Pricing that scales with your team
Turn every 1-on-1 meeting into a system for performance and growth — with AI-guided meeting intelligence that drives accountability, engagement, and team growth.
Pricing is per Leader (manager). Team members are included free under their Leader's seat (up to 10 team members per leader). Every Leader starts with a 14-day free trial — no credit card, full access, converts to Pro unless cancelled.
Pro
For Leaders who want every 1-on-1 meeting to drive growth and accountability.
Includes a 14-day free trial. Cancel anytime.
Designed for Leaders running real employee check-in programs with consistent accountability, growth tracking, and leadership support.
Seats & access
- 1 Leader seat + up to 10 Team Members included
AI meeting intelligence
- AI-powered meeting prep (Leader-only, transcript upload)
- AI post-meeting analysis, sentiment & themes
- Working Style profiles & tailored conversation guidance
- Team Health intelligence (Satisfaction · Sentiment · Consistency)
- Performance summary reports
Growth & accountability
- Goals with SMART AI feedback + alignment to company objectives
- Action Items with on-time tracking
- Plans: Performance Improvement Plans, Career Plans, Milestones
- Recognition & Kudos with Engagement Leaderboard
Operations & support
- Calendar integration (Google / Outlook) with reports' availability
- Meeting backup & restore
- In-app Help Me / Contact Admin support
Enterprise
For organizations standardizing leadership across teams.
for org-wide pricing.
Built for organizations standardizing leadership development, accountability, and engagement across teams.
All Pro features, plus
Org administration
- Org-wide seat licensing (allocated by your System Admin)
- System Admin & Org Admin roles with strict multi-tenant isolation
- Cross-team visibility for Org Admins
Branding & governance
- Org-level branding (logo, accessible color palette)
- Org-wide governance: meeting topics, schedule templates, defaults
- Immutable audit logging
- Database backup & restore controls
Support & roadmap
- Priority onboarding and dedicated support contact
- Roadmap: SSO via Microsoft Entra ID
Every plan starts with a 14-day free trial. Annual billing saves ~20%.
Why managers choose Winning 1-on-1s™
Reframe meeting software as AI-assisted leadership coaching — built for the conversations that actually drive performance.
AI-powered prep
Personalized briefing before every 1-on-1 — no more blank-page anxiety.
Guided conversations
Structured prompts that eliminate awkward check-ins.
Persistent accountability
Action items and goals carry across sessions automatically.
Engagement insights
Spot disengagement early and reduce turnover.
Working Style intelligence
Adapt your communication style to every team member.
Coaching in the workflow
Leadership coaching embedded directly where you already work.
One-on-Ones that actually drive results
Transform routine check-ins into structured, meaningful conversations that improve performance, accountability, and engagement.