Retirement Exit Planning for Business Owners | OUTRIGGER ADVISORY GROUP™
Retirement Exit Planning

One day, you will walk out
for the last time.

You spent decades building this. The team, the customers, the reputation, all of it carries your fingerprints. Now you are thinking about what comes next. Whether retirement is two years away or ten, the planning starts the same way: knowing exactly where your business stands today.

Take the Exit Readiness Score™ → Free · 23 questions · Instant results · No call required

The hardest day in a business owner’s life is not the day they start. It is the day they walk away.

For most owners approaching retirement, the question is not whether to step back. It is when, how, and whether the business will be ready when you are. The good news: that question has a clear answer. The Exit Readiness Score™ gives it to you in 12 minutes, with no sales call and no commitment.

What Owners at Your Stage Are Really Asking

The questions nobody puts on a spreadsheet.

The financial questions are real. So are the ones underneath them. Most retirement-planning conversations skip past these. We do not.

If I sell, what do I do on Monday morning?

My kids do not want the business. Now what?

Who am I, if I am not the owner of this company?

Will the team be taken care of after I leave?

Did I wait too long to start planning this?

What will the legacy actually look like in ten years?

The Exit Readiness Score™ addresses the operational and financial side — the part that determines what your business is actually worth and what a buyer will pay. The other questions matter just as much. We address those in the conversation that follows, when you are ready.

What the Exit Readiness Score Reveals

Eight dimensions. One score. Clarity on where you stand.

01
Financial Readiness

Clean books, audited financials, three years of trends a buyer can verify.

02
Owner Dependence

How much of the business actually runs without you in the room.

03
Customer Concentration

Is the revenue diversified, or does one client carry too much weight?

04
Recurring Revenue

The percentage of revenue that arrives predictably every month.

05
Operating Systems

Documented processes that let a new owner pick up where you leave off.

06
Team & Leadership

A team that runs without you, with someone trained to lead going forward.

07
Market Position

Your competitive advantage and how defensible it is to the next owner.

08
Transition Timeline

How quickly the business can be ready, given where it stands today.

Twelve minutes. No sales call. No credit card. Your score arrives in your inbox, with a personalized breakdown of where you are strong and where to focus first.

Take the Exit Readiness Score™ →
The Timeline Most Owners Wish They Had Known

A business is not ready to sell the day you decide to sell.

Here is what the actual path looks like when an owner approaches it with a plan.

Years 5 to 3 01

Build the business that does not need you

This is where the multiple is made. Document processes. Train a leadership team. Reduce customer concentration. Clean up the financials. Owners who do this work get 3-5x higher valuations than owners who skip it.

Years 3 to 1 02

Position the business for the right buyer

Market positioning, financial packaging, key employee retention plans. This is when the business goes from a job into an asset that a buyer recognizes. The right preparation determines who shows up at the table.

Year 1 to Close 03

The exit itself

Buyer outreach, due diligence, negotiation, close. With the right preparation, this stage is methodical. Without it, it is where good businesses get undervalued or walked away from entirely.

After 04

Life after the business

The transition you have actually been planning for. What you do on Monday morning. What the legacy looks like. Owners who plan for this stage find the transition rewarding rather than disorienting.

If you are reading this with less than three years until you want to walk away, you are not too late. But the sequence matters. The Exit Readiness Score™ tells you which stage you are actually in and what to focus on first.
Who You Are Working With

A broker who understands
both sides of the table.

Amber Pember, MBA, has spent her career on the operational side of growing and selling businesses. As an eXp Commercial business broker, she represents owners through their exit. As the founder of OUTRIGGER ADVISORY GROUP™, she also helps owners prepare for that exit years in advance.

The Exit Readiness Score™ is the front door. If your score reveals you are ready to go to market, we have the brokerage relationships to take you there. If your score reveals you need preparation first, we have the tools and the team to do that work.

Either way, the conversation starts with knowing where you stand today.

Amber Pember, MBA
Founder, OUTRIGGER ADVISORY GROUP™ · Business Broker, eXp Commercial
What the Score Includes
  • Your overall Exit Readiness Score out of 100
  • Dimension-level breakdown across all 8 areas
  • The 3 highest-impact priorities for your specific situation
  • An estimated valuation range based on your readiness profile
  • Timeline assessment — how long preparation will take
  • A recommended next step, with no obligation to take it
Your Next Twelve Minutes

The hardest part of planning your exit
is starting.

Most owners delay this conversation by three or four years longer than they should. The ones who do not are the ones who walk away on their own terms. Take the assessment. See where you stand. Decide what to do with that information when you are ready.

Take the Exit Readiness Score™ → Free · 23 questions · Instant results · No sales call required