How much does Ruby cost? Is there a free plan?

Ruby operates on a freemium model. You can start for free, but you need your own Claude subscription to power the live suggestions. The free tier likely has usage limits, while paid plans unlock more features like custom skills and extended usage. Exact pricing details are not publicly disclosed, so check the official website for current plans.

Can I try Ruby without a Claude subscription?

No, Ruby requires you to bring your own Claude subscription. The tool uses your Claude API key to generate real-time suggestions. Without a Claude subscription, Ruby cannot function. This is a core requirement, not an optional add-on.

What are the best alternatives to Ruby for live call coaching?

Alternatives include tools like Gong, Wingman, and Fathom, but most focus on post-call analytics rather than live suggestions. Ruby is unique for real-time prompting during calls. If you need live assistance without a Claude subscription, consider Clari or Chorus, but they lack the same in-the-moment coaching feature.

Who is Ruby best for?

Ruby is ideal for founders on discovery calls who need to ask sharper questions, product managers during user interviews, sales AEs in high-stakes demos, and recruiters interviewing candidates. If you have a critical conversation where one question can change the outcome, Ruby helps you ask it at the right moment.

Who should avoid using Ruby?

Avoid Ruby if you don't have a Claude subscription, need shared analytics or coaching dashboards for a team, only want post-call transcription, or use Windows or Linux. Ruby is macOS-only (14.4+, Apple Silicon or Intel) and focuses on live help, not recording.

What are the key limitations of Ruby?

Key limitations: requires macOS 14.4+ (no Windows/Linux), requires your own Claude subscription, no team-level analytics or coaching dashboards, and no bot-free recording (transcription is local). Also, it's designed for live assistance, not post-call summaries only.

What integrations does Ruby support?

Ruby does not list specific third-party integrations. It works as a standalone macOS app that uses your Claude subscription. It likely supports any tool you can run on macOS, but there are no built-in integrations with CRM, calendars, or video conferencing platforms mentioned.

Is Ruby easy to set up? What is the learning curve?

Setup is straightforward: sign in with your Claude subscription, brief Ruby on your goal and skill, then take calls. The learning curve is low for users familiar with Claude and basic apps. However, configuring custom skills may require some upfront effort to get the most out of it.

Is Ruby good for sales calls?

Yes, Ruby is specifically designed for high-stakes sales demos and calls. It provides real-time question suggestions to help you close deals. Sales AEs can use custom skills like 'sales' to get prompts that uncover buyer needs. However, it relies on your own Claude subscription, so you need that first.

Does Ruby record calls or join as a bot?

No, Ruby does not join calls as a bot and does not record audio. It listens via local transcription from your microphone and provides suggestions without being visible to others. Your transcript and data remain private and yours.

Can Ruby be used for user interviews?

Absolutely. Ruby is great for product managers conducting user interviews. You can set a goal and use skills like 'the-mom-test' to ask deeper questions. The live suggestions help you probe without breaking flow, and post-call recaps save you from note-taking.

What macOS versions does Ruby support?

Ruby supports macOS 14.4 and later, including both Apple Silicon and Intel Macs. It does not support Windows or Linux, so you need a compatible Mac to use it.

Ruby

Freemium

Live AI call assistant that slides you the right question at the right moment.

By Tanmay Verma, Founder · Last verified 02 Jul 2026

0 views

Added 7d ago

95/100Safe Bet

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In short

Ruby — Live AI call assistant that slides you the right question at the right moment. Best for Founders on discovery calls needing to ask sharper questions in real time, Product managers gathering requirements during user interviews, Sales AEs in high-stakes demos where one question can close. Free to use.

Compared withvs Hi Marley vs Chatlyn vs B Rokratt

Is Ruby actually worth it?

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Editorial Verdict

Best for

Founders on discovery calls needing to ask sharper questions in real timeProduct managers gathering requirements during user interviewsSales AEs in high-stakes demos where one question can closeRecruiters interviewing candidates and wanting to probe deeper

Not ideal for

Anyone without a Claude Code subscriptionTeams needing shared analytics or coaching dashboardsUsers who only need post-call transcription (not live help)Non-macOS users (Windows/Linux not supported)

Ruby fills a real gap — live prompting during calls — but its dependency on Claude Code and macOS-only availability narrows its audience. If you're a solo operator who already uses Claude and takes high-stakes calls, it's worth a try. Otherwise, wait for broader platform support or a bundled pricing model.

Compare with: Ruby vs Chorus, Ruby vs Fellow, Ruby vs Demodesk

Last verified: July 2026

Viability Score

95/100

Safe Bet

How likely is Ruby to still be operational in 12 months? Based on 4 signals — momentum (how recently it shipped), wrapper dependency, revenue model, and web presence.

momentum

100

funding runway

website health

wrapper dependency

100

Last calculated: July 2026

How we score →

Key Features

Live real-time suggestion pill during calls
Pre-call briefing with custom goals and skills
Post-call automated recap generation
Hidden from screen share
Uses user's own Claude subscription
Local transcription feeds Claude for context
Support for custom skills (e.g., the-mom-test, sales, hiring)
macOS 14.4+ support (Apple Silicon and Intel)

About Ruby

FreemiumIntermediateNo APIDesktop

Ruby is an AI-powered live call assistant that helps you ask better questions during important conversations. Unlike traditional notetakers that only provide summaries after the fact, Ruby listens in real time and discreetly suggests the question worth asking through a small pill visible only to you. It is designed for sales calls, hiring interviews, founder conversations, and any high-stakes meeting where asking the right thing in the moment can change the outcome. How it works: you sign in with your own Claude subscription, brief Ruby on your goal and a 'skill' (e.g., 'the-mom-test', sales, hiring, or custom), then take the call. Ruby transcribes the conversation locally and feeds it to Claude, which chimes in with timely suggestions. After the call, Ruby generates a recap so you don't have to write notes. What makes Ruby different is its focus on live assistance rather than post-call summaries. It runs on your own Claude subscription, so there is no extra AI bill. The tool is private by default: no bot joins the call, nothing is visible on screen share, and your transcript and notes remain yours. It's a subtle, in-the-moment coach rather than a background recorder. Ruby is currently available as a macOS desktop app (14.4+ required, Apple Silicon and Intel). It requires Claude Code (the terminal CLI), not the Claude desktop app. It's best suited for individuals who have a Claude subscription and need real-time prompting during calls, not for teams or enterprise rollouts.

Behind the Verdict

Ruby is a smart, niche tool that solves a problem most AI assistants ignore: helping you in real time, not after the fact. If you've ever hung up a sales call thinking 'I should have asked that,' Ruby is designed for you. It works well because it's unobtrusive — a small pill, hidden from screen share, that suggests questions mid-conversation. The pre-call briefing (goal + skill) lets you tailor it per meeting. And since it uses your own Claude subscription, there's no extra AI bill. But the caveats are real. Ruby requires Claude Code (the CLI), not the desktop app. That's a less common subscription. macOS 14.4+ only, so Windows and Linux users are out. No team features, no analytics dashboards, no integrations beyond Claude. Comparatively, tools like Otter.ai or Fathom focus on post-call transcripts, while Ruby is unique for live assistance. But those tools work cross-platform and don't require an external AI subscription. In practice, Ruby is best for founders on discovery calls, PMs gathering requirements, or recruiters interviewing candidates — one-on-one conversations where a timely question can change the outcome. It's not for team use or anyone who just wants a notetaker. Where it bites: if you don't already have Claude Code, you must buy it separately. And if you're used to a notetaker that joins the call and auto-saves, Ruby's live-only approach may feel different. Bottom line: Ruby is a clever tool for a specific persona. If that's you, try the free version first.

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Use Cases

Ask the one sharp question that closes a deal during a live sales demo
Never forget to probe deeper during a customer discovery call
Get real-time coaching on hiring interviews without a second person
Receive a structured recap immediately after the call ends
Prepare for calls with a brief that customizes Ruby's suggestions

Models Under the Hood

Claude Sonnet 4.6

Limitations

Ruby requires a separate Claude subscription (the terminal CLI, not the desktop app) and works only on macOS 14.4+.
It does not join the call as a bot, so suggestions rely entirely on local transcription quality.
There is no web or mobile version, and no team features for shared learning or analytics.

12-month cost

Project the real annual outlay, including the implied monthly cost when only an annual tier is published.

Plan

Annual total

Free

Over 12 months

Effective monthly

Free

Billed monthly

Vendor list price only. Add-on usage, seat overages, and contract minimums are surfaced under Hidden costs & gotchas.

Integrations

Claude (Code CLI)

Resources & Guides

Resourceruby.codeongrass.com
Home · Ruby
Helpful link from ruby.codeongrass.com

Frequently Asked Questions

Tools that pair well with Ruby

Common stack mates teams adopt alongside Ruby, with the specific reason each pairing earns its keep.

Chorus

Conversation intelligence for revenue teams — record, transcribe, and analyze sales calls.

Fellow

Enterprise-secure AI meeting assistant for transcription, notes, and summaries

Demodesk

AI sales agents that record, transcribe, analyze, and automate CRM updates

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