as the opportunity progresses.
2. Content to Share Externally Customers with Trackable Links enabled Recommended buyer-facing content based on deal or account context; share guides, decks, and resources quickly.
3. Internal Knowledge All users Context-aware recommendations based on the page or tool you’re using; find internal resources and best practices fast.
4. Pinned Topics All users Admin-pinned content relevant to the current platform or page, for fast access to high-priority information.
5. Pinned Guidance for Opportunities  Salesforce only Opportunity-specific guidance pinned by admins, including process reminders, best practices, and field definitions.
6. Document these Opportunity Fields Salesforce only Highlights empty or undocumented Opportunity fields to ensure Salesforce data stays complete and accurate.

 

 

5. Search smarter with AI Sidekick slash commands

Slash commands give you direct control over where Sidekick searches—without leaving your workflow.

/search [keywords]
Searches internal Spekit content for fast, keyword-based results.
Example: /search proposal deck

/google [query]
Searches the web using Google and blends those results with Spekit knowledge for more informed responses.
Example: /google competitor funding

 

Slash commands help you combine trusted internal knowledge with real-time external context for faster, more relevant outputs.

 

6. What to expect from AI Sidekick

Why Is AI Sidekick in Beta?

AI Sidekick is currently in beta as we continue to learn from real-world usage and refine the experience. This allows us to improve accuracy, relevance, and performance before broader feature expansion.

Can I save or favorite conversation history in Spekit AI Sidekick?

At this time, Spekit AI Sidekick does not save your conversation history once the chat window is closed. However, as long as the tab and chat window remain open, the conversation will persist.

💡 Pro Tip: To save information, open the sources provided by Sidekick and Favorite (Star) them in your sidebar for permanent access! 💡 

How do I refresh Spekit AI Sidekick features if they aren’t appearing?

If features aren’t appearing as expected:

  1. Refresh your browser page.
  2. Close and reopen the Spekit sidebar.
  3. Confirm your Chrome Extension is updated to version 2025.02.26 or later.

Is Spekit AI Sidekick restricted to providing responses based on user access?

Yes, Spekit AI Sidekick only generates responses based on the content the user has permission to access. This ensures that sensitive or restricted content remains secure and unavailable to unauthorized users.

Does Spekit AI Sidekick retain context between questions?

Currently, Spekit AI Sidekick operates on a "one question → one answer" basis. It does not retain conversational context or history between questions and answers. 

What data does a “recommended question” in Spekit AI Sidekick use?

Recommended questions are generated using:

  • Your original question
  • The answer summary
  • Titles of the sources used

This keeps suggestions relevant to your immediate task.

 

7. Tips for getting the most out of AI Sidekick

Spekit AI Sidekick is more than just an AI assistant—it’s a contextual, just-in-time enablement partner. Use these best practices to unlock its full potential:

1. Ask for Specific Content

  • Request the exact resource you need, like case studies, one-pagers, objection-handling guides, or competitive battlecards.

  • Example: “Show me a case study for the healthcare industry.”

  • Example: “Do we have a one-pager for our new product feature?”

2. Get Sales Cycle and Process Support

  • Ask about your company’s sales stages, qualification frameworks, or steps for handling common objections.
  • Example: “What are the key stages in our sales process?”
  • Example: “What questions should I ask during a discovery call?”

3. Keep Questions Company-Specific

  • Sidekick uses your organization’s knowledge, not the public web. Focus questions on company processes, content, or terminology.
  • Example: “What’s our process for submitting a pricing exception?”
  • Example: “Where can I find our latest messaging for [product]?”

4. Use Sidekick to Prep and Follow Up

  • Before a call: “What’s the latest product update I should mention to this customer?”
  • After a call: “What's the latest follow-up email template?”

5. Organize and Share Helpful Content

  • Favorite resources or add them to a Playlist. Share useful answers with teammates to spread best practices.

6. Stay in the Flow—No More Tab Overload

  • Use Sidekick directly in your workflow tools (Salesforce, Chrome, etc.) to avoid switching between tabs.

7. Understand When Recommendations Appear

  • Sidekick recommends content based on the context of what you’re working on (Gmail, Outlook, Salesloft, Gong, Chorus, Outreach Kaia, Clari Copilot), not during live calls.

8. Focus on Productive, Actionable Questions

  • Sidekick gives clear, actionable answers. For broad/off-topic questions, it may prompt you to focus on productive questions.

💡 Pro Tip: Instead of “Tell me everything about marketing,” try, “What are the key digital marketing strategies our company uses for lead generation?”💡

9. Refine, Experiment, and Give Feedback

  • If an answer isn’t quite right, rephrase or add detail. Share feedback with your enablement team to keep Sidekick’s knowledge up to date.

Sidekick is most effective when your questions are focused on your company’s resources and needs. Use these tips to unlock faster answers, better coaching, and more consistent content—right where you work.

 

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