Winn.ai
The Sales Execution Platform for real-time AI selling
Overview
Winn.ai's differentiator is timing: instead of reviewing a call afterward, it feeds reps real-time cues while they're on the line, which is genuinely useful for newer reps still internalizing a sales methodology. The playbook tracking against MEDDIC/SPICED/BANT gives sales leaders visibility into process adherence, not just outcomes, and the automated CRM and follow-up work removes a meaningful chunk of post-call admin.
At $69/seat/month billed annually, it's a real commitment for smaller teams, and it competes with a growing field of real-time and post-call assistants (Sybill, Momentum, Gong). Some reps also need an adjustment period to get comfortable with live on-screen prompts during a sales conversation rather than finding it distracting.
Key Features
Real-time talking points: surfaces over 35 smart AI prompts live during the call to guide what a rep should say next.
Playbook tracking: tracks conversations against customizable playbooks built on MEDDIC, SPICED, and BANT frameworks.
Automated CRM updates: writes call data into CRM fields (up to 25 fields on the Pro plan) without manual entry.
Auto-generated follow-ups: creates call summaries and follow-up emails automatically after each meeting.
Meeting prep briefs: AI-generated prep notes before calls based on prior interactions and CRM data.
Integrations: works with Zoom, Microsoft Teams, Slack, Salesforce, and HubSpot.
Pricing
Starting price
From $69/seat/mo (billed annually); Enterprise custom
Pro: $69/seat/mo, billed annually, includes real-time talking points, playbook templates, CRM integration (up to 25 fields), and automated summaries.
Enterprise: custom pricing tailored to larger deployments, contact sales.
Free trial: 14-day trial available on the Pro plan.
Disclaimer: pricing may change, confirm on Winn.ai's own pricing page before buying.
Pros
Live-call coaching: real-time talking points help reps handle objections and stay on script in the moment.
Framework-native: built-in MEDDIC, SPICED, and BANT playbook templates save setup time.
Strong CRM automation: updates up to 25 CRM fields automatically per call on the Pro plan.
Broad integrations: connects cleanly with Zoom, Teams, Slack, Salesforce, and HubSpot.
Cons
Premium price point: $69/seat/month is higher than several notetaker-first competitors.
Learning curve: real-time prompts require reps to adjust their call habits to use effectively.
Single-plan self-serve: Enterprise-level customization requires a custom sales conversation.
What Makes It Unique
Live in-call assistance: unlike most conversation-intelligence tools that analyze calls after the fact, Winn.ai actively feeds guidance to reps while they're still talking.
Kay Score
7.1
/ 10
Tool Information
Pricing
From $69/seat/mo (billed annually); Enterprise custom
Category
Automation & AI Agents
Platform
Web / iOS / Android
Last Updated
