Your projects, milestones
& contacts — all in one place.
CheckStay Pro is a focused macOS app for managing project portfolios, tracking risks, and keeping every stakeholder aligned — with a built-in AI assistant that knows your work.
Built for project managers who are tired of bloated team tools and just need a clean command center for their own work.
macOS · Free forever · Pro $49 one-time · Sync coming soon
Early Access Release
CheckStay Pro is currently in early access. Features and workflows may evolve as we incorporate feedback from early users.
CheckStay Pro
Your projects, milestones & contacts — all in one place.
MOC
2 projects
Pinned projects for quick access.
Code
3 projects
The problem
Why CheckStay Exists
Most project management tools were built for teams. They come loaded with collaboration boards, chat threads, permission layers, and notification systems — all of which add real overhead for the individual professional who simply needs to stay on top of multiple projects at once. CheckStay Pro strips that away and puts the project manager back in control.
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Traditional PM tools are built for teams, not individual operators. Boards, sprints, and org-wide dashboards are powerful for teams — but overkill for a solo PM managing a project portfolio.
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Chat systems, permission layers, and collaboration features add unnecessary overhead. You spend more time configuring the tool than using it to manage your work.
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Project managers end up juggling spreadsheets, sticky notes, and multiple disconnected tools. Context lives everywhere — which means it's effectively nowhere.
Everything you need
Project management, without the overhead
Projects & Milestones
Track every project from kickoff to close. Set milestones with due dates, monitor status at a glance, and keep your portfolio organized with categories and focus pins.
RAID Logs
Capture risks, assumptions, issues, and decisions in structured logs. Rate likelihood and impact, assign owners, and link items to milestones so nothing slips.
Stakeholders & Contacts
Maintain a global contacts library and assign stakeholders per project. Names, orgs, emails, and titles — all accessible from wherever you need them.
Calendar & Outlook
See all your milestones on a unified calendar. Integrate with Microsoft Outlook to pull in events and emails, linking them directly to your projects. Requires Pro.
AI Assistant
A built-in AI bot that sees your projects, remembers your preferences, and takes action — create tasks, log decisions, or ask what's overdue. Bring your own API key. Requires Pro.
Activity Log
Timestamped entries for everything that happens across your projects. Link activities to contacts and emails for a full audit trail.
What it does
A Command Center for Project Managers
CheckStay Pro consolidates the essential project management workflows a professional actually uses — into a single, focused desktop application that stays out of your way.
Project Dashboards
See every project's status, milestones, and health at a glance — all in one portfolio view.
Budget Tracking
Track planned vs. actual spend per project without a separate spreadsheet or finance tool.
RAID Log Management
Log risks, assumptions, issues, and decisions — rated, owned, and linked to milestones.
Document Storage
Attach and organize project documents directly inside the app — no more hunting through folders.
AI Assistant
Ask questions about your projects, log decisions, or surface what's overdue — using your own API key.
Outlook Integration
Pull in calendar events and emails from Microsoft Outlook and link them directly to your projects.
Pricing
Simple, honest pricing
Free
$0
Forever
- ✓ Up to 3 projects
- ✓ Up to 6 contacts
- ✓ Milestones & checklists
- ✓ RAID logs
- ✓ Bar timeline view
- ✓ Local storage, offline-first
Pro
Most popular$49
One-time purchase
- ✓ Everything in Free
- ✓ Unlimited projects & contacts
- ✓ AI assistant (bring your own key)
- ✓ Gantt & timeline view
- ✓ Outlook & email integration
- ✓ Categories & reports
Sync is on its way 🚀
We're bringing CheckStay to more platforms — sync launches with them.
Sync
$2.99
/mo
or $24/yr — save 33%
- ✓ Encrypted cloud backup
- ✓ Multi-device sync
- ✓ Restore from anywhere
- Add-on for Free or Pro accounts.
Our story
Built by a Project Manager
CheckStay Pro didn’t start in a product studio. It was built by a working project manager who was spending too much time wrestling with tools designed for engineering teams, and not enough time actually managing projects. After years of patching together spreadsheets, note apps, and calendar hacks to get a clear picture of a project portfolio, the decision was made to build the system that should have existed all along — a focused, desktop-first command center purpose-built for real-world project oversight.
Every feature in CheckStay Pro reflects a genuine need from active project management work. No hypothetical use cases. No bloat added to justify a higher price point. Just the workflows a project manager actually reaches for every day.
Ready to run your projects better?
Start free and upgrade when you need more. One-time purchase, no subscription required for Pro.