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✦ Your AI Chief of Staff

Know exactly what needs you.

Chiefly monitors every message, meeting, call, and connected system — then hands you the short list that actually matters this morning. Less noise. Faster decisions. Nothing important slips.

30-min demoNo credit cardLive in an afternoon
RMDOPNTR+
★★★★★ 4.9 on G2 · trusted by 200+ founders & executives
Chiefly · Daily Briefing
✦ The Morning Brief · 90-second read

Today is about Acme, and about money.

Two revenue matters need you before noon. Your 9:00 review handles both.
2
Critical
4
Meetings
5
Awaiting
2
Opps
Acme renewal at risk — champion quiet
$240K · closes Jun 30
✦ Why: VIP + revenue + deadline ≤ 10d
Second Acme team wants seats
+$60K expansion · fold into the QBR
● 2 critical · 5 important

Alert Center

Every alert explains why it fired — and what to do.
Payment failed — Northwind #4471
$18,400 · net-15 expires today
✦ Why: rule "failed charge > $10K" · Stripe
Notify financeOpen in Stripe
3 tickets past SLA — Northwind
Linked to the failed payment · churn signal
12 open · 2 approvals

Tasks & Approvals

Chiefly creates, delegates, and chases — you approve.
Approve Globex MSA redline Due today
Reply to David — data room ✦ Drafted
Review staff-eng comp exception Approval
Return Northwind AP call Follow-up
✦ Conversation intelligence

Sarah Chen · Acme

One timeline across email, calls & chat — with a draft ready.
VIP · At risk
Champion 14 months · tone cooled after pricing · $240K renewal
✦ Recommended reply
"No pressure — let's use Friday's QBR to make the renewal easy…"
Use & editCreate task
Draft ready
Re-engagement email
Trusted by operators at fast-moving companies
NorthwindGlobexVertexLumen&CoHighpointMeridianAcmeStonebridge NorthwindGlobexVertexLumen&CoHighpointMeridianAcmeStonebridge
Why Chiefly

Not another chatbot. Not another CRM. Not another to-do list.

Those tools wait for you to ask. Chiefly works the other way around — it watches, decides what matters, and comes to you.

A chatbot answers when asked.
Chiefly tells you first
It surfaces what you didn't know to ask about — before it becomes a problem.
A CRM stores what you enter.
Chiefly already knows
It understands every relationship from your real activity — no data entry required.
A task manager holds your list.
Chiefly clears it
It builds the list from what's happening, then drafts, delegates, and follows up for you.
It's the one thing it should be: your chief of staff.
The executive's real job

You weren't hired to monitor seven inboxes.

Information arrives faster than any leader can triage it. The cost isn't time — it's the decision you didn't make because the signal was buried under noise. Chiefly removes the triage so you're left with judgment.

11+
systems a typical exec juggles — email, chat, calls, calendar, CRM, finance, support…
28%
of the work week lost to checking, switching, and chasing status across tools.
1
missed signal — a quiet champion, a failed payment — can cost a quarter.
Capabilities

One system that watches everything — and only speaks when it matters.

Chiefly connects to the tools you already run on, understands what's happening across them, and turns the firehose into a short, ranked, explained list.

Unified communications

Email, calls, SMS, iMessage, Slack, Teams, and voicemail in a single timeline — read, summarized, and ranked by what needs you.

Attention management

A continuously re-ranked queue of what's critical, important, and waiting — so you always know the two things that actually matter right now.

The Daily Briefing

Every morning, a 90-second brief written like a chief of staff prepared it — the day's thesis, the critical items, and a suggested move for each.

Alerts that explain themselves

Every alert carries a plain-language "why" — the rule that fired and the source — plus the action to take. No black boxes, full trust.

Tasks & follow-ups

Chiefly creates tasks from calls and emails, tracks what you're waiting on, routes approvals, and chases delegated work until it's done.

Relationship intelligence

Importance and relationship scores, sentiment trends, and risk indicators on every contact — so a cooling VIP never slips past you.

How it works

Live in an afternoon. Working for you by morning.

1

Connect

Securely link Gmail or Outlook, your calendar, Slack, phone, Stripe, and more — with read-only, scoped permissions.

2

Chiefly watches

It reads across every system continuously, understanding people, deals, money, and deadlines as one picture.

3

It surfaces

The noise is filtered out. What's left is ranked, explained, and packaged into alerts, a briefing, and tasks.

4

You act

Approve a draft, snooze, delegate, or escalate in one tap. Chiefly handles the follow-through and tracks the reply.

Daily Briefing

The morning brief a chief of staff would write.

Not a digest of everything — a judgment about what today is about. Chiefly opens with the day's thesis, ranks the critical few, and attaches a suggested move to each, so you start already decided.

A 90-second read, narrated or written
Critical → Important → Meetings → Opportunities
A one-tap suggested action on every item
This morning
✦ Generated
Acme renewal is slipping
Champion quiet 6 days · $240K closes Jun 30
✦ Suggested: re-engage in today's QBR
Board deck due tomorrow
3 sections still unowned
Second Acme team wants seats
+$60K expansion · fold into the QBR
Alerts & Rules

Alerts you can trust — because they explain themselves.

Chiefly tells you what's wrong, why it flagged it, and what to do. A human-readable rule engine (When · If · Then) lets you tune exactly what breaks through, and quiet hours keep everything but the truly critical out of your evening.

Every alert shows its trigger and source
Snooze, dismiss, escalate, or assign in one tap
VIP, escalation, and quiet-hours rules you control
Alert Center
2 critical
Payment failed — Northwind #4471
$18,400 · net-15 expires today
✦ Why: rule "failed charge > $10K" · source Stripe
Notify financeOpen in Stripe
3 tickets past SLA — Northwind
Linked to the failed payment · churn signal
Communications & Contacts

One timeline. Every channel. Real intelligence.

Chiefly reads across email, calls, and chat to understand each relationship — sentiment, importance, what's owed, and what's at risk — then drafts the reply for you to approve.

Conversation summaries & recommended replies
Relationship & importance scores per contact
Risk indicators before a relationship cools
Sarah Chen · Acme
VIP · At risk
✦ Conversation intelligence
Champion for 14 months. Tone cooled after the pricing email; mentioned a reorg. $240K renewal, closes Jun 30.
✦ Recommended reply
"No pressure at all — let's use Friday's QBR to make the renewal easy, and fold in the second team's seats…"
Use & editCreate task
0hrs
reclaimed per leader, per week
0days
earlier detection of revenue risk
0
VIP messages left unanswered
0+
systems unified into one view
Enterprise-grade by default

Built for the people with the most to protect.

Chiefly sees your most sensitive information, so security isn't a feature — it's the foundation. Granular, scoped, auditable, and private. Your data is never used to train foundation models.

✓ SOC 2 Type II✓ GDPR✓ Data residencyVisit the Trust Center →
SSO & SCIM
SAML/OIDC single sign-on with automated user provisioning.
Encryption everywhere
AES-256 at rest, TLS 1.2+ in transit, isolated per-tenant keys.
Granular permissions
Role-based access & per-connection read scopes you control.
Audit & retention
Full audit logs and configurable retention per data type.
Connections

Plugs into the stack you already run.

Connect in clicks. Add more anytime. Chiefly only ever reads what your rules allow.

Customers

Leaders who stopped chasing and started deciding.

★★★★★
8+ hours back every week

"By the time I sit down, the two things that matter are already on my screen — with a draft attached. The first tool that reduced my load instead of adding to it."

RM
Rachel Morgan
COO · Vertex (Series C SaaS)
★★★★★
Saved a $240K renewal

"Chiefly caught a renewal going cold six days before my team noticed. That one alert paid for the year. The 'why' on every alert is what earned my trust."

DO
David Okonkwo
CRO · Meridian Software
★★★★★
Runs 3 companies, drops nothing

"I run three businesses. Chiefly is the only reason I'm not dropping balls across all of them. The morning brief reads like my best chief of staff wrote it."

PN
Priya Nair
Founder & CEO · Highpoint
Pricing

Priced for the value of one decision you'd have missed.

Start with a 14-day trial. Scale across the leadership team when you're ready.

Team
For a founder or a small leadership team getting their time back.
$80 / seat / mo
  • Daily briefing & alert center
  • Unified communications
  • Up to 8 connections
  • Core skills & rules
Start free trial
No credit card required
Business
For leadership teams that run on shared context and follow-through.
$140 / seat / mo
  • Everything in Team
  • Call center & recording
  • Skill marketplace & automation
  • SSO · advanced permissions
  • Priority support
Book a demo
14-day trial · cancel anytime
Enterprise
For organizations with security, scale, and compliance needs.
Custom
  • Everything in Business
  • SCIM · audit logs · data residency
  • Custom skills & connections
  • Dedicated success manager & SLA
Contact sales
Tailored to your org
Questions

Everything you'd ask before a demo.

How long does setup take?
Most teams are live the same afternoon. You connect your tools with read-only, scoped permissions, and Chiefly produces your first briefing the next morning. No migration, no data entry.
Is my data secure — and used to train AI?
Your data is never used to train foundation models. Chiefly is SOC 2 Type II, encrypts data with AES-256 at rest and TLS in transit, isolates tenants, and gives you granular per-connection read scopes, audit logs, and configurable retention.
How is this different from my CRM or assistant?
A CRM stores what you enter and a chatbot answers when asked. Chiefly works proactively — it watches every system, understands relationships and risk on its own, and brings you the short list that matters with an action attached. It's a chief of staff, not a database.
Which tools does it connect to?
Gmail, Outlook, Google Calendar, Slack, Teams, Stripe, QuickBooks, Zendesk, Salesforce, Telnyx, Notion, HubSpot, and more — with new connections added every month. Enterprise plans support custom connections.
Can my whole leadership team use it?
Yes. Chiefly supports shared workspaces with role-based access, delegated tasks, and approvals — so context and follow-through are shared across your team while each person sees their own prioritized view.
Is there a trial?
Team plans start with a 14-day free trial, no credit card required. For Business and Enterprise, we run a guided pilot connected to your real stack so you can feel the value before committing.

Meet your chief of staff.

A 30-minute demo, then a guided pilot connected to your real stack. You'll feel the difference on the first morning.

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Meet your AI chief of staff.
Live in an afternoon · no credit card
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