THE STRATEGIC PARTNER
Your AI Chief of Staff. Fully Autonomous.
Your AI Chief of Staff. Fully Autonomous.
Your AI Chief of Staff. Fully Autonomous.
ChiefOS is a fully autonomous AI Chief of Staff that connects to your tools, learns your workflows in 24 hours, and drives execution without being asked.
A Note From The Team
I spent 10 years as Chief of Staff, first at a global VC overseeing 400+ portfolio companies, then on the founding team at a YC startup. I watched the same operational chaos repeat across hundreds of companies: CEOs drowning in follow-ups, critical initiatives stalling, and strategic priorities getting buried under daily fires.
After interviewing 300+ startup CEOs and Chiefs of Staff, one pattern was clear: everyone needs this role, but few can afford it. So I built ChiefOS, the AI Chief of Staff I wish I'd had.
ChiefOS doesn't just answer questions like other AI assistants. It proactively catches stalled projects, flags missed deadlines before they hit your radar, and auto-drafts strategy briefs from your scattered metrics. It's not reactive AI. It's predictive operations. It's trained on 12 million tokens of real startup workflows and powered by thousands of real-time data points specific to your company, learning your unique operating rhythm in 24 hours.
ChiefOS gives founders Chief of Staff leverage, delivered as AI.
I spent 10 years as Chief of Staff, first at a global VC overseeing 400+ portfolio companies, then on the founding team at a YC startup. I watched the same operational chaos repeat across hundreds of companies: CEOs drowning in follow-ups, critical initiatives stalling, and strategic priorities getting buried under daily fires.
After interviewing 300+ startup CEOs and Chiefs of Staff, one pattern was clear: everyone needs this role, but few can afford it. So I built ChiefOS, the AI Chief of Staff I wish I'd had.
ChiefOS doesn't just answer questions like other AI assistants. It proactively catches stalled projects, flags missed deadlines before they hit your radar, and auto-drafts strategy briefs from your scattered metrics. It's not reactive AI. It's predictive operations. It's trained on 12 million tokens of real startup workflows and powered by thousands of real-time data points specific to your company, learning your unique operating rhythm in 24 hours.
ChiefOS gives founders Chief of Staff leverage, delivered as AI.
Steven Callaway, Founder
BENEFITS
Why Choose Us?
Why Choose Us?
Replaces status dashboards and manual reporting with autonomous execution.
Real-Time Intelligence
Access accurate, real-time data to drive smarter decisions across teams faster and more consistently.
Real-Time Intelligence
Access accurate, real-time data to drive smarter decisions across teams faster and more consistently.
Real-Time Intelligence
Access accurate, real-time data to drive smarter decisions across teams faster and more consistently.
Autonomous Execution
Drives follow-ups, assigns owners, and efficiently closes loops without manual input.
Autonomous Execution
Drives follow-ups, assigns owners, and efficiently closes loops without manual input.
Autonomous Execution
Drives follow-ups, assigns owners, and efficiently closes loops without manual input.
Strategic Intelligence
Auto-drafts board updates, strategy briefs, and priority reports from your meetings and metrics.
Strategic Intelligence
Auto-drafts board updates, strategy briefs, and priority reports from your meetings and metrics.
Strategic Intelligence
Auto-drafts board updates, strategy briefs, and priority reports from your meetings and metrics.
SERVICES
Your AI Chief of Staff, Built for Action
Run operations, align teams, and drive execution — automatically.
Cost Management
Payment reminder
Employee Tracking
Social media post
Executive Workflows
ChiefOS catches stuck deals, auto-drafts strategy briefs, and flags risks before they become fires.
Cost Management
Payment reminder
Employee Tracking
Social media post
Executive Workflows
ChiefOS catches stuck deals, auto-drafts strategy briefs, and flags risks before they become fires.
Cost Management
Payment reminder
Employee Tracking
Social media post
Executive Workflows
ChiefOS catches stuck deals, auto-drafts strategy briefs, and flags risks before they become fires.
Always-On Operations
Connects to Slack, Gmail, Notion, Jira and Calendar. Learns your startup in 24 hours, then proactively manages strategic priorities and executive workflows—without waiting for instructions.
Always-On Operations
Connects to Slack, Gmail, Notion, Jira and Calendar. Learns your startup in 24 hours, then proactively manages strategic priorities and executive workflows—without waiting for instructions.
Always-On Operations
Connects to Slack, Gmail, Notion, Jira and Calendar. Learns your startup in 24 hours, then proactively manages strategic priorities and executive workflows—without waiting for instructions.
Research anything...
Research
Software & App Industry
UX & UI Design Industry
High Converting Customer
Strategic Command Center
Replaces status meetings and manual reports with autonomous execution tracking and board-ready updates.
Research anything...
Research
Software & App Industry
UX & UI Design Industry
High Converting Customer
Strategic Command Center
Replaces status meetings and manual reports with autonomous execution tracking and board-ready updates.
Research anything...
Research
Software & App Industry
UX & UI Design Industry
High Converting Customer
Strategic Command Center
Replaces status meetings and manual reports with autonomous execution tracking and board-ready updates.
Code
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Enterprise-Grade AI
Private deployment. SSO and role-based access. Audit trails. Data stays in your environment.
Code
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Enterprise-Grade AI
Private deployment. SSO and role-based access. Audit trails. Data stays in your environment.
Code
1
2
3
4
5
Enterprise-Grade AI
Private deployment. SSO and role-based access. Audit trails. Data stays in your environment.
AI Strategic Ops Partner
Validated by 300+ CEO and Chief of Staff interviews. In pilots, teams report faster decisions and fewer meetings.
AI Strategic Ops Partner
Validated by 300+ CEO and Chief of Staff interviews. In pilots, teams report faster decisions and fewer meetings.
AI Strategic Ops Partner
Validated by 300+ CEO and Chief of Staff interviews. In pilots, teams report faster decisions and fewer meetings.
FEATURES
All features in one place
Your Autonomous Chief of Staff Toolkit
Execution Automation
Handles follow-ups, status checks, and reports so priorities never stall.
Execution Automation
Handles follow-ups, status checks, and reports so priorities never stall.
Execution Automation
Handles follow-ups, status checks, and reports so priorities never stall.
Workflow Orchestration
Runs multi-step processes across Slack, Gmail, Notion, and Calendar automatically.
Workflow Orchestration
Runs multi-step processes across Slack, Gmail, Notion, and Calendar automatically.
Workflow Orchestration
Runs multi-step processes across Slack, Gmail, Notion, and Calendar automatically.
Live Intelligence
Surfaces live insights across your stack so leaders act faster.
Live Intelligence
Surfaces live insights across your stack so leaders act faster.
Live Intelligence
Surfaces live insights across your stack so leaders act faster.
Risk and Escalations
Detects blockers early and nudges owners with clear next steps.
Risk and Escalations
Detects blockers early and nudges owners with clear next steps.
Risk and Escalations
Detects blockers early and nudges owners with clear next steps.
Company-Specific Tuning
Fine-tuned to your data to mirror how your team works.
Company-Specific Tuning
Fine-tuned to your data to mirror how your team works.
Company-Specific Tuning
Fine-tuned to your data to mirror how your team works.
Performance Tracking
Measures impact with live KPIs and progress on every initiative.
Performance Tracking
Measures impact with live KPIs and progress on every initiative.
Performance Tracking
Measures impact with live KPIs and progress on every initiative.
INTEGRATIONS
Seamless Integrations
Seamless Integrations
ChiefOS plugs into your stack to create a unified, intelligent workflow with no extra setup and no wasted time.
Your AI Chief of Staff works where you already work, across every tool your team uses.
FAQ'S
Frequently Asked Questions
Find quick answers to the most common questions about ChiefOS.
Still Have Questions?
We are here to help. Feel free to reach out anytime.
How is ChiefOS different from Slack bots or other AI assistants?
ChiefOS acts autonomously like a real Chief of Staff. It flags risks, drives execution, and drafts strategy updates without waiting for prompts. Built specifically for startup executive teams, not general productivity.
Do I need technical knowledge to use ChiefOS?
No. ChiefOS is designed to work out of the box with a simple setup process.
Can you integrate with our existing tools?
Yes. ChiefOS connects to your current tools so you can keep working in the systems you already know.
What startup stage is ChiefOS built for?
ChiefOS is designed for startups with 10-200 employees who need executive operations but can't afford a full-time Chief of Staff. Perfect for post-seed through Series A companies.
How does the 24-hour learning process work?
ChiefOS analyzes your Slack, email patterns, meeting notes, and project data to understand your workflows, team dynamics, and business priorities. All processing happens in your secure environment.
FAQ'S
Frequently Asked Questions
Find quick answers to the most common questions about ChiefOS.
Still Have Questions?
We are here to help. Feel free to reach out anytime.
How is ChiefOS different from Slack bots or other AI assistants?
ChiefOS acts autonomously like a real Chief of Staff. It flags risks, drives execution, and drafts strategy updates without waiting for prompts. Built specifically for startup executive teams, not general productivity.
Do I need technical knowledge to use ChiefOS?
No. ChiefOS is designed to work out of the box with a simple setup process.
Can you integrate with our existing tools?
Yes. ChiefOS connects to your current tools so you can keep working in the systems you already know.
What startup stage is ChiefOS built for?
ChiefOS is designed for startups with 10-200 employees who need executive operations but can't afford a full-time Chief of Staff. Perfect for post-seed through Series A companies.
How does the 24-hour learning process work?
ChiefOS analyzes your Slack, email patterns, meeting notes, and project data to understand your workflows, team dynamics, and business priorities. All processing happens in your secure environment.
FAQ'S
Frequently Asked Questions
Find quick answers to the most common questions about ChiefOS.
Still Have Questions?
We are here to help. Feel free to reach out anytime.
How is ChiefOS different from Slack bots or other AI assistants?
Do I need technical knowledge to use ChiefOS?
Can you integrate with our existing tools?
What startup stage is ChiefOS built for?
How does the 24-hour learning process work?
Reach out anytime
Ready to Run Your Startup Like a Pro?
Join 20+ Startup CEOs in Private Beta. Get the strategic partner you need but can't afford to hire. Our next cohort starts in 6 weeks. Limited spots available.
Reach out anytime
Ready to Run Your Startup Like a Pro?
Join 20+ Startup CEOs in Private Beta. Get the strategic partner you need but can't afford to hire. Our next cohort starts in 6 weeks. Limited spots available.
Reach out anytime
Ready to Run Your Startup Like a Pro?
Join 20+ Startup CEOs in Private Beta. Get the strategic partner you need but can't afford to hire. Our next cohort starts in 6 weeks. Limited spots available.