Founding Cohort First three Sprints at $2,500 through June 22 — standard pricing $3,500 thereafter. Claim a spot →
Operations infrastructure · $1M–$10M

Stop being the bottleneck in your own business.

Founder-led businesses hit a wall where everything routes through the operator. I build the operations infrastructure that takes the work off your desk — owned by your team, so the value compounds instead of leaving when I do.

Book a 15-minute fit call → See engagement tiers
4–6 weeksDiscovery to live systems
Pay nothingUntil scope is written and approved
1–2 / moNew workflows shipped on Retain
Positioning · 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 be falling on you, and you don't have time to figure out the right tools or workflows on your own.

You don't need another course or another SaaS. You need someone to come in, map your operation, build the systems that take the work off your desk, and keep them running once they're live.
Approach · What I do

Built inside your business.

I build operations infrastructure inside your business. This is not generic automation. The systems are designed around how you actually run the company, owned by your team and built to outlast the engagement.

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 $1M–$10M 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 4–6 weeks instead of months. The systems are simple enough that your team runs them after we leave. That's the only metric that matters.

Founder · PAINGWiN Book a 15-min call rooks@paingwin.com
Engagement tiers

How we work together.

Most clients start with Build.

Tier Zero · Sprint

Sprint

Thirty days to operator capacity.

For operators who need to upgrade themselves before they upgrade the business. Four weeks of focused one-on-one work. You leave with a personal operating manual and the capacity to run your day differently.

$2,500Founding cohort
4Weeks
4Live sessions
  • Kickoff call to map your current operating reality
  • Four weekly one-hour one-on-one sessions
  • Homework between every session
  • Written operating manual at the end, customized to how you work
  • Async email support throughout
  • Refunded in full after Session 1 if you don't see the path forward
Start here Tier One · Build

Build

A defined scope, delivered in sixty days.

For operators who know exactly where they're stuck and want it fixed in 60 days. Clear cost, clear timeline, clear deliverables.

$7,500–15KInvestment
4–6Weeks
50 / 50Payment
  • Three-day discovery and workflow audit
  • Two to four 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
Tier Two · Retain · Build Phase

Operations Partnership — Build Phase

An active partnership with continuous build.

Backlog is deep and you want momentum. Scope evolves. You're already running operations and want to embed new systems in parallel.

$5,000Per month
1–2Workflows / mo
90Day minimum
  • Active building — 1 to 2 new workflows shipped per month
  • Ongoing optimization of existing systems
  • Async support, response within one business day
  • Monthly working session and quarterly business review
  • Priority access to me directly
  • Build clients roll in at $5,000/mo if signed before the project closes
Tier Two · Retain · Operate Phase

Operations Partnership — Operate Phase

Steady state, lights on.

Systems are in place and you want them tended, not actively expanded. You completed Build Phase or Tier One Build and want continuity.

$2,500Per month
1–2Workflows / qtr
90Day minimum
  • Steady-state maintenance and optimization of existing systems
  • 1 to 2 new workflows per quarter
  • Async support, response within one business day
  • Quarterly business review
  • Step back up to Build Phase any month with 30-day notice
Boundaries · What I don't do

What this isn't.

  • Generic consulting or strategy decks
  • Sales coaching, marketing strategy, growth advisory
  • One-off prompts or tool recommendations
  • "Transformation" projects without specific systems shipped
I build operating infrastructure. That's it.
Process · Engagement shape

Three steps to a signed engagement.

  1. Free 15-minute fit call

    I tell you straight if I can help. If not, I refer you out.

  2. Paid discovery (optional, $1,500)

    Half-day deep dive. The deliverable is a written scope. Credited against Build or the first month of Retain if you proceed within 30 days. Not required for Sprint.

  3. Sprint, Build, or Retain

    Depending on where you are.

Common questions

The objections I hear most.

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 if I'm under $1M? Or over $10M?

Under $1M, the bottleneck is almost always revenue — not operations. You'd waste money systematizing a business that hasn't proven its growth engine yet. I'll refer you to someone better suited.

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

I don't know which tier I need. How do I pick?

You don't. That's what the fit call is for. Fifteen minutes — I'll tell you straight which tier matches your situation, or whether none of them do.

The Paid Discovery exists if you want a written scope before committing, but most operators don't need it. Sprint requires nothing more than the fit call.

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 the Build tier 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.

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

Book the call →
Booking
calendly.com/ypliner/15-minute-meeting
Email
rooks@paingwin.com