Playbook Library

45 Playbooks That Turn Weaknesses into Value

Each playbook is an interactive, guided workflow. Not a PDF. Not a checklist. A step-by-step process that produces real deliverables and moves your Exit Score.

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45
Interactive playbooks
6
Categories
4
Free forever
👤

Personal

4 playbooks · Prepare yourself for the transition
Financial Independence Calculator
Free
Calculate your personal financial independence number. See the gap between projected exit proceeds and what you need for your desired lifestyle.
~45 min6 steps
Post-Exit Identity Planning
Growth
Explore what comes after the exit. Define your next chapter, assess readiness for the identity shift, and build a personal transition plan.
~30 min5 steps
Family Alignment Workshop
Growth
Align family members on exit timing, expectations, and post-exit roles. Guided conversation framework that prevents surprises.
~60 min4 steps
Deal Fatigue Prevention Plan
Growth
Prepare for the emotional marathon of a deal process. Set boundaries, build support systems, and create decision frameworks for high-stress moments.
~25 min5 steps
💰

Financial

9 playbooks · Clean up, optimize, and demonstrate financial strength
Tax Strategy & Structure Review
Growth
Review your entity structure, identify tax optimization opportunities, and prepare for the tax implications of an exit transaction.
~60 min8 steps
Financial Statement Cleanup
Growth
Audit your financial statements for buyer readiness. Identify personal expenses, inconsistencies, and presentation issues that raise red flags.
~90 min7 steps
EBITDA Normalization
Free
Identify and document add-backs that increase your normalized EBITDA. Owner compensation, one-time expenses, and discretionary spending.
~45 min6 steps
Revenue Quality Analysis
Growth
Assess recurring vs. one-time revenue, contract strength, retention rates, and revenue predictability. Buyers pay premiums for quality revenue.
~45 min6 steps
Working Capital Optimization
Growth
Analyze your working capital cycle. Identify opportunities to improve cash conversion and reduce the working capital adjustment in a deal.
~40 min5 steps
Financial Projections Builder
Growth
Build defensible 3-year financial projections. Bottom-up methodology that buyers and their advisors can validate.
~75 min8 steps
Margin Improvement Roadmap
Growth
Identify and prioritize margin improvement opportunities. Every point of margin expands your valuation multiple.
~50 min7 steps
Pricing Power Assessment
Growth
Evaluate your pricing strategy and competitive position. Demonstrate pricing power that buyers value in acquisition targets.
~35 min5 steps
Cost Structure Analysis
Growth
Map fixed vs. variable costs, identify operational leverage, and highlight cost synergies a buyer could realize.
~40 min5 steps
⚙

Operational

8 playbooks · Build a business that runs without you
Owner Dependency Reduction
Free
Map every function you perform and build a delegation plan. The single biggest factor in transferability scoring.
~60 min8 steps
Management Team Strength Assessment
Growth
Evaluate your leadership team against buyer expectations. Identify gaps and build a development plan for key leaders.
~45 min6 steps
Key Employee Retention Plan
Growth
Design retention mechanisms for critical employees. Stay bonuses, non-competes, equity plans, and transition agreements.
~50 min7 steps
SOP Documentation Program
Growth
Create a standard operating procedure library for critical business processes. Makes the business operable by anyone, not just you.
~90 min8 steps
Technology & Systems Audit
Growth
Inventory your technology stack, assess technical debt, and identify systems that need upgrading before a transition.
~45 min6 steps
Vendor & Supply Chain Resilience
Growth
Assess supplier concentration, contract terms, and backup options. Single-source dependencies are red flags in due diligence.
~35 min5 steps
Quality Management Review
Growth
Document quality standards, track metrics, and demonstrate consistent delivery. Quality systems signal operational maturity.
~40 min5 steps
Scalability Assessment
Growth
Evaluate whether your business can grow 2-3x without proportional cost increases. Buyers pay premiums for scalable operations.
~35 min5 steps
⚖

Legal

8 playbooks · Eliminate legal risks before due diligence
Corporate Housekeeping Audit
Growth
Review corporate governance, minutes, filings, and records. Messy corporate housekeeping kills deals and reduces multiples.
~75 min9 steps
Intellectual Property Audit
Growth
Inventory and protect your IP: trademarks, patents, trade secrets, proprietary processes. Unprotected IP is a deal risk.
~60 min7 steps
Contract & Agreement Review
Growth
Audit customer contracts, vendor agreements, and partnership terms. Identify change-of-control clauses and assignability issues.
~60 min7 steps
Employment Compliance Check
Growth
Review employment agreements, contractor classifications, benefits compliance, and potential exposure areas.
~50 min6 steps
Regulatory Compliance Audit
Growth
Map industry-specific regulatory requirements and verify compliance. Non-compliance discovered in due diligence is a deal breaker.
~45 min6 steps
Data Privacy & Security Review
Growth
Assess data handling practices, privacy policy compliance, and cybersecurity posture. Critical for any business handling customer data.
~40 min6 steps
Involuntary Exit Preparedness
Growth
Plan for the unplanned. Key-person insurance, succession protocols, and emergency operating procedures.
~35 min5 steps
Partner & Shareholder Alignment
Growth
Review operating agreements, buy-sell provisions, and shareholder rights. Misaligned partners derail deals.
~45 min6 steps
📈

Market & Growth

5 playbooks · Demonstrate market position and growth potential
Customer Concentration Analysis
Free
Map revenue concentration, calculate your HHI index, and build a diversification strategy. Top customer representing >20% of revenue is a red flag.
~45 min7 steps
Value Driver Acceleration
Growth
Identify and amplify the 3-5 value drivers that have the most impact on your multiple. Focused execution that moves the needle fastest.
~50 min6 steps
Strategic Growth Plan
Growth
Build a credible growth narrative with supporting data. Buyers pay for demonstrated growth momentum and addressable market opportunity.
~60 min7 steps
Brand & Reputation Strengthening
Growth
Assess brand strength, online reputation, and market perception. Build a plan to strengthen positioning before going to market.
~40 min5 steps
Market Timing Analysis
Growth
Evaluate industry cycle position, M&A market conditions, and optimal timing for your exit. Timing can mean a 2x difference in multiples.
~35 min5 steps
🤝

Deal Prep

10 playbooks · Run the deal process like a professional · Deal Room plan
Valuation Benchmarking
Deal Room
Compare your valuation against industry benchmarks, recent comparable transactions, and public company multiples.
~45 min6 steps
Deal Team Assembly
Deal Room
Build your advisory team: investment banker, M&A attorney, tax advisor, wealth manager. Evaluation criteria and interview guides.
~40 min5 steps
Buyer Mapping & Targeting
Deal Room
Identify and categorize potential buyers: strategic acquirers, PE firms, family offices, and individuals. Build your target list.
~50 min7 steps
CIM Preparation
Deal Room
Build your Confidential Information Memorandum. The document that sells your business. Guided section-by-section creation.
~120 min12 steps
Data Room Preparation
Deal Room
Organize and populate your virtual data room. Checklist of every document buyers expect, organized by category.
~90 min10 steps
Deal Structure Options
Deal Room
Understand and evaluate deal structures: asset vs. stock sale, earnouts, seller financing, rollover equity. Know what to expect.
~45 min6 steps
Negotiation Preparation
Deal Room
Develop your negotiation strategy: walk-away price, priority terms, concession hierarchy, and BATNA analysis.
~50 min7 steps
Transition Planning
Deal Room
Plan the post-close transition. Knowledge transfer, customer introductions, team retention, and your earn-out performance plan.
~60 min8 steps
Due Diligence Preparation
Deal Room
Prepare for buyer due diligence before it starts. Anticipate questions, prepare answers, and organize evidence.
~75 min9 steps
LOI & Term Sheet Review
Deal Room
Evaluate and negotiate Letters of Intent. Guided framework for assessing terms, identifying red flags, and comparing multiple offers.
~40 min6 steps
How Playbooks Work

Not PDFs. Not Checklists. Interactive Guided Workflows.

Each playbook walks you through a structured process, asks the right questions, and produces real deliverables.

1

Guided Steps

Interactive questions and analysis tools walk you through each topic. Your AI Coach provides personalized guidance at every step.

2

Real Deliverables

Every playbook produces artifacts: analyses, checklists, plans, and documents you keep. No theoretical exercises.

3

Score Impact

Completing a playbook feeds data back into your valuation engine. Your Exit Score updates in real time as you address gaps.

Access by Plan

Start Free. Unlock as You Grow.

Foundation

4
playbooks included
  • Financial Independence Calculator
  • EBITDA Normalization
  • Owner Dependency Reduction
  • Customer Concentration Analysis
Free forever

Growth

35+
playbooks included
  • All Foundation playbooks
  • All Personal playbooks
  • All Financial playbooks
  • All Operational playbooks
  • All Legal playbooks
  • All Market & Growth playbooks
  • AI Coach guidance throughout
$99/mo (annual)

Deal Room

45
all playbooks
  • All Growth playbooks
  • 10 Deal Prep playbooks
  • Virtual data room
  • Deal pipeline management
  • Offer comparison tools
$249/mo (annual)

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The assessment identifies your specific gaps, then recommends the playbooks with the highest dollar impact on your valuation.

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Playbook Library - Exit OSx | Exit OSx