What to Do 12, 24, and 36 Months Before a Sale
Most founders wait too long to prepare.
Not because they’re unaware—but because they’re focused on execution.
Revenue’s growing. Customers are happy. If a buyer called tomorrow, they could “pull it together.”
That’s the trap.
Because once a deal is in motion, it’s too late to fix what really matters.
Buyers don’t just evaluate your business. They evaluate how ready it is to be bought.
Why Timeline Matters
The best businesses don’t just operate well—they hold up under scrutiny.
And scrutiny shows up in diligence:
Financial accuracy
Customer concentration
Crew-level performance
Margin trends
Leadership depth
Founder reliance
Contract clarity
System maturity
If you’re addressing these after an LOI, you’ve already lost leverage.
What to Focus On: 36, 24, and 12 Months Out
Whether you plan to sell or just want the option to, here’s what to prioritize.
36 Months Out: Build the Foundation
This is where value is created—or capped.
Shift from Gut to System
Document core processes: quoting, job flow, collections, inventory, training
Identify founder-owned decisions and assign backups
Launch weekly reporting: margin, crew efficiency, return visits, escalations
Track Margin at the Field Level
Set gross margin targets by job type
Build visibility (manual or tech-enabled)
Train crews on how they affect profitability
Get Leadership in Place
Hire or elevate leads across ops, finance, scheduling, and customer service
Hand off one function per quarter
Track outcomes without daily involvement
Fix Structural Issues Early
Normalize the financials
Stop mixing personal and business expenses
Resolve 1099 vs. W2 misalignments
Move key contracts under the business entity
Clean the Cap Table
Close out handshake equity
Address silent investors
Align all documents
Outcome: You’re no longer essential to daily execution, and structural blockers are removed before they show up in diligence.
24 Months Out: Professionalize for Diligence
This is when buyers start taking notice.
Tune Financial Visibility
Close books monthly, accurately, and fast
Break out revenue by job type, crew, or region
Reconcile margins by line of business
Build Redundancy Around You
You no longer quote, schedule, or solve daily problems
Managers run the business; you review performance
If you step out for two weeks, nothing breaks
Tighten Legal and Admin
Store all contracts digitally
Ensure employment agreements are current
Audit licensing, insurance, and compliance
Clarify Customer Relationships
For key accounts: assign ownership, track engagement, define stickiness
Light CRM usage is enough—visibility matters more than complexity
Track Labor Productivity Weekly
Revenue per truck, jobs per day, gross margin per crew
Push accountability into the field, not just into ops leadership
Outcome: You’re not just growing—you’re operating in a way buyers can trust and validate.
12 Months Out: Signal Strength
Now is when buyers start forming first impressions.
Defend Margin
Eliminate underpricing and scope creep
Coach quoting team weekly
Tie increases to cost data, not gut feel
Lock in Growth Predictability
Demonstrate pipeline consistency
Ensure new revenue is sourced without you
Document how demand is generated—even if it’s simple
Clarify the Narrative
Know your three-year arc: what changed, what’s fixed, what’s scalable
Articulate your thesis: why someone would want to own this business
Tighten it into a one-pager before you need it
Strengthen the People Equation
Standardize compensation
Document how teams are hired, trained, and managed
Address underperformance proactively
Prepare the Data Room
Organize folders for finance, legal, ops, HR, and customer files
Assign internal ownership
Label and date everything
Outcome: The business doesn’t just operate cleanly—it presents as a high-confidence acquisition before it’s ever marketed.
Deal-Readiness Diagnostic
Answer honestly:
Could you step away for 30 days without performance dipping?
Do you know your gross margin by job type—and is it trending up?
Are all vendors, customers, and employees under contract?
Can you explain three years of financials in five minutes—with support?
Would a buyer see leadership beneath you—or only you?
If you answered “no” to more than one, the business isn’t ready to sell.
It’s ready to start preparing.
Final Thought
The best exits don’t happen because a business performs.
They happen because the business was prepared.
Buyers reward clean systems, clear leadership, and operational maturity—with better terms, less structure, and faster closes.
Whether you’re selling in 12 months or five years, preparation builds leverage.
The time to start is now.
For weekly playbooks on building leverage, preparing for exit, and operating with intent, subscribe to The Grey Brief.