Founding Cohort 01 — 1:1, 4 seats, starts Aug 3. Founding rate $2,500 (then $4,500). Claim your seat →
AI-native operations · up to $10M revenue

The AI operating system for founder-led businesses.

Lead your business — stop managing it.

We install an AI chief of staff that runs your day-to-day — it reads your inbox, tracks every project, drafts and escalates, and brings the work to you instead of piling it on your desk.

1:1 · 4 weeks · founding rate $2,500 $4,500 · credits in full toward a Build.

Watch — what I actually build 2 min
What we do

A secure, efficient AI operating system — custom-built for your business, so you can lead it instead of manage it.

What we build

An agent at the center of your business.

Information comes to you. You don't chase it.

One system with a 360° view of how you actually operate — that you talk to like a chief of staff. Because it holds the full context, it can act: work your inbox, keep every project current, escalate what needs you, and turn your meetings into briefs.

  • The full picture. It oversees one source of truth for every project and keeps your boards up to date.
  • It reads and drafts. Works your email, writes the replies, escalates only what needs a decision.
  • It briefs you. Turns meetings and notes into the summary you'd have written yourself.
  • It comes to you. Surfaces what matters, so you stop going looking for it.
Ears your meetings & notes Eyes email, calendar, files Hands your tools + connectors Memory your source of truth THE BRAIN Chief of staff Runs on Claude Cowork
Connects to your stack
+ your CRM
These are just examples — we build into whatever tools you already run on.
The method · 10 / 80 / 10

You do 10%. The system does 80%. You keep the last 10%.

The gap between AI that helps a little and AI that runs your operation is context. We engineer what the agent knows, what it owns, what "done" looks like, and when to escalate — so it carries the heavy middle instead of just autocompleting. You set the direction and make the calls; it does the work in between.

On your own, or with generic AI
You · 40%
AI · 20%
You · 40%
With a context-engineered agent
You
The system · 80%
You

Talk to the rock — don't hit it. You delegate to the agent the way you would a great employee: give it context, a clear objective, and the deliverables — then it does the work and comes back to you. You stop typing and start directing.

Solutions · what we build

Starting points, shaped to your business.

Every build is custom — but most start from one of these. No fixed menu, no set prices; we scope it to whatever's actually slowing you down.

Chief-of-staff agent

Reads your email, books the calendar, keeps meeting notes, holds one source of truth for every project, and updates your boards.

Content automation engine

Curates content, writes its own prompts, and runs the admin — your team just approves and tunes. It reviews itself and flags what needs a human.

Cash-flow & finance dashboard

A live, predictive view of cash, budget, and the accounting picture — instead of waiting on month-end to find out where you stand.

Post & campaign tracker

Tracks every post and campaign across channels automatically, keeps the numbers in one place, and flags what needs attention.

Ask-anything business agent

A 360° agent you talk to — it holds the context, does the chasing and follow-up, and answers on demand instead of you digging.

Meeting-to-brief system

Turns your meetings and notes into briefs, action items, and follow-ups — so nothing said in a room quietly disappears.

Working across media · medical · technology · financial — and more as we go.

Who this is for

The operator is the bottleneck.

You're spending 40-plus hours a week on tasks the business needs but only you can do. You know most of it shouldn't fall on you, and you don't have time to figure out the right tools on your own. You don't need another course or another SaaS — you need someone to build the systems that take the work off your desk, and hand them to your team.

Now enrolling · Founding cohort

Four weeks from manager to leader.

Right now you're managing — every task routes through you. In the founding cohort I work with you one-on-one to build the AI-native systems that absorb the managing. We install the operating system; you learn to run it. You leave leading a business that no longer needs you in the middle of it.

  • One-on-one with me. Private working sessions, built on your real workflows — not a webinar, not a group.
  • We build it — and teach you as we go. You get working systems live in your stack, and the knowledge to extend them yourself.
  • Built for owner-operators running real businesses — property, hospitality, care, services, trades. Not a tech-founder room.
  • Your team runs it after. Same standard as every engagement: if they can't operate it without me, it isn't done.
What we build together
  • Week 1 — Map where your time actually goes. Pick the two workflows worth automating first.
  • Week 2–3 — Build them live in your stack. You watch it get made, so you can change it later.
  • Week 4 — Hand off to your team, document it, and set the next two in motion.
2–4
Weeks to live systems
$0
Until scope is approved
100%
Owned by your team
Engagements · Coach → Build → Partner

Three ways in. One standard.

Learn to build it yourself alongside me, hand me a defined build, or keep me on to ship new systems every month. Every path ends the same way: your AI-native systems live, and your team running them without me.

One · Coach

Founding Cohort

One-on-one with me. We install your AI-native systems and teach you to run them.
$2,500
$4,500 founding rate
4
Weeks
1:1
Format
  • Weekly 1:1 working sessions — build, not lecture
  • Two AI-native workflows live in your stack by week 3
  • Documentation and team handoff in week 4
  • Async support between sessions
  • ~2–3 hours of your time a week
Credits in full toward a Build within 90 days. You leave able to run it yourself.
Two · Build

Build

Done for you. A defined scope, built into your business and live in weeks, not months.
$7,500–15K
Investment
2–4
Weeks
50/50
Payment
  • Three-day discovery and workflow audit
  • Two to four AI-native systems built and live in your stack
  • Operator training so your team runs it without me
  • Documentation and handoff
  • Thirty-day post-launch support
Guarantee: if systems aren't live and your team isn't running them by handoff, I keep working at no extra cost until they are.
Three · Partner

Ongoing Partner

We own your technology development, ongoing — shipping new AI-native systems and maintaining everything already live. Never your day-to-day operations.
$5,000
/mo · active build
$2,500
/mo · oversight
90
Day minimum
  • Active build — 1 to 2 new AI-native systems shipped per month
  • Oversight — my team maintains and refines everything already live
  • We manage your technology; you never manage us
  • Monthly working session, quarterly technology review
  • Priority access — response within one business day
Build clients roll in at $5,000/mo if signed before the project closes.

Not sure where you land? The free 20-minute fit call sorts it — I'll tell you which path fits, or if none of them do.

Also in the works · early access

Managing a team and want to know what's really going on?

We're building proprietary software that turns short, private AI-led conversations with your people into one honest read on where the friction really is — no individual identifiable. It's in early-adopter release right now. If that's interesting, mention it on your call and I'll get you in.

Ask about early access →
Rooks Pliner
Operator · Behind PAINGWiN

I'm Rooks.

I built PAINGWiN after years of watching founder-led businesses outgrow the operator running them. Revenue scales. The operator's calendar doesn't. Eventually every founder-led business hits the same wall: too many decisions, too few systems, no time to build them.

I lead every engagement directly — discovery, scope, and handoff happen with me. A small delivery team supports the build work behind the scenes, which is how we ship complete systems in weeks, not months. The systems are simple enough that your team runs them after we leave. That's the only metric that matters.

Book your 20-minute call → rooks@paingwin.com
Boundaries · What I don't do

What this isn't.

I build operating infrastructure. That's it.

Process · Engagement shape

Three steps to a signed engagement.

01

Free 20-minute fit call

No deck, no pitch. I tell you straight if I can help — and you leave knowing the first one or two things I'd automate for you, whether you hire me or not.

02

Pick your path

Coach, Build, or Partner — whichever matches where you are. On the call I'll tell you which one fits, or if none of them do.

03

Systems live, your team running them

Every path ends the same way. Handoff isn't a document — it's your team operating the thing without me in the room.

Common questions

The objections I hear most.

How is the cohort different from just hiring you for a Build?

Price and depth. In a Build I'm inside your operation doing the work. The cohort is one-on-one, and you do more of the building yourself with me guiding it — you walk away with the knowledge, not just the systems.

It's the right entry point if you want to know whether systems thinking actually changes your week before committing $7,500+. If it does, your $2,500 credits in full against a Build within 90 days.

How is this different from hiring a fractional COO or ops manager?

A fractional COO runs operations day-to-day. I build the infrastructure that makes operations runnable in the first place. After my engagement, your team — or your future COO — owns the systems and runs them without me.

If you already have an ops person and they're drowning, I'm the right call. If you don't have one and don't want one, I build to that constraint.

What size business is this for?

Founder-led businesses up to about $10M. There's no hard floor — if you're the operator buried in work only you can do, the systems pay off whether you're at $400K or $8M. What matters is that you have enough real process to systematize.

Over $10M you usually need a full-time operations leader and a team, not a one-person partner — I'll point you at people who do that work.

Who actually sees the interview answers in the Report?

Nobody in your reporting chain reads individual transcripts. The synthesis only reports a pattern when enough people independently raise it, so no single person is identifiable from what comes back to you. Employees can request erasure of their own transcript at any time, and transcripts are deleted on a set retention clock.

There's one carve-out, and it's stated plainly to every participant before they start: information indicating someone is at risk of harm is escalated. The speaker's identity is still protected — the information is not.

Is my company's data kept separate from other clients?

Yes. Each engagement is isolated — your organisational data is never pooled with another client's, never used to train models, and never surfaces in anyone else's report. If your counsel wants the architecture in writing before you deploy, ask on the call and I'll send it.

What if only half my team responds to the interview?

Fair challenge, and it's the honest limit of any voluntary instrument. Two things make this different from a survey: it's a paid fifteen minutes on the clock, not an unpaid Likert grid on someone's own time, and it's a conversation that adapts rather than a fixed form.

The report also tells you exactly who was invited versus who completed, broken down by team and shift. If participation is thin in one department, you see that — it doesn't get quietly averaged away.

What tools do you build in? Do I have to switch platforms?

I build inside whatever stack you already use — ClickUp, Notion, Airtable, HubSpot, Slack, Zapier, Make, the AI tools, your CRM. I don't sell software and I don't collect referral fees for steering you toward platforms.

If your current stack is genuinely the wrong shape for what you need, I'll say so. Otherwise we work with what you have.

What if my team doesn't adopt the systems after you leave?

Adoption is part of the build, not an afterthought. I don't hand off until your team is running the systems live, on real work, without me in the room.

That's why Build comes with a guarantee: if systems aren't live and being used by handoff, I keep working at no extra cost until they are.

Do you sign NDAs and handle confidentiality?

Yes. Standard NDA available before the fit call if you want one. The work itself touches sensitive parts of your operation — financials, client lists, internal process — so confidentiality is the default, not an upgrade.

Contact · Start a conversation

Let's talk.

Twenty minutes. No deck. I'll tell you whether we should work together by the end of the call.

Book your 20-minute fit call →