OUTRIGGER ADVISORY GROUP — AI-Powered Business Operating Systems
If Any of These Sound Familiar

The problems OUTRIGGER was built to solve.

Hover over any card to see the full picture.

01
Disjointed
Nothing connects or works together
Everything is a workaround

OUTRIGGER replaces disconnected tools and manual workarounds with one integrated operating layer — tested, documented, and built to scale.

02
Undervalued
Business worth less than it should be
You deserve a higher multiple

If the business depends on you to run it, buyers pay less. OUTRIGGER installs the systems that make your business worth what you built it to be.

03
No Proof
Investors want traction you cannot show
Activity is not traction

Investors fund proof, not effort. OUTRIGGER builds the automated revenue system and investor-ready reporting your next round requires.

04
Manual Overload
Team drowning in repetitive tasks
Stop doing $20-per-hour work

OUTRIGGER automates the high-volume manual work consuming your team so every hour goes toward growth, not administration.

05
Blind on Cash
No idea what cash looks like in 90 days
Flying blind on your finances

OUTRIGGER BALANCE™ gives you 90-day forward visibility and scenario modeling — so you make every major decision with data, not hope.

06
AI Left Behind
Competitors automating while you watch
The gap widens every month

OUTRIGGER OPS™ deploys a complete agent stack across your business — closing the gap before competitors make it permanent.

What OUTRIGGER Builds For You

Systems that run. Proof you can show.

OUTRIGGER builds and connects the operational systems your business needs to grow, scale, and sell — automated marketing and lead generation, real-time cash flow visibility via OUTRIGGER BALANCE™, validated business valuation via OUTRIGGER HORIZON™, and documented operations that run without you in every decision.

  • Marketing & Lead GenerationAutomated outbound sequences, CRM management, lead scoring, and pipeline nurture — running continuously without a marketing team — without a marketing team.
  • Revenue Operations & PipelinePipeline tracked, stalled deals flagged, revenue forecast updated weekly. Your board gets live KPI dashboards — not manually compiled reports.
  • Cash Flow & Financial VisibilityOUTRIGGER BALANCE™ gives you 90-day cash flow visibility, scenario modeling, and runway alerts. You set it up separately and own the account throughout and after any OUTRIGGER engagement.
  • Operational AutomationEvery high-volume manual workflow identified and automated. Your team stops doing $20-per-hour work and starts focusing on what actually moves the business.
  • Valuation TrackingOUTRIGGER HORIZON™ tracks your valuation quarterly against live market benchmarks. Set it up when you are ready and keep it running long after any program ends.
70%
Of small businesses never find a buyer when listed for sale — not because they are unprofitable, but because they are not transferable IBBA Market Pulse Report
30%
Of current work hours are automatable today using existing AI technology — businesses not deploying agents are losing ground every month McKinsey Global Institute, 2024
Of a CEO’s working hours are spent in meetings — more than any other single activity, according to researchers at Harvard Business School and London School of Economics Harvard Business School & London School of Economics
66%
Of family-owned businesses have no documented succession plan — meaning the business value walks out the door when the owner does PwC US Family Business Survey, 2023
The OUTRIGGER Vision

A sailboat race taught us everything about building a business.

OUTRIGGER was born from the water. The name, the products, and the methodology all trace back to one insight from competitive sailing: a vessel does not win a race because it is the fastest. It wins because every part works together — hull, ama, sail, and crew — each doing its job at the right moment, in the right sequence.

A sailboat race has distinct phases. So does building a business worth owning, scaling, or selling. The crew that wins is not the one working hardest — it is the one with the right systems, the right coordination, and the clarity to know exactly where they are on the course at every moment.

OUTRIGGER maps that race to your business. Four tools. Four roles. One course.

01
Hull — Kino / Ka'ele

The Foundation Must Be Sound

Before any race starts, the hull is inspected. Every system checked. Nothing left to chance. Businesses that grow and sell at premium multiples have the same thing in common — their operations are documented, connected, and running without the owner in every decision. OUTRIGGER OPS™ builds that foundation.

OUTRIGGER OPS™
02
Ama — The Stabilizer

Stability Allows Speed

A racing crew that does not know its fuel level cannot push the vessel. A business owner who cannot see their cash position 90 days ahead cannot make confident decisions. OUTRIGGER BALANCE™ is the ama — the stabilizing float that keeps you upright when conditions change and gives you the visibility to accelerate without fear.

OUTRIGGER BALANCE™
03
Mast & Sail — Kia & La

Know the Horizon Before You Reach It

The best navigators do not react to what is in front of them. They read the water, the wind, and the horizon ahead. OUTRIGGER HORIZON™ gives you that forward view — AI-powered business valuation benchmarked against live market data, so you know exactly what your business is worth today and what moves the number before you go to market.

OUTRIGGER HORIZON™
04
ʻIako & Navigator — Connection & Course

The Crew That Calls the Race

In a race, the navigator calls the course, the crew executes, and the ʻiako holds everything together. OUTRIGGER NAVIGATOR™ connects every system in your business, deploys the operating infrastructure, and steers you toward the finish line — whether that is your next funding round, a market-leading growth position, or the exit you have spent years building toward.

OUTRIGGER NAVIGATOR™

Every OUTRIGGER product is a separate tool you own independently — your account, your data, your access. Use one. Use all four. Keep them long after any engagement ends. The outrigger stays with the vessel.

Your Next Move

Know where you stand.
Build what is missing.

Start with a free readiness score and see exactly what is keeping your business from the growth, scale, or exit you are building toward — in 5 minutes, no call required, instant results.

Free scores · Instant results · No call required · OUTRIGGER OPS™ from $299/month