How to Get Your Company Acquired: Relationship-Led Outcomes

Dawn Lepore, Former CIO of Charles Schwab and Former CEO of drugstore.com

Dawn Lepore is an advisory board member at Lead Edge Capital and a seasoned executive who led drugstore.com through its acquisition by Walgreens. She previously held senior leadership roles at Charles Schwab, including Vice Chairman of Technology, Operations, and Strategy, and has served on the boards of major public companies across technology, retail, and media.

What Founders Should Know About How to Get Your Company Acquired

• Acquisition starts with strategy. Founders must weigh the risks and rewards of remaining independent versus being acquired.
• Values alignment matters. Successful outcomes depend on complementary goals between buyer and seller.
• Relationships come first. Early conversations should focus on trust-building, not transactions.
• Information sharing requires judgment. Transparency must be balanced with caution.
• Advisors reduce risk. Experienced guidance helps founders navigate competing agendas.
• Leadership requires selflessness. CEOs must prioritize the company’s long-term outcome over personal preference.

What to Know Before Engaging Potential Acquirers

How should founders think about being acquired?

Founders must approach acquisition decisions with an open mind. Lepore emphasizes the importance of understanding long-term strategy and remaining flexible as opportunities emerge. Remaining dogmatic about independence can limit options, while thoughtful openness preserves leverage.

How should early conversations with acquirers begin?

Initial discussions should be relationship-driven. Founders should invest time in informal conversations, learning how the other party thinks, what motivates them, and how they evaluate success. Sharing enough information to build interest is important, but naïveté can create risk.

Why are trusted advisors critical?

Advisors who have navigated acquisitions before can help founders interpret signals, identify misalignment, and manage the many agendas involved. Their perspective is especially valuable when emotions or pressure influence decision-making.

What role does the CEO play in closing a deal?

The CEO’s role is often selfless. Lepore describes situations where leaders accepted less favorable personal terms to secure the best outcome for the company. This mindset can be decisive in completing a deal that benefits employees and shareholders.

How can founders increase the odds of a successful outcome?

Strong relationships with the buyer’s internal champion are essential. Founders should understand who is advocating for the deal internally, clarify success metrics early, and use their network to assess how the deal is being perceived behind the scenes.

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About Dawn Lepore

Dawn Lepore is a former CEO of drugstore.com and former CIO of Charles Schwab. She has led companies through acquisition, served on numerous public boards, and advises growth-stage leaders on strategy, governance, and exit readiness.

How to Get Your Company Acquired FAQs for Founders

How do founders know when acquisition is the right path?

By evaluating long-term strategy, market conditions, and the trade-offs between independence and partnership.

Should founders wait for acquirers to approach them?

No. Building relationships early creates optionality and improves outcomes.

How much information should be shared with potential buyers?

Enough to sustain interest, but only with safeguards and trusted guidance.

Why are internal champions important?

They advocate for the deal internally and influence decision-makers.

What increases deal success?

Preparation, aligned values, trusted advisors, and disciplined leadership.