For owner-run businesses with targets to hit
We grow your business. And handle everything else.
An AI team that grows your business, rooted in your data. It learns your numbers, your market and your goals, builds a roadmap, then expert agents do the work across marketing, sales, finance and operations. It scales with you, from startup to enterprise. No tech skills needed. Set up in 20 minutes, your first brief tomorrow morning.
- Meet your AI team: a whole team of experts, working for you tomorrow
- No migration: keep your tools
- Read-only until you say otherwise
- No setup fees, no card to start
Tomorrow, 7:02 AM
ExampleGood morning, Maya.
Your team worked overnight. One thing needs you, about two minutes.
DoneSorted 212 emails and drafted 9 replies
Done by Emma (AI)
DoneFound 11 empty nights next month
Done by Dana (AI)
- Done
Updated your weekly sales report
Done by Dana (AI)
Offer 10% off next month's weeknights to 46 past guests
Sienna (AI), from your bookings and last year's repeat rate: about 6 nights filled.
Sample business. Violet waits for your yes; teal is done.
Before and after
Before Chieffly, and with it
Less doing. More growing.
Strategy
Before: Guessing what to work on next
With Chieffly: A roadmap built from your own numbers, every step backed by data
Help
Before: Doing it all yourself, or juggling freelancers
With Chieffly: One chief of staff coordinating a whole team of experts
Speed
Before: A new website or system takes months
With Chieffly: Built and connected in days
Tools
Before: Apps that don't talk to each other
With Chieffly: Systems connected or replaced, and yours to keep
Quality
Before: Mistakes found by your customers
With Chieffly: Every job checked by a second expert first
Insight
Before: Not sure what's working
With Chieffly: A morning brief and a live scoreboard for every goal
Growth
Before: Hiring when busy, cutting when slow
With Chieffly: A team that grows and shrinks, at one flat price
Over time
Before: The same tools on day 300
With Chieffly: A team that keeps learning your business
Safety
Before: AI tools with unclear access and no record
With Chieffly: Your data walled off, your OK on what matters, every action logged
Your data
Before: Scattered across apps, inboxes and sheets
With Chieffly: Organized in one place, powering your decisions, always yours
Other tools give you agents. Chieffly gives you the whole system: a coordinated team built around your goals.
See it
What you'll actually use
Chieffly · Roadmap
Foundation · Days
- Tools connected · MonDone
- Baseline set · TueDone
Build · Days
- Booking page live · ThuDone
- Automation on · FriWaiting for your yes
Launch · Days to weeks
- Campaign live · Next wkPlanned
Results · Weeks to months
- Early signs · Wk 2–4Planned
- Goal +10% · Month 3Planned
Chieffly · Approvals
Send the spring offer to 212 past customers?
Recommended by Sienna · based on your last 2 years of bookings
- Approve
- Change
- Not now
Chieffly · Goals
More direct bookings
9% → 15% of revenue
Grow revenue
+7% → +12%
Win back my week
14 → 10 admin hours
Example screens with a sample business.
Chieffly in one sentence
A whole team of AI experts, for less than the cost of one employee.
You tell us your goals
Talk, type or upload. About 20 minutes.
Your AI team does the work
Marketing, sales, IT, finance and admin.
You approve with one tap
About ten minutes a day.
What makes us different
Personalized, data-driven decisions for your business, your industry and your market.
No generic advice. Every recommendation shows the data behind it.
Inward signals
Your own data
Sales, bookings, finances, customer messages and reviews.
Outward signals
Your market
Competitors, seasonality and industry trends.
Expert judgment
Pro playbooks
Turn the signals into decisions tied to your goals and roadmap.
How we decide
Signals
Next month is 11 nights behind last year. Nearby rates are down.
Data: Your booking calendar, local market rates
Insight
The gap is midweek. Weekends are on track.
Data: Compared with your past three years
Recommendation
Send a midweek offer to past guests. Expected: about 6 nights filled.
Data: Industry playbook, your goal
Results
Booked nights tracked every week against the goal.
Data: Your booking calendar, weekly
Example from a sample vacation-rental business.
Your team keeps the business running. Who's growing it?
More revenue. More automation. Targets reached.
The busywork comes off your plate, so you can focus on what matters most: growing your business and serving your customers.
Targets keep slipping
Revenue and growth goals lose to the day-to-day, quarter after quarter.
No marketing expertise
Campaigns, ads, SEO and content need specialists you don't have.
No IT department
Your tools don't talk to each other, and every integration needs someone technical.
Good people, stuck on repeat
Your team spends its day on work a system should do, instead of on customers.
Why Chieffly
Every option today leaves you as the glue
AI assistants advise but don't do the work. People are expensive and do one thing. Point tools each solve one slice and don't talk to each other. Chieffly is a whole team that knows your business, works from your data and asks before anything important, for one flat price.
| What you need | AI assistants | Hiring people | Point tools | Chieffly |
|---|---|---|---|---|
| Does the work | Advises | Yes | One task | Yes |
| Knows your business and data | No | Over time | Its slice | Yes |
| Connects your tools | No | Rarely | No | Yes |
| Checks work, asks before acting | No | Varies | No | Always |
| Cost | Low | High | Adds up | One flat price |
For larger companies
One intelligent layer across all your tools
Dozens of costly point tools that don't connect, with insight trapped in each. Chieffly maps your tools, data, processes and people, builds a roadmap to keep, connect, replace or add tools (which can cut software cost), connects them so signals flow to one place, and turns them into clear recommendations for leadership.
Reach out for detailsWhat repetitive work is costing you
Set your own numbers. This is your time only, before any missed revenue.
Hours a week you and your team spend on repetitive work
What an hour of that time costs
Spent on work a system could do, every month
$4,333
- Automate a third of it
- $1,444
- Chieffly Growth
- $499
Automating a third of it frees time worth about 2.9 times what the Growth plan costs.
Your estimate: hours × hourly cost × 52 weeks ÷ 12 months. Nothing you enter here is saved or sent.
Why nothing has fixed it yet
Hiring
Expensive, slow to find, and one person can't cover finance, marketing, sales and IT.
More software
Every new system means a migration, training, and one more login to run.
AI chat
Good answers, but you still do the work, every time, from scratch.
Chieffly
A team that does the work, on the tools you already have, toward the goals you set.
Value by tomorrow, not next quarter
Twenty minutes of your time today. After that, about ten minutes a day to approve what matters. Results are measured in weeks, against the goals you set.
Today · 20 minutes
Pick a goal, tell us about your business
Talk or type about your business and your goals. Once you choose a plan, connect your tools, read-only.
Tomorrow · 9:00 AM
Your first brief and quick wins
What needs you, what slipped, where money is leaking, replies drafted.
Week 1
Your goal starts moving
Roadmap approved, first tasks done, your baseline measured.
Day 30
Measured progress
Results against your goal, and your first repeat job turned into a tool you own.
No migration. Nothing to learn.
Chieffly works on top of what you already run. Nothing gets replaced on day one, nobody retrains, and every connection starts read-only. When a tool is holding you back, your roadmap says so, and you decide.
Connects first to
- Gmail
- Outlook and Microsoft 365
- Calendars
- QuickBooks, read-only
- HubSpot
- Canva
- More every month
Everything ties back to your goals and your roadmap
You set your goals and how you'll measure them. Your team builds the roadmap to reach all of them, does the work and reports progress every week. Every task names the goal it serves.
Your goals
- More direct bookings9% → 15% of revenue
- Grow revenue+7% → +12% vs. last year
- Win back my week14 → 10 admin hours
Your roadmap
- P1 Direct booking engineIn progress
- P2 Automated invoices and statementsDone
- P3 Reviews and AI searchNext
Example with a sample business.
Meet your AI team
Every department you need. Every one an expert.
You talk to Charlie, your chief of staff. Each job goes to the expert who knows it, and someone else checks the work before it reaches you. Archie builds your roadmap, Kai keeps the whole team learning, and Sasha keeps your data safe.
Agentic AI: a team that acts, not just answers.
Charlie AI
Chief of staff
Your one point of contact. Plans the work, sends it to the right expert, checks it before it reaches you.
Archie AI
Strategy and roadmap
Turns your goals into a roadmap, then keeps it on track as results come in.
Emma AI
Executive assistant
Inbox, calendar, travel and your morning brief.
Marco AI
Marketing and advertising
Campaigns, ads, content, SEO and AI search, reviews.
Sienna AI
Sales and pricing
Offers, pricing strategy, pipeline and follow-ups.
Fiona AI
Finance back office
Statements, invoices, cash and tax prep.
Ivan AI
IT, website and automation
Your hosted website, integrations and custom tools.
Dana AI
Data and reporting
Dashboards that measure everything against your goals.
Leo AI
Legal and compliance
Contracts, renewals and deadlines tracked. Not legal advice.
Sasha AI
Security
Protects your data and reports to you directly.
Kai AI
Keeps the team learning
Turns every job and every correction into better playbooks, tested before use.
Harry AI
Keeps the team the right size
Brings in specialists when work peaks and lets them go when it is done.
Cora AI
Customer care
Looks after your customers on your channels, in your voice, and hands over to a person when needed.
Priya AI
Project manager
Plans every step, keeps dates honest and tells you early when something slips.
Theo AI
Product manager
Turns what you need into clear specs for every system the team builds.
Quinn AI
Data manager
Keeps one trusted source for every number and your data clean and safe.
+ a growing team of specialists who join when you need them, and step back when you don't.
Experts, not generalists
Each expert follows a pro's rulebook, learns your business from you and your team, and gets every job checked.
- A professional playbook for every field
- Your own know-how, from you and your team
- Checked by a second expert before it reaches you
- Keeps learning: every job and every correction makes the team better, and every change is tested first
A team that grows and shrinks with your work
Launching a campaign or a new website? Your experts bring in specialists for the job and let them go when it's done. You never pay for idle staff: one flat monthly price, however busy it gets.
- 9May
- 11Jun
- 15Jul (campaign)
- 10Aug
- 12Sep (reviews)
- 9Oct
Your team is AI. Names and faces make them easy to work with, and you can rename them. Messages to your customers go out in your business's name.
Always improving
A team that keeps learning your business
Kai AI
Kai, your team's learning expert, turns every job and every correction into a better playbook. Every change is tested before it reaches you, so your team gets sharper every month. Your private data never leaves your account.
Work
Every job your team does for you
Feedback
Your yes, no and edits
Lessons
What worked and what didn't
Better playbooks
Every expert improves, tested before use
Why you can trust the work
Why it works better than "just using AI"
Like hiring a seasoned pro who already knows your business, on day one.
01
A pro's rulebook
Each expert follows a playbook written and checked by real specialists.
02
It learns your business
Charlie interviews you and your team, so nothing starts generic.
03
Every job is double-checked
A second expert reviews the work before you see it.
04
Smarter every month
What works for one business improves the playbooks for all, without sharing anyone's data.
Built for you. Owned by you.
Everything lands in your portal as its own tab, with settings you change yourself. No developer, no waiting.
A hosted website
Built, hosted and kept current, with booking or checkout that converts. Included on every plan.
Automations
Reminders, statements, follow-ups and reports that run on their own.
Custom tools
A CRM, a pricing tool, a dashboard: whatever your goals need. Bigger builds quoted, after your yes.
Everything built for you is yours.
- Built for your business, not rented by the seat
- No extra subscriptions to stitch together
- Scales as you grow and stays yours
It only does what you allow
Pick a starting style: cautious, balanced or hands-off. Change any setting later.
- Spending limits by category, per item, week and month.
- Backup approvers when you're away. Silence never counts as a yes.
- A pause button for one agent or the whole team.
- Your data walled off, with an independent security agent watching every connection.
| Kind of action | What the team does |
|---|---|
| Research and drafts | Act alone |
| Calendar holds | Ask first |
| Emails sent as you | Ask first |
| Writing to your accounting | Never |
Trust and security
Your data stays yours
Walled off
Each client in its own locked space. Never shared with other clients.
Read-only to start
Nothing changes in your tools until you allow it.
You approve
Important actions wait for your yes. A timeout is never a yes.
Full audit trail
Every action logged: who, what, when and why.
No passwords stored
We never keep passwords, codes or full card numbers.
Always yours
Your data is always yours. Export it anytime.
A whole team for less than one agency
The whole team on every plan. Start free with your roadmap preview. No setup fees, month to month, and two months free when you pay yearly.
Roadmap preview
Free
Your goals, your map and the shape of your plan.
Essentials
$299/ month
1 business, 2 users
For getting your team in place.
The whole AI team, your portal and a hosted website. Help whenever you reach out.
Most owners start here
Growth
$499/ month
1 business, 5 users
For actively growing.
Everything in Essentials, plus new automations and tools built every month, a larger AI and voice allowance, faster support and a quarterly review with a real person.
Portfolio
$999/ month
Up to 3 businesses, 15 users
For owners with several businesses.
Each business walled off, one login, Vera's insights across them all, priority support and a deeper quarterly strategy review.
Enterprise
Let's talk
For many units, departments and regions.
Single sign-on, approvals by department, your data region or a dedicated environment, your own experts and rules, service levels.
Extra users $25 a month; people who only view reports are free. Extra businesses on Portfolio $249 a month. Larger builds are quoted per step, after your yes.
We're opening Chieffly to a first group of businesses. Every plan button joins the waitlist; no payment is taken.
Hiring the experts yourself is expensive. In the US, the median marketing manager earns about $13,900 a month, a financial manager about $13,900 and an IT manager about $14,600, before benefits. Source: U.S. Bureau of Labor Statistics, May 2025. Checked 2026-10-18.
See the figures and sources
| Role | Median a year | About a month |
|---|---|---|
| General and operations managers | $105,770 | $8,800 |
| Marketing managers | $166,790 | $13,900 |
| Financial managers | $166,570 | $13,900 |
| Computer and information systems managers | $175,140 | $14,600 |
| Bookkeeping, accounting and auditing clerks | $50,670 | $4,200 |
| Executive secretaries and executive administrative assistants | $76,590 | $6,400 |
Monthly figures are the annual median divided by 12, rounded to the nearest $100. Salaries only; benefits, taxes and recruiting are not included.
Questions owners ask
How much of my time does this take?
About 20 minutes to start, then roughly ten minutes a day to approve what matters, plus a short weekly digest.
Do I have to switch any software?
No. Chieffly connects to what you use today, read-only to start. If a tool holds a goal back, your roadmap says so and you decide.
What will it do without asking me?
Only what your settings allow. By default it researches, drafts and keeps records, and asks before anything goes out, gets bought or changes live.
Can the AI make mistakes?
Yes. Any AI can be wrong, so we built Chieffly so its mistakes get caught before they cost you anything. Recommendations come from your own data and named sources, and each one says what it used; if there isn't enough data, the team says so instead of guessing. A second expert checks the work, and numbers are calculated by tools, not estimated. Anything public, financial or hard to undo waits for your yes. Spending limits and your never-rules cap the risk, every action is logged, and we track how often you correct the team so it gets better over time.
Will I ever talk to a real person?
Yes. Real people at Chieffly are a message away on every plan. On Growth and Portfolio, a person meets you every quarter to review results, goals and your roadmap. This isn't set-and-forget.
Is my data safe?
Each client's data is walled off, and agents never see passwords or card numbers. Chieffly support can view your account read-only to help you. Every look is logged with a reason, and nothing changes without your invitation.
Are Charlie, Marco and the others real people?
No. They are AI experts with names and faces so they're easy to work with, and you can rename them. Our human team sets them up, reviews the high-stakes work and is there when you need a person.
How does my team learn my business?
Charlie interviews you, and anyone you choose, a few questions at a time: type, talk, chat or just upload what you already have. Each answer goes to the expert it helps, and you see what each one knows.
What if I want to stop?
Every plan is month to month. You can pause or cancel any time, and you keep read-only access for 90 days to export everything and take over what we built for you.