Creating a 3-5 Year Strategic Plan That Can Help Make Your Company Buyer Attractive

There is a version of strategic planning that most privately held companies do: a few days offsite, a lot of Post-it notes, a slide deck that gets reviewed once and then lives in a shared drive. That process has value. But it is not what we are talking about here.

When your company has crossed $10M in revenue and you are thinking about your next decade — whether that includes a sale, a recapitalization, an ESOP, or simply building lasting enterprise value — you need a strategic plan that does something more specific. You need a plan that simultaneously guides your operating decisions and helps make your company legible, attractive, and credible to outside capital.

A well-constructed 3-5 year strategic plan serves as both your internal compass and your external proof of concept. It tells a buyer, a banker, or a private equity partner that you know exactly where this business is going and why it will get there. This article is about building that kind of plan.

 

What Buyers and Capital Partners Actually Look For

Before you can build a buyer-attractive plan, you need to understand how outside parties evaluate a business at your stage. The questions a strategic buyer or private equity firm is really asking are remarkably consistent:

Is this growth repeatable? Not just “did you grow?” but “can you explain why you grew and replicate it?” Buyers want to see a documented growth engine, not a charismatic founder who happens to have great customer relationships.

Is the leadership team capable of executing without the current owner? This is the key-person risk question. If the plan says “we will grow revenue by 40% over five years” but the whole plan depends on you personally, it is not worth much to a buyer.

Are there identifiable risks — and has management thought about them honestly? Buyers discount value for uncertainty. A plan that acknowledges concentration risks, competitive threats, or regulatory exposure and addresses them directly is a more credible document than one that ignores them.

Is the financial model realistic and tied to operating assumptions? Revenue projections that are not connected to specific customer segments, sales capacity, or market dynamics are not plans — they are wishes. Buyers model scenarios, and they need inputs.

 

The Five Components of a Buyer-Attractive Strategic Plan

A plan that will hold up to outside scrutiny needs to address five areas:

  1. Market Position and Competitive Differentiation
  2. Start with an honest assessment of where you compete and why you win. 
  3. What is the size of your addressable market? 
  4. Where are you gaining share and where are you losing it? 
  5. What are the one or two genuine advantages you have over alternatives — and are those advantages durable or eroding?

Owners often struggle here because the real answer is “we win because of relationships” or “we win because we have been doing this longer.” Those can be legitimate competitive advantages, but only if they are codified in something that outlasts the current owner — a culture, a process, a team, a customer success system.

 

Growth Engine: Where New Revenue Comes From

A buyer-attractive strategic plan must have an explicit theory about where new revenue will come from over the planning horizon. This means being specific about:

  • Which customer segments you are targeting and why they are underserved
  • What your sales capacity and sales model look like, and how they will scale
  • Which adjacent markets or geographies are realistic extensions versus wishful thinking
  • What the unit economics of new customer acquisition look like

Growth plans that simply extrapolate the last three years without explaining the mechanism for that growth are not persuasive. A plan that says “we will grow 12% per year by adding two salespeople per year in these three markets, targeting this specific buyer profile, with a sales cycle of this duration” is a completely different document.

 

Operational Scalability and Infrastructure

For companies in the $10M-$300M range, one of the most common buyer concerns is whether the infrastructure can support the growth the plan promises. Can your technology, your management team, your supply chain, and your back-office systems handle 50% more revenue without proportional increases in headcount?

This section of the plan should address: what investments in systems, processes, and people you are making and why, where the current bottlenecks are and how you are addressing them, and what your operating margins look like as you scale. Companies that have done the work to professionalize operations often commands premium multiples because buyers do not have to price in the risk of rebuilding from scratch.

A strategic plan that acknowledges real constraints and explains how you will address them is always more credible than one that promises growth without friction.

 

Financial Projections and Key Assumptions

The financial model is not just a spreadsheet. It is the translation of every strategic claim you just made into numbers with specific assumptions behind them. For a buyer-attractive plan, your financials should include:

  • A three to five year income statement projection with clear revenue build-up by segment or product line
  • EBITDA margins at each stage of the plan, with an explanation of margin expansion assumptions
  • A capital expenditure plan that reflects the infrastructure investments you described
  • A balance sheet view that shows how debt, equity, and cash flow evolve over the planning period
  • Key operating metrics that you track and that tell the story of business health

The goal is not to predict the future perfectly. The goal is to show that you think about the business with enough rigor and depth that outside capital can form an educated view.

 

Risk Register and Mitigation Plans

The fifth and often most overlooked component of a buyer-attractive strategic plan is a candid risk register. This is a short but honest list of the key risks to the plan — key-person dependencies, customer concentration, regulatory changes, competitive threats, supply chain vulnerabilities — and your active plan to manage each risk over the planning horizon.

This section demonstrates maturity. Many owner-operators feel that naming risks invites problems or shows weakness. In fact, the opposite is true. A buyer who is going to spend months doing due diligence will find the risks anyway. An owner who identified them proactively and is actively managing them shows sophistication and confidence.

 

Making the Plan an Operating Document

A strategic plan that sits in a drawer has no value. The operational cadence matters as much as the document itself.

  • Translate the three to five year plan into an annual operating plan with quarterly milestones and clear owners for each initiative
  • Review strategic progress at least quarterly with your leadership team, not just financial performance
  • Update the plan annually — not from scratch, but with fresh assumptions and a full review of what changed
  • Make the plan visible to your key leaders so they can align their teams and individual decisions with the strategic direction

This cadence serves you internally and sends a strong signal to outside parties. When a buyer sees a company that has been executing consistently against a documented strategic plan, they see a business that can continue to perform after the transition.

 

Ready to Take the Next Step?

If your company is between $10M and $300M in revenue and you want to build a strategic plan that serves as both your operating roadmap and a compelling narrative for capital partners or future buyers, Vertex Planning Partners can help you structure the conversation. Reach out to explore what that process looks like for your business.

 

 

This material is for informational purposes only and does not constitute investment, tax, or legal advice. Vertex Partners is a registered investment advisor. Consult with qualified professionals before making financial decisions.

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Peter M. Babilla, CFP®, CRPS®

PARTNER

Peter Babilla brings 40 years of experience in investment management and fiduciary* financial consulting to Vertex Planning Partners, LLC.

Pete graduated from Indiana University in Bloomington, Indiana with a Bachelor’s of Science in Finance.

He began his career in 1983 with a focus on institutional fixed-income portfolio management, primarily working with community banks. After a decade serving institutional clients, Pete shifted his focus to working with individuals, families and business owners, providing guidance and education in all areas of Wealth Management.  Among his areas of focus are accumulation and retirement planning, investment management, risk management, and estate and wealth transfer.

Pete’s planning philosophy allows him to create a personalized program for clients, based on their own unique goals and circumstances.  The extensive investment and planning platform offered by Vertex enables him to create a highly customized program, tailored to each individual client.

Pete and his wife Suzanne have two children, and have resided in Wheaton, Illinois for the past 30 years.  He enjoys golf, reading, and traveling with his family.  Pete gives back as a past Board Member of the Epilepsy Foundation of Greater Chicago, where his focus is on improving the lives of those living with epilepsy.

Pete works as fiduciary for his clients and holds the CERTIFIED FIANANCIAL PLANNER™ (CFP®) designation and the Chartered Retirement Plan Specialist (CRPS®) designation.

Justin J. D'Agostino, CPWA®, CFP® , TPCP®, ChFC®, CRPC®

PARTNER

Justin D’Agostino is a Partner and Private Wealth Advisor at Vertex Planning Partners, advising business owners, executives, and high-net-worth families on investments, financial planning, tax and succession planning.

He coordinates the full advisory team around each client to keep tax, investment, and planning decisions moving in the same direction. Justin’s approach centers on rigorous, data-driven analysis — modeling outcomes across planning scenarios so clients can make decisions with clarity.

With over a decade of experience, Justin’s work focuses on:

  • Investment & Portfolio Strategy
  • Tax-Efficient Planning
  • Equity Compensation & Concentrated Stock
  • Retirement & Distribution Planning
  • Estate & Succession Planning

Justin attended Hillsdale College, where he earned his BA in Accounting and Financial Management. He is an avid sports fan and enjoys spending weekends with his family.

Designations:

  • Certified Private Wealth Advisor®
  • CERTIFIED FINANCIAL PLANNER™ Professional
  • Tax Planning Certified Professional®
  • Chartered Financial Consultant®
  • Chartered Retirement Planning Counselor™

 

Justin does not provide tax or legal advice. He works alongside each client’s CPA and attorney on those matters.

CRPC conferred by College for Financial Planning.

Scott A. Sandee CFP®, CIMA®, CPWA®, CEPA

MANAGING PARTNER

Scott Sandee brings over 20 years of experience to his role as Managing Partner of Vertex Planning Partners, leading the firm’s efforts to assist middle-market business owners and eight and nine-figure families in comprehensive planning. We enable clients to achieve their financial goals by tailoring solutions to their unique aspirations and situations. Leveraging his experience in sophisticated investment techniques and financial strategies with privately held family businesses, supported by extensive post-graduate education focused on exit planning, wealth management, estate planning, investment analysis, insurance planning, risk management, and tax optimization, he:

  • Assist owners in preparing for and executing a successful transition.
  • Develop financial strategies to maximize sales proceeds and reduce future taxes.
  • Listen carefully and create personalized solutions that reflect each client’s unique hopes, goals, and concerns.
  • Explain complex and technical concepts with clarity and simplicity.

 

Scott guides successful entrepreneurs and wealthy families through the transfer of ownership of their privately held companies.

Designations: Certified Financial Planner® Certified Private Wealth Advisor® Certified Investment Management Analyst® Certified Exit Planning Advisor Certified Merger & Acquisition Advisor

Julie Hupp CFP®, MBA

PARTNER

Julie Hupp, CERTIFIED FINANCIAL PLANNER™ professional, has worked in the accounting and corporate finance field since 1987. She began her career as a CPA with Deloitte & Touche, specializing in the financial needs of small businesses. Then spent the next 13 years in corporate financial planning and business development at Baxter and TAP Pharmaceuticals. Recognizing her passion for personal financial planning, Julie started her business in 2006 where she focuses on comprehensive financial planning strategies and implementation.

Julie graduated from University of Illinois with a BS in Accountancy. She received her Master’s in Management with a concentration in Finance from Northwestern University’s Kellogg School of Management in 1994.

Outside the office, Julie is the co-founder of the 12 Oaks Foundation, which has merged with Cal’s Angels, and is a former Board member. Julie enjoys cooking, reading, running, triathlons and doing almost anything outdoors. A great weekend is spending time with her husband and two adult kids boating at their lake house in Wisconsin.

Steven P. Franzen, CPA, PFS, CGMA

MANAGING PARTNER

Steven P. Franzen, CPA, PFS, CGMA is a public accountant and consultant with more than 23 years of experience helping individuals and businesses reduce their tax liability.  He began his career under the guidance of Patrick M. De Sio, CPA, CGMA and in 1996 became Mr. De Sio’s partner in De Sio, Franzen & Associates, Ltd. Steve’s expertise include entity design, complex tax strategies and multigenerational wealth transfer.  As Managing Partner, Steve conducts his practice under the philosophy that the client’s investment in their CPA should yield a return on that investment – most of the time that return is realized when working with clients on planning for their future. In an effort to increase the planning capabilities of the firm,  Steve formed Vertex Accounting Partners, LLC to ensure their guiding philosophy will continue well into the future.

Steve is a certified public accountant and has earned the professional designations of Personal Financial Specialist and Chartered Global Management Accountant.  He is a member of the American Institute of Certified Public Accountants and the Illinois CPA Society.  Steve earned a B.S. degree in accounting from Millikin University.  He and his wife Kristie live in Sugar Grove, IL with their three children.

Gregory P. Benner, MST, CPWA®, CFP®, CLU®, ChFC®, AIF®, RMA®

MANAGING PARTNER

Greg Benner advises high-net-worth and ultra-high-net-worth business owners, individuals and families on advanced tax, risk management, retirement, estate planning, and wealth strategies.  

As a co-founder of Vertex Planning Partners, he works closely with clients, families, and their professional advisors—CPAs, attorneys, and business stakeholders—to implement thoughtful, durable planning strategies. His approach prioritizes clarity, coordination, and disciplined execution.

For twenty-four years, Greg’s work has focused on designing and coordinating multi-factor, integrated plans involving:

  • Tax Efficiency
  • Wealth Transfer Structures
  • Retirement Planning
  • Investment Strategy, and
  • Long-Term Financial Architecture

 

Drawing from his own experience as a founder, business and real estate investor, and multi-generational family business member, he understands some of the challenges that can arise for business owners as they consider an exit. Multi-disciplinary, intentional planning with stakeholder communication creates structure, mitigates risk, addresses tax implications, and preempts issues that can arise.

Greg holds a Master of Science in Taxation, a graduate program that deepened his technical training in federal income taxation, partnership and corporate taxation, estate and gift tax, and tax procedure. This academic work enhances his ability to help families and business owners navigate complex tax environments and align their financial and estate-planning objectives across generations.

Designations:

  • Certified Private Wealth Advisor®
  • Certified Financial Planner®
  • Chartered Financial Consultant®
  • Chartered Life Underwriter®
  • Accredited Investment Fiduciary®
  • Retirement Management Advisor®

 

Licenses:

  • Series 65 registration held with Vertex Planning Partners, LLC
    Illinois, Ohio, Wisconsin & Louisiana Life & Health Insurance License

 

Greg is deeply committed to lifelong learning and continuous professional development in the areas of tax, estate planning, and private-wealth strategy.

Michael D. Bellis, CFP®, CLU®

MANAGING PARTNER

Michael D. Bellis, CFP®, CLU® began his career as a financial planning professional in 1994. His practice is centered on holistic financial planning, astute risk management strategies and empirical, research-driven portfolio construction. He began his career in partnership with his father under the name Bellis & Associates. Together, their practice and reputation for excellence dates back more than 40 years and includes multiple generations of the same families. After his father’s retirement several years ago, Mike continued to build a client-centric, consultative practice before forming Vertex.

Mike holds the CERTIFIED FINANCIAL PLANNER™ certification and is also a Chartered Life Underwriter. He has been an active member of both the Society of Financial Services Professionals and the National Association of Insurance and Financial Advisors. He earned a B.S. in Business & Marketing from Illinois State University. Mike is a lifelong resident of Naperville, Illinois. He and his wife Tanja have three children.