6,622 tools, each one opened, scored and signed by a Toolio reviewer

Winn.AI

Real-time AI guidance during sales calls, but limited to up to 25 fields.

Checked 3 Oct 2026 Reviewed by Alex Listed since September 2024

Screenshot of Winn.AI

At a glance

Starts at $19 per seat monthly, starting at Includes up to 25 fields of custom CRM updates.
Free tier No
Platforms Web, macOS, Windows
Best for Sales teams needing real-time call coaching.
Not for Sales teams with complex customization needs

3.9 out of 5

Scored by Alex after real use

Our verdict

WINN.AI provides live AI support for sales reps. It's great for those looking to enhance their call performance through automated insights and real-time assistance. However, it may not be the best choice if you need more than 25 fields in your CRM updates or advanced customization options.

✓What it does well

Real-time guidanceProvides live coaching during calls, improving call quality.
Automated CRM updatesUpdates CRM automatically with key information from calls.
Playbook learningAdapts to changing playbooks and individual rep needs.

✕Where it falls short

Limited field countOnly supports up to 25 fields in CRM updates, limited flexibility.
High entry cost for enterprise planEnterprise plan starts at $39 per seat monthly with many advanced features.
Customization limitationsDoesn't offer unlimited customization options or extensive AI insights out of the box.

Key features

Automated follow-upsSends smart call summaries and follow-up emails after calls.
Customizable talking pointsIncludes over 35 customizable AI-powered talking points for calls.
AI meeting prepGenerates next steps and tasks based on in-call data.
unlimited custom ai insightsprovides extensive and flexible AI-driven call analysis

Questions about Winn.AI

What does Winn.AI do?

Winn.AI gives sales reps real-time AI guidance during sales calls. It provides live coaching, updates the CRM automatically with key information from calls, sends call summaries and follow-up emails afterwards, and generates next steps and tasks from in-call data. It also adapts to changing playbooks and individual rep needs.

How much does Winn.AI cost?

Winn.AI is a paid tool with no free tier. Its Pro Plan costs $39 per seat monthly and includes up to 25 fields of custom CRM updates. The reviewer says teams that need more than 25 fields in their CRM updates may find that limit restrictive.

What platforms does Winn.AI run on?

Winn.AI runs on the web, macOS and Windows. It is built for live use during sales calls and includes over 35 customizable AI-powered talking points for calls, along with AI meeting prep that turns in-call data into next steps.

What are the limitations of Winn.AI?

The reviewer says Winn.AI only supports up to 25 fields in CRM updates, which limits flexibility. It also does not offer unlimited customization options out of the box, so Toolio lists it as not for sales teams with complex customization needs.

How does Toolio score Winn.AI?

Alex scored Winn.AI 3.9 out of 5 after real use, on 3 Oct 2026. The reviewer recommends it for sales teams needing real-time call coaching and automated insights, while noting the 25-field cap on CRM updates and limited advanced customization.

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