QUICK WIN SPRINT // 14 DAYS

What is the AI Chief of Staff Sprint?

A 14-day Quick Win Sprint where chalkthis. builds you a daily command brief that summarizes your inbox, calendar, follow-ups, and documents, and drafts the next actions for your approval. Manual-first, AI-assisted, approval-only. You keep the system whether you continue with us or not.

Most clients start because they are already losing hours every week to this.

Are you ready to get your time back?

Yes! I want to save 10-15 hours / week! See a sample brief

Try it for 14 days. Keep the system either way.

WE ONLY RUN A LIMITED NUMBER OF PILOTS AT A TIME

Who it's for

Founders, operators, solo professionals.

Agency leads, service-business owners, real estate brokers, consultants. If you spend more than two hours a day moving information around instead of doing the work that actually moves the business, this is for you.

What you get

A daily command brief.

One document in your inbox every morning. Top 3 priorities, emails needing reply, follow-ups due, meeting prep notes, documents to review, draft replies ready for your approval. Fifteen minutes, the day mapped.

How long it takes

14 days, five phases.

Days 1 to 2: workflow audit. Days 3 to 5: build the brief manually. Days 6 to 8: refine categories and tone with you. Days 9 to 11: automate one piece. Days 12 to 14: results report and conversion offer.

What it costs

$500 for the pilot.

Most pilots convert to a $750 monthly retainer with a $1,500 setup fee. No long-term contract. Pause or refund the pilot in the first 7 days, no questions.

Today's Command Brief // Tuesday

1. Approve the draft reply to Sarah at TerraVista about the contract revisions (24 hours overdue).
2. Prep for the 2pm with the Riverside team. Notes below.
3. Follow up with Marcus. He has been waiting 6 days.

Emails needing reply (3)

Sarah, TerraVista, contract revisions. Draft ready, see end.
Lisa, Riverside, proposal feedback. Suggested 4 questions.
Anonymous referral, new lead. Draft warm reply, see end.

Follow-ups due (2)

Marcus, last contact 6 days ago. Draft check-in below.
Penelope, last contact 11 days ago. Draft warm nudge below.

Meeting prep (1 today)

2pm Riverside team. Open items: pricing, timeline, signoff. Their last email is in a buried thread, summary attached.

Documents needing review (1)

Lakeshore proposal v3. 2 changes from v2 flagged. Your decision needed on payment terms.

Draft replies ready

See attached. Approve, edit, or reject.

Owner approval needed

Approve draft reply to Sarah.
Approve check-in to Marcus.
Approve warm nudge to Penelope.
Decision on Lakeshore payment terms.

This replaces hours of scattered work with a single, clear plan.

"We draft. You approve. Nothing leaves your inbox without you."

The chalkthis. operating principle

WHAT WE DON'T DO

Approval-first by design.

Send messages on your behalf without your approval.
Give legal advice or interpret contracts.
Access financial accounts or move money.
Delete or modify production records.
Book appointments unilaterally.
Replace a lawyer, accountant, doctor, or therapist.

PILOT // START HERE

14-day pilot

$500

The fastest way to see if this works for you.

Workflow audit and intake
Daily command brief, manual concierge
Inbox, calendar, and follow-up rules
Convert to retainer or walk away with the system

Yes! I want to save 10-15 hours / week!

PRIORITY BUILD

Setup plus first month

$1,000

For clients continuing after the pilot.

Full Sprint plus first month of retainer
Faster path to automation
For buyers with clear pain and clear budget

Start here

CONCIERGE

Setup plus retainer

$1,500 + $750/mo

For full operational offload.

Sprint setup, ongoing daily brief
Refinement and automation buildout
For post-validation, post-proof clients

Talk to us

AFTER THE SPRINT

Most clients keep going.

After 14 days, most clients continue on the monthly retainer at $750 a month. We add automation, expand scope, and refine the brief based on what is actually moving the needle.

See the pricing

FAQ

Questions we get every week.

Will it send emails on its own?

No. Approval-first by design. The AI Chief of Staff drafts. You approve. Nothing leaves your inbox without you.

What if my inbox is Outlook, not Gmail?

Both supported. We work with whatever you already use.

Do I have to sign a long contract?

No. 14-day pilot, then month-to-month. Cancel any time.

Will you read all my emails?

We see only what you share, scoped through OAuth permissions. No passwords, no full-account access. Raw email data is purged after 7 days. Summaries are kept so the brief stays useful over time.

Can it replace my assistant?

Different tool, similar outcome for admin. An assistant handles context, judgment, and human relationships. The AI Chief of Staff handles the information triage layer that wears assistants out.

Who delivers it?

Joe Lissy at chalkthis. plus AI assistance during the Sprint. The productized agent system takes over from Month 2 onward, with Joe still in the loop for changes and approvals.

What if I don't like it?

You can pause or refund the pilot at any point in the first 7 days, no questions. After that, you keep whatever has been built.

WHAT HAPPENS AFTER YOU START

The 14 days, plain English.

DAYS 1 TO 2

We map your workflow.

DAYS 3 TO 5

We build your first brief manually.

DAYS 6 TO 10

We refine and structure.

DAYS 11 TO 14

You see the system running.

You will know quickly if it is something you want to keep.

APPLY FOR EARLY ACCESS

Apply for the 14-day Pilot.

Three early adopter slots. We respond within 24 hours.