Side-by-side comparison · Productivity & Notes
Box AI vs Shortwave vs Wispr Flow
Everything that matters when choosing between them, in one place: our rating, what each can do, what they cost, and the trade-offs.
Comparing 3 tools, the maximum.
At a glance
Pick it if: Companies that already keep their contracts and documents in Box and want AI to work on them securely.
Pick it if: Busy Gmail and Google Workspace users who want AI to search, sort and draft their email.
Pick it if: Anyone who writes a lot during the day and is tired of typing it, including people who brief AI tools constantly.
Wispr Flow scores highest overall, but Shortwave gives you more for your money. Which one is right comes down to what you value most.
Overview
| Attribute | Box AI | Shortwave | Wispr Flow |
|---|---|---|---|
| In one line | Ask questions of, summarise and pull data from your company's Box files. | AI email app for Gmail that searches, sorts, drafts and acts on your inbox for you. | Talk instead of type, anywhere on your computer or phone, and get clean text back. |
| Pricing model | Paid | Freemium | Freemium |
| Starting price | From $5/user/mo | $18/mo | $15/mo |
| Free plan | No | Yes | Yes |
| Works with Claude Code | Yes | No | No |
Rating breakdown
Our scores out of 5. The higher bar in each row is highlighted.
| Attribute | Box AI | Shortwave | Wispr Flow |
|---|---|---|---|
| Overall rating | 3.8 | 4.2 | 4.4Winner |
| Ease of useHow quickly someone non-technical gets value from it. | 4.0 | 4.0 | 5.0 |
| FeaturesHow completely it covers its own job, and how well the pieces fit together. | 4.0 | 4.5 | 4.5 |
| Output qualityHow good the results are before you fix them. | 4.0 | 4.5 | 4.5 |
| Value for moneyWhat you get for the price, including the free plan. | 3.0 | 4.0 | 3.5 |
| Speed & reliabilityHow fast it is and how often it falls over. | 4.0 | 4.0 | 4.5 |
Feature comparison
A tick means it does this today. A dash means we haven't checked.
| Attribute | Box AI | Shortwave | Wispr Flow |
|---|---|---|---|
| Access & platform | |||
| Free plan | No | Yes | Yes |
| Mobile app | Yes | Yes | Yes |
| Desktop app | Yes | Yes | Yes |
| Browser extension | – | – | No |
| API access | Yes | – | No |
| Teams & business | |||
| Team workspace | Yes | Yes | Yes |
| Enterprise plan or SSO | Yes | – | Yes |
| Connects to other apps | Yes | Yes | – |
| Open source or self-hosted | No | No | No |
| AI abilities | |||
| Works with your files | Yes | Yes | No |
| Understands images | Yes | – | No |
| Makes images | No | No | No |
| Makes video | No | No | No |
| Writes code | – | – | No |
| Runs agents or automations | Yes | Yes | No |
| Learns your brand or style | – | Yes | Yes |
| Works in many languages | Yes | Yes | Yes |
| Capabilities score | 10/ 17 | 9/ 17 | 7/ 17 |
Pricing
Plans as listed on each vendor's site when we last checked. Confirm before you buy.
| Attribute | Box AI | Shortwave | Wispr Flow |
|---|---|---|---|
| Plans | Business Starter From $5/user/mo billed yearly Small teams that just need file storage. | Free Free Trying it on your Gmail inbox. | Free Free Light users and trying it out. |
Business See website Teams wanting AI on one file at a time. | ProOur pick $18/mo Individuals who use the AI daily. | ProOur pick $15/mo, or $12/mo billed yearly Anyone who talks more than they type. | |
Enterprise See website Companies with compliance needs and light AI use. | Business $30/seat/mo Teams who share threads and need more AI. | Growth $23/user/mo, or $18/user/mo billed yearly Teams with security or compliance needs. | |
Enterprise PlusOur pick Custom, billed yearly Teams that want AI across many files. | Premier $45/seat/mo Heavy users with complex email workflows. | Enterprise Custom Large managed rollouts. | |
Enterprise Advanced Custom Large companies building custom AI agents. | Max $120/seat/mo People who live in email all day. | ||
| Which plan to pick | If you want Box AI to be genuinely useful, Enterprise Plus is where multi-file questions and Box Agent start. On Business you only get single-file questions and must buy AI units. Ask sales to estimate your AI unit use before signing. | Start on Free for a week to see if you like the app. Pro is enough for most individuals; pick Business only if you share threads with a team. Every paid plan has a 14-day free trial. | Free tells you within a day whether talking suits you. If you hit the weekly cap, which most people do fast, Pro on the yearly plan is the one. Growth is only about security paperwork. |
Key features
| Attribute | Box AI | Shortwave | Wispr Flow |
|---|---|---|---|
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Pros and cons
| Attribute | Box AI | Shortwave | Wispr Flow |
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Who each one is for
| Attribute | Box AI | Shortwave | Wispr Flow |
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Questions people ask
Which is better, Box AI, Shortwave or Wispr Flow?
Wispr Flow scores highest overall in our ratings (Box AI 3.8/5, Shortwave 4.2/5 and Wispr Flow 4.4/5). Box AI is best for questions and summaries on long contracts and pulling key fields out of contracts and invoices. Shortwave is best for finding old emails by describing them and clearing a cluttered Gmail inbox quickly. Wispr Flow is best for dictating emails and messages and long prompts for AI tools.
Which is cheaper, Box AI, Shortwave or Wispr Flow?
Box AI: There's no free plan. Paid plans start at From $5/user/mo. Shortwave: There's a free plan, and paid plans start at $18/mo. Wispr Flow: There's a free plan, and paid plans start at $15/mo.
Which is easier to use, Box AI, Shortwave or Wispr Flow?
Wispr Flow rates highest for ease of use in our scores. Anyone who writes a lot during the day and is tired of typing it, including people who brief AI tools constantly.
How we compare
Ratings are our own, from using each tool, across ease of use, features, output quality, value for money, speed & reliability.
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