Cindy Free is the Owner and CEO of HR Annie Consulting, a boutique HR consulting firm based in Portland, Oregon, serving companies across the United States. With nearly 16 years in business, Cindy has developed a niche in supporting scaling companies that are preparing for mergers, acquisitions, or eventual exits. She helps organizations reduce risk, strengthen leadership teams, and build HR infrastructure that increases company value.
HR Annie Consulting’s HR M&A support for investors, independent buyers, and sellers bridges the critical gap in traditional due diligence—the people side of the business—by offering pre-acquisition and seller assessments, transition roadmaps, and post-deal integration support.
Here’s a glimpse of what you’ll learn:
- [03:20] Why HR is often overlooked in M&A due diligence.
- [06:40] The three HR vantage points every business must address before exiting.
- [09:00] How compliance gaps can derail or devalue a transaction.
- [12:30] Why culture metrics like retention and engagement matter to buyers.
- [17:20] How building A++ leadership and repeatable systems increases valuation
In this episode:
When business owners prepare for an exit, they focus on revenue, financials, and inventory—but often overlook one of their most valuable assets: their people.
In this episode, Adi Klevit welcomes back Cindy Free to discuss why HR plays a critical role in mergers, acquisitions, and business exits. Cindy explains that while financial due diligence is standard practice, HR due diligence is frequently ignored. This oversight can expose buyers to hidden liabilities such as compliance violations, lawsuits, misaligned compensation structures, or cultural dysfunction.
Adi and Cindy break down the three essential HR vantage points for exit readiness: compliance, culture, and best practices. Compliance ensures risk is minimized through proper documentation and lawful employment practices. Culture ensures that leadership strength, employee engagement, and retention metrics are attractive to a buyer. Best practices focus on organizational design, scalable systems, and leadership structures that allow the company to operate independently of the founder.
The conversation reinforces a powerful systems principle: when the people side of the business is structured correctly, transitions are smoother, value increases, and owners can exit without being pulled back in. HR is not an afterthought—it is infrastructure that protects the transaction.
Resources mentioned in this episode:
Quotable Moments:
- “There are hidden HR liabilities that buyers don’t even know to ask about.”
- “Compliance, culture, and best practices are the three HR pillars of exit readiness.”
- “If your leadership team isn’t A++, your business isn’t exit-ready.”
- “One small lapse in HR due diligence can take down a deal.”
- “When you get the people part right, transitions are smoother and investments are protected.”
Action Steps:
- Conduct an HR compliance audit before entering exit discussions.
- Measure retention and engagement to assess cultural strength.
- Build leadership depth so the business can operate without you.
- Document repeatable systems that will last 3–5 years post-acquisition.
- Partner with HR experts during pre-due diligence, not after problems arise
Sponsor for this episode:
This episode is brought to you by Business Success Consulting Group.
At Business Success Consulting Group, we create custom processes and tailor-made management systems so businesses can thrive.
Businesses simply can’t survive without workable systems and well-documented processes. That’s why our team of experienced professionals takes care of it for you.
We provide business owners, entrepreneurs, and key executives with six phases to success, along with the long-lasting systems necessary to support business expansion.
So, what are you waiting for? Do yourself a favor and cut the chaos out of your business.
Visit bizsuccesscg.com today or email info@bizsuccesscg.com to schedule a free consultation.
