Overview of Spekit AI Sidekick

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

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 within the tools reps already use, such as CRM, email, and other sales platforms.

Spekit AI Sidekick consists of two main features:

Ask AI Sidekick (Formerly Sidekick Chat or AI Assist)

Ask AI Sidekick is an intelligent, in-the-flow enablement assistant designed to provide instant, accurate answers and guidance directly within the applications you use daily. It functions like a research librarian for your company's internal knowledge.

• Instant Answers: Ask questions directly in the chat sidebar, and the AI will synthesize a concise, accurate response based exclusively on your company's vetted internal content (Speks and files).
• Grounded in Trust: It uses an adaptive Retrieval-Augmented Generation (RAG) pipeline to ensure answers are derived only from your internal materials, preventing the use of unverified external data.
• Permission-Aware: The system strictly respects your existing user permissions; it will never surface a document or answer that you are not authorized to view.
• Actionable & Cited: Every response is designed to be direct and includes source citations, allowing you to verify the information and explore the original source materials further.

By meeting you where you work, Ask AI Sidekick eliminates the need to context-switch between different tools to find the information you need to sell or perform your job effectively.

AI Content Recommendations (REX)

AI Content Recommendations, also known as REX, is a proactive feature within Spekit AI Sidekick designed to surface relevant content, training, and resources to your team exactly when they need them, without requiring them to search.

How It Works

• Proactive Discovery: REX analyzes context signals from your daily workflow—such as the email you are drafting, the Salesforce opportunity you are viewing, or the call summary you are reading—to identify the most relevant enablement materials.
• Unconscious Discovery: Because it is dynamic and tailored to each user's unique needs, it surfaces content that reps might not even know exists, helping them prepare for meetings or follow up on deals more effectively.
• Workflow Integration: It works seamlessly across your revenue toolchain, including Gmail, Outlook, Salesforce, Gong, Chorus, Salesloft, and Outreach Kaia, appearing directly in the Spekit sidebar.

Key Benefits

• Less Context-Switching: Reps no longer need to leave their current application to hunt for battlecards, case studies, or playbooks.
• Increased Content Adoption: By surfacing buried or underutilized content in real-time, REX gives your enablement materials a second life.

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:

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, permissions, and the page you're currently on.

Related article: Want content to find you automatically? AI Content Recommendations proactively surfaces relevant Speks and Files based on the context of your current task or conversation—so the information you need comes to you, without searching.

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. 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.

7. AI Sidekick FAQs

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.