WINN.AI: A real-time AI sales assistant that joins calls to provide playbook guidance, capture data, take notes, and automatically update the CRM. Yung Sidekick: An AI assistant that turns therapy session recordings or spoken recaps into structured clinical progress notes for mental health professionals. Here's where each one pulls ahead on pricing, features, and the meetings it suits best.
How Hosiqo compares and tests toolsFinal recommendation
Shortlist WINN.AI when sales reps getting live playbook and objection-handling guidance on calls matters most, and Yung Sidekick when creating treatment plans and client/therapist reports for mental health practices matters most. Trial each on a few real meetings before you commit — the better fit usually shows fast.
A real-time AI sales assistant that joins calls to provide playbook guidance, capture data, take notes, and automatically update the CRM.
An AI assistant that turns therapy session recordings or spoken recaps into structured clinical progress notes for mental health professionals.
WINN.AI is a real-time AI sales assistant built for sales reps, sales leaders, and revenue operations teams who want consistent execution on customer calls. During a meeting, WINN listens to the conversation and shows the rep, in real time, which playbook topics have been covered and which still need to be addressed, surfacing cues, suggested questions, and battle cards so reps stay on message and handle objections consistently. Sales leaders can encode their playbook and align it to common methodologies such as MEDDIC, MEDDPICC, SPICED, Challenger, and BANT so that the same process is reinforced across the whole team. Beyond live guidance, WINN automates the administrative side of selling: it takes notes, captures structured data from the conversation, updates CRM records including custom fields, and can draft follow-up emails and help with meeting preparation. It integrates with CRM and meeting platforms including Salesforce, HubSpot, Zoom, and Google Meet, syncing captured data automatically to reduce manual entry. WINN.AI is positioned as a revenue execution platform that combines real-time meeting coaching with automated note-taking and CRM hygiene, making it best suited to B2B sales teams that run structured discovery and demo calls. Pricing varies by plan. Check the official website for current pricing.
Best suited for
Yung Sidekick is an AI documentation assistant built specifically for mental health professionals such as psychotherapists, psychologists, counselors, and group practices. It captures sessions in three ways: recording online sessions with its built-in tool, uploading existing audio files, or using a "Dictate Recap" feature where the clinician describes the session verbally afterward. From this audio, the platform generates progress notes in multiple clinical formats including SOAP, DAP, BIRP, and GIRP, along with treatment plans and detailed therapist and client reports, plus session transcripts and analytics. The service runs as a web application (app.yung-sidekick.com), and generated reports can be copied or integrated into a clinician's existing clinical software and workflow. It emphasizes privacy and regulatory compliance, stating it is HIPAA, PHIPA, PIPEDA, and GDPR compliant, with a Business Associate Agreement available, end-to-end encryption, and automatic audio deletion after processing. It is aimed at clinicians who want to reduce time spent on administrative documentation while maintaining clinical focus.
Best suited for
WINN.AI is a free tier with paid upgrades (freemium); Yung Sidekick is a free tier with paid upgrades (freemium). Always confirm current pricing on each vendor's site before buying.
| Feature | WINN.AI | Yung Sidekick |
|---|---|---|
| Core capability | Real-time playbook tracking that shows covered and remaining topics during calls | Records online sessions, accepts audio uploads, or generates notes from a spoken Dictate Recap |
| Standout feature | Live cues, suggested questions, and battle cards for handling objections | Generates progress notes in multiple clinical formats (SOAP, DAP, BIRP, GIRP, and more) |
| Team usage | Support for sales methodologies like MEDDIC, MEDDPICC, SPICED, and BANT | Produces treatment plans and detailed therapist and client reports |
| Integrations | Automatic note-taking and structured data capture from conversations | Provides session transcripts and progress analytics |
| Languages & capture | Automated CRM updates, including custom records, plus follow-up email drafting | Notes and reports can be copied or integrated into existing clinical software |
| Best-fit workflow | Integrations with Salesforce, HubSpot, Zoom, and Google Meet | HIPAA, PHIPA, PIPEDA, and GDPR compliance with end-to-end encryption and automatic audio deletion |
WINN.AI
Choose WINN.AI if you need sales reps getting live playbook and objection-handling guidance on calls — strengths include real-time, in-call guidance keeps reps aligned to the sales playbook.
Yung Sidekick
Choose Yung Sidekick if you need automatically drafting therapy progress notes from recorded or dictated sessions — strengths include purpose-built for therapy documentation with multiple recognized clinical note formats.
WINN.AI
Yung Sidekick
It depends on your workflow. WINN.AI is strong for sales reps getting live playbook and objection-handling guidance on calls, while Yung Sidekick is strong for automatically drafting therapy progress notes from recorded or dictated sessions. Both transcribe and summarize meetings.
WINN.AI is a free tier with paid upgrades and Yung Sidekick is a free tier with paid upgrades. Check each vendor's pricing page for the latest plans and free-tier limits.
Often yes: teams combine tools when one handles capture and another handles analysis.
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