Shortlist by what you need
Start here if you know why you are leaving WINN.AI.
Want the closest match?
VoiceOpsMost similar to WINN.AI in what it does, its category and its price.
Visit (opens VoiceOps in a new tab)Need a free plan?
SilkChartHas a free plan, rated 4.0 out of 5. WINN.AI has none.
Visit (opens SilkChart in a new tab)Want the lowest price?
NutshellFrom $13/mo, the lowest starting price here.
Visit (opens Nutshell in a new tab)Want the best rated?
DemodeskRated 4.1 out of 5 in our review, against 3.9 for WINN.AI.
Visit (opens Demodesk in a new tab)
At a glance
Green means better than WINN.AI, red means worse. Prices are starting prices per month.
| Tool | Our rating | Starts at | Free plan | Best for | Compare |
|---|---|---|---|---|---|
 WINN.AIBaseline | 3.9 | Not listed | No | Coaches a rep through the playbook during the call, then fills the CRM afterwards. | |
| VoiceOps | 3.9Same | Not listed | No | Reads a sales team's recorded calls, measures each rep's skills against the playbook, and prepares the 1:1 brief with the supporting calls attached. | vs WINN.AI |
 Sybill | 3.5−0.4 | Not listed | No | Joins your sales calls to take notes automatically - sign in with your work email, no separate account needed. | vs WINN.AI |
 Attention | 3.6−0.3 | Not listed | No | AI grades 100% of your sales team's calls automatically against MEDDIC or BANT scorecards you build yourself - and the CRM fills itself in after every call, no more chasing reps. | vs WINN.AI |
 Close | 3.8−0.1 | Not listed | No | Chloe, a full AI sales agent built into the CRM, calls leads, qualifies them through real conversation, and books meetings - not a separate bolted-on tool. | vs WINN.AI |
| SilkChart | 4.0+0.1 | Free | YesWINN.AI has none | Grades a sales call against MEDDIC or Challenger, not a generic 'good call' score. | vs WINN.AI |
| Nutshell | 3.7−0.2 | $13/mo | No | Every call and meeting gets automatically transcribed, summarized, and logged - plus Nutshell IQ visitor identification and a 24/7 AI chatbot for lead engagement. | vs WINN.AI |
 PitchMonster | 4.0+0.1 | Not listed | No | Sales reps rehearse against an AI buyer that objects like their real customers do. | vs WINN.AI |
| Demodesk | 4.1+0.2 | $29/mo | No | AI sales agents record, transcribe, and coach live meetings while auto-updating the CRM behind the scenes. | vs WINN.AI |
The alternatives in detail
In order of how closely each one matches WINN.AI.
VoiceOps
3.9Not listed
vs WINN.AISame
Reads a sales team's recorded calls, measures each rep's skills against the playbook, and prepares the 1:1 brief with the supporting calls attached.
- Measures rep skills against the playbook across recorded calls
- Prepares per-rep 1:1 briefs with supporting calls linked
- Tailored roleplays for the specific behaviour needing work
Findings are specific and checkable, not generic sentiment scores
No public pricing - demo and sales conversation only
Sybill
3.5Not listed
vs WINN.AI−0.4
Joins your sales calls to take notes automatically - sign in with your work email, no separate account needed.
- Automatic AI joining of sales video calls
- Automated call note-taking
- Work-email/SSO team account access
Automatic call-joining removes the burden of manual note-taking mid-conversation
Feature depth beyond call-joining and notes wasn't independently verified here
Attention
3.6Not listed
vs WINN.AI−0.3
AI grades 100% of your sales team's calls automatically against MEDDIC or BANT scorecards you build yourself - and the CRM fills itself in after every call, no more chasing reps.
- Call recording/transcription across 100+ languages
- AI Coaching Scorecards grading 100% of team calls against custom frameworks
- Automatic CRM field population after every call
Grading every call, not a sample, surfaces coaching patterns a spot-check misses
No published pricing - enterprise sales process only
Close
3.8Not listed
vs WINN.AI−0.1
Chloe, a full AI sales agent built into the CRM, calls leads, qualifies them through real conversation, and books meetings - not a separate bolted-on tool.
- Chloe - AI sales agent that calls, qualifies, and books meetings
- Automatic CRM field updates from AI-driven conversations
- Call transcription and summarization
Chloe updates the CRM directly, no manual sync step after AI-driven calls
Pricing isn't disclosed on the homepage
SilkChart
4.0Free
vs WINN.AI+0.1Free plan
Grades a sales call against MEDDIC or Challenger, not a generic 'good call' score.
- Call analysis against MEDDIC, Challenger, SPIN and SPICED
- Personalised rep scorecards and objection-handling comparison
- AI Coach feedback immediately after each call
Grades against named methodologies, not a vague AI quality score
Named backers confirm a real seed-stage company, still early
Nutshell
3.7$13/mo
vs WINN.AI−0.2
Every call and meeting gets automatically transcribed, summarized, and logged - plus Nutshell IQ visitor identification and a 24/7 AI chatbot for lead engagement.
- Automatic call/meeting transcription, summarization, and logging
- AI Sales Assistants for follow-ups and email generation
- Nutshell IQ - anonymous website visitor identification
Automatic transcription/logging keeps pipeline notes complete without cutting into selling time
Higher tiers ($42-$79/user/month) required for the deepest AI/automation features
PitchMonster
4.0Not listed
vs WINN.AI+0.1
Sales reps rehearse against an AI buyer that objects like their real customers do.
- AI role-play against your own ideal customer profile
- Phone, screen-share and face-to-face call modes
- 29 languages
Moves the cost of learning off real pipeline
Per-seat annual pricing quoted only after a demo
Demodesk
4.1$29/mo
vs WINN.AI+0.2
AI sales agents record, transcribe, and coach live meetings while auto-updating the CRM behind the scenes.
- AI-generated call transcription and coaching feedback after every meeting
- Automatic CRM updates pulled from call content, reducing manual data entry
- Built-in scheduling with booking links and calendar automation
Automatic CRM updates cut the manual note-taking that follows most sales calls
No perpetual free tier, only a 14-day trial before payment is required
FAQ
Questions people ask
Is WINN.AI free?
WINN.AI does not list a free plan. Check its pricing page for current plans.
What is the best free alternative to WINN.AI?
SilkChart is the highest-rated alternative here with a free plan (4.0 out of 5).
What is the cheapest alternative to WINN.AI?
Among paid plans, Nutshell has the lowest starting price (from $13/mo). If you need it free, start with SilkChart.
How did you pick these alternatives?
We match tools on what they do, their category and their price, using the details in our directory. Ratings come from our reviews and reader reviews.