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Hiring a Wind-Down Expert: Five Essential Factors

Taylor received a call from her board, “We’ve got bad news. You’re going to need to shut down your startup”

Her heart sank, and her stomach tied in knots. She knew this was coming but hoped she had a few months left.

“We’ve got a couple of numbers for you to call. Pick a wind-down expert in the next few weeks, get rid of that debt, and we need to find a buyer fast.”

Taylor froze. Hire a wind-down expert? She didn’t even know where to begin.

Wind-Down Expert can pinpoint areas of wastage through meticulous financial analysis, identify underutilized assets, and strategically manage company resources. By having a forward-looking forecast, the company can strategically time asset sales, ensuring they fetch maximum value. Proper financial management, guided by analysis and forecasting, directly correlates to lowered obligations and maximized asset values.

In the critical moments when a company is considering winding down its operations, the expertise of a professional experienced in navigating such complexities can be invaluable. A Wind Down Expert, often synonymous with Chief Restructuring Officer (CRO)‘, provides seasoned guidance throughout this challenging process. Their role differs significantly from that of a Chief Financial Officer (CFO), as they specialize in financial modeling, growth, and fundraising and may not have the critical skills needed to wind-down a startup.

Five Essential Factors

1. Experience in Business Restructuring

The intricate maze of business restructuring requires not just knowledge but genuine experience. Companies are living entities, and restructuring them often necessitates making difficult decisions rapidly. An expert with hands-on experience can efficiently identify problem areas and potential opportunities and navigate the company through financial challenges.

Wind Down Expert with a proven track record in business restructuring will already have tried and tested strategies to deploy. They will be adept at predicting potential pitfalls, ensuring fewer surprises. By leveraging their past experiences, they can help minimize losses, ensuring that the company remains compliant and maximizes its remaining assets, thereby increasing asset value and minimizing obligations.


  • Can you describe a situation where you successfully steered a company through a complex restructuring or wind-down scenario?
  • How did you handle stakeholder communications during the most challenging restructuring you’ve overseen?
  • How do you align restructuring strategies with the company’s long-term vision or objectives?

2. Industry-Specific Knowledge 

Each industry has unique challenges, regulations, competitors, and market dynamics. A generalist might miss out on nuances that can greatly impact the wind-down process.

Having a CRO with industry-specific knowledge means they can quickly and accurately gauge the market value of assets, relationships, and intellectual property. They’ll know what’s invaluable and expendable, ensuring that liquidation or sales efforts are targeted and effective. This focus can lead to higher realized asset values and better deals during negotiations, benefiting creditors and stakeholders.


  • How have your previous experiences prepared you for the unique challenges present in our industry?
  • Can you provide an example of a company you’ve helped restructure or wind down in our sector? What strategies did you deploy?
  • What would you identify as the most pressing challenge in our industry regarding winding down operations?

3. Stakeholder Negotiation Skills

Stakeholders, including creditors, employees, investors, and vendors, all have vested interests in the company. Managing and negotiating with these groups is pivotal to ensure smooth proceedings and favorable outcomes.

Effective negotiation can lead to substantial reductions in owed amounts, better settlement terms, and the prevention of potential litigation. A skilled CRO can foster stakeholder collaboration by building trust and ensuring open communication, leading to mutually beneficial agreements that protect the company’s interests, reduce obligations, and maintain asset value.


  • Describe when you had to negotiate terms with a challenging creditor. How did you ensure a win-win situation?
  • How do you prioritize stakeholder communication amid a wind-down?
  • Can you share an instance where stakeholder negotiations influenced the restructuring strategy and how you navigated it?

4. Legal and Compliance Acumen

The winding down of operations doesn’t just involve business decisions; it is laden with legal implications. There are legal pitfalls at every turn, whether it’s contracts, employee rights, or creditor obligations.

A CRO with solid legal and compliance knowledge will seamlessly work alongside legal teams, ensuring the company stays compliant and avoids potential legal entanglements. The company can avoid costly penalties, lawsuits, or unforeseen liabilities by preemptively addressing potential legal issues and ensuring adherence to all regulations. This proactive approach safeguards the company’s assets and reputation.


  • Can you describe a situation where you had to work closely with legal teams during a restructuring process? What were the challenges, and how did you overcome them?
  • How do you fully comply with regulations and laws during a wind-down process?
  • Tell us about when you encountered unexpected legal challenges during a wind-down and the steps you took to address them.

5. Financial Analysis and Forecasting

At its core, winding down is about numbers. Ensuring the company’s assets are correctly valued and liquidated at the right time is paramount. Additionally, forecasting the company’s financial trajectory during this period is vital to anticipate cash flow and meet obligations.


  • Describe a scenario where your financial forecasting significantly impacted the restructuring or wind-down process. What was the outcome?
  • How do you approach the valuation and liquidation of assets in a wind-down scenario?
  • Can you provide an example of a financial analysis that shifted the direction or approach of your wind-down strategy?

Other things to consider: 

When considering a Wind-Down Expert or CRO, it’s imperative to gauge their ability to think strategically while managing the intricate details involved. Focusing on these critical factors and associated questions, you’ll be well-equipped to make an informed decision.

  • Describe a situation where you had to make a difficult decision quickly. How did you handle it, and what was the outcome?
  • How do you prioritize tasks when faced with multiple urgent demands?
  • Can you provide an example of a complex project or process you managed using a checklist or a similar tool? How did you ensure all items were addressed?
  • Describe a time when attention to detail was crucial in your role. How did you ensure that all details were covered?

Strategic Vision:

  • Tell me about when you had to adjust or change your strategy mid-course due to unforeseen challenges. How did you handle it, and what did you learn?
  • Describe a situation where you had to think several steps ahead to navigate a complex problem.

Financial Acumen:

  • Share an example of how you used financial data or insights to make a strategic business decision.
  • How do you assess the financial health of a company facing challenges? What key metrics do you prioritize?

Strong Communication Skills:

  • Describe a situation where you had to communicate a difficult message to stakeholders. How did you approach it?
  • How do you inform all relevant parties during a challenging or rapidly changing situation?
  • Emotional Intelligence:
  • Describe a time when you had to manage a team or individual through a difficult period. How did you handle it and ensure the well-being of the person/team?
  • Share an example of when you received critical feedback. How did you respond, and how did it influence your actions moving forward?

Additional Questions:

  • In your experience, what are the key factors determining a successful wind-down process?
  • How do you handle situations where there are competing interests or priorities among stakeholders?

Considering the right exit strategy for your startup can be a complex decision. Let our Chief Restructuring Officers guide you through the intricacies of turnarounds, restructuring, bankruptcy, ABCs, and wind-downs. Receive a complimentary Wind-Down Playbook, offering you valuable insights into the most suitable wind-down approach for your VC-backed venture and a one-hour consult to determine the best next step for your startup.