Protecting Cross-Border Deals from the Inside Out with Stephanie Pimentel

In this episode of the DealQuest Podcast, I'm thrilled to welcome Stephanie Pimentel, founder and CEO of Lumena Global Advisory, a boutique firm specializing in Latin American market entry, cross-border workforce strategy, and expansion risk management. With an executive background in multinational operations and human capital leadership, Stephanie has advised U.S. companies, private equity groups, and growth-stage founders on structuring compliant, scalable operations across Mexico, Colombia, Brazil, and beyond. A Dominican-American executive with degrees in human resource management and forensic psychology, she combines behavioral insight, compliance strategy, and 17 years of lived international experience to guide responsible global growth.

Stephanie started her career as an HR coordinator earning $11.75 an hour in New York, moved into telecommunications, then logistics, and eventually found herself navigating cross-border operations as the ports she worked with crossed into international territory. That journey built something most advisors don't have: direct, hands-on relationships at every level of business in Latin America, from CEOs down to the people actually running daily operations on the ground. In this conversation, we go deep on workforce liabilities, cultural misalignment, regulatory exposure, and what companies need to do before and after a cross-border transaction to actually protect the deal they worked so hard to close.

LATIN AMERICA IS NOT ONE MARKET

One of the most common and costly mistakes I see companies make when expanding into Latin America is treating the region as a single, uniform market. Stephanie puts it plainly: if you categorize Latin America as one whole, that is where most companies mess up. The legal structures for hiring in Mexico look nothing like what you'd encounter in Brazil, and both are entirely different from Chile or Argentina. Workforce culture, regulatory environment, compliance expectations, and even how authority is respected vary dramatically from country to country.

Stephanie has built 17 years of relationships across these countries, sitting down with CEOs and spending time with the people actually running the floor. That range of relationship is exactly what it takes to genuinely understand what you're walking into. Companies that rely solely on their in-house team or a general international consultant often discover the differences only after the deal is signed, and by then, it's expensive.

THE WORKFORCE LIABILITIES HIDING IN PLAIN SIGHT

Stephanie shared a case where a U.S. company acquired a majority stake in an overseas company. The historical financials looked solid. After close, the operation was bleeding cash and the workforce systems were completely misaligned. She was brought in to rebuild from an HR and operations standpoint, restructure roles, stabilize payroll, and fix the human systems holding performance back.

The issue was not that professionals weren't involved. Lawyers, accountants, and possibly investment bankers were all at the table. The problem was that nobody was asking the right questions about workforce governance, and nobody knew what to look for in that specific country. As Stephanie said, "In that specific country, there was no take-backsies." The deal was closed, the exposure was real, and the cleanup began. The good news is that she was able to fix it. But the better outcome is catching these issues before the ink dries.

A PROPRIETARY AUDIT THAT SCORES DEAL READINESS

To address the gap she kept seeing, Stephanie developed a proprietary audit system built around five pillars she measures against every cross-border deal: workforce governance, tax and regulation, financials, cultural fluency, and operational infrastructure. The system includes 40 questions, each with the potential for a disqualifying event, and at the end, she can tell you whether you're ready to expand, what needs to be fixed first, and what to expect in a specific country once you get there.

The audit generates a clear expansion roadmap before any capital is deployed. It covers country selection, risk mapping, operating model design, and workforce and talent architecture. For companies that need to go back to investors or PE firms, Stephanie's report gives them an airtight picture of where they stand. She makes the judgment call on readiness so the company can go in informed, not surprised.

BRAZIL'S $250,000 WRONG HIRE PROBLEM

One of the most striking examples Stephanie shared was a company doing a deal in Brazil that hired incorrectly due to a misaligned workforce structure. Brazil charged them $250,000 per wrong hire. That is not a penalty in the punitive sense most U.S. executives would expect. Brazil has mandatory employee benefits that must be set up before the hire, including things like a lunch stipend, that simply do not exist in the U.S. framework. When those structures are missing, the government fees come in, and they come in per employee.

This is the kind of liability that standard due diligence in a cross-border deal rarely surfaces, because the in-house team doing the review does not know what they do not know. They are checking what matters in a domestic context, not what matters in Brazil specifically. Stephanie's approach is built around knowing the difference between those two things in each country where she works.

CULTURE IS AN OPERATING SYSTEM, NOT A SOFT SKILL

When the topic of cultural differences came up, Stephanie said something that stays with me: "Culture is not values on a wall. Culture is how decisions get made when no one's watching." That is not a philosophical observation. It is a description of operational risk.

She gave a concrete example of a U.S. leadership team that valued direct confrontation and flat hierarchy walking into a Brazil operation where the local team operates through indirect communication and structured authority. When you do not account for that difference, you end up with retention issues, productivity problems, and compliance gaps. And turnover in Latin America is massively expensive because you owe a significant amount when someone leaves, regardless of how the departure happens.

Stephanie's view is clear: "Culture is not a soft risk. It is an absolute multiplier." When cultural alignment is present, growth accelerates, loyalty builds quickly, and people stick around. When it is misaligned, it burns capital fast and the damage does not show up on spreadsheets until it is already too late to prevent easily.

DIAGNOSE BEFORE YOU DEPLOY CAPITAL

When I asked Stephanie what companies that have done it right actually look like, her first answer was direct: diagnose before you deploy capital. Map the decision-making norms, hierarchy expectations, communication styles, conflict tolerance, and regulatory behavior of the market before you enter it. These problems do not surface until after you have signed, so the only way to get ahead of them is to do the work before you commit.

She added that companies need to redesign their leadership behavior for the specific region and resist the instinct to copy-paste the U.S. management approach. "Don't copy-paste U.S. leadership style," she said, "it won't work." And she made a point that I found particularly important: compliance in many Latin American markets is way more flexible than U.S. companies expect. Installing rigid U.S. compliance policies immediately without modeling that behavior at the leadership level creates friction before operations even get off the ground.

WHEN AN EMPLOYER OF RECORD MAKES SENSE (AND WHEN IT DOESN'T)

A common early move for companies exploring Latin American talent is using an EOR, an employer of record, as a way to test the market without setting up a legal entity. Stephanie acknowledges this can work as a short-term tool to reduce early-stage legal friction and test market fit. But she is clear that it is not a sustainable long-term strategy, and staying in that structure too long creates real problems.

The practical risk she highlights is misclassification exposure. Local labor laws do not disappear just because you are using an EOR, and that ignorance creates liability. The less obvious risk is cultural distance. If you are operating through an EOR for an extended period, you are not building genuine understanding of the market or its people. By the time you try to transition to a direct entity structure, you are behind on the cultural groundwork that should have been laid much earlier. The EOR is a bridge, not a destination.

DUE DILIGENCE ON THE DUE DILIGENCE

Cross-border deals, particularly in Latin America, require a different standard of due diligence than domestic transactions. Stephanie describes it this way: in Latin America, it is double. "You have to do due diligence on the due diligence." Standard diligence processes are not built for the regulatory realities of these markets, and companies that rush because capital has been approved and a target country has been selected often find out what they missed after close.

This applies specifically to third-party intermediaries. Having a local contact who knows the market can be genuinely useful, but companies need to be rigorous about who they are working with and what that person is doing on their behalf. Stephanie's solution is to bring her own vetted network of finance, HR, legal, and operations professionals with boots on the ground in each country where she operates. That includes Brazil, Chile, Argentina, Dominican Republic, and Costa Rica. Companies working with her avoid the problem of unknowingly inheriting exposure through an intermediary they did not properly vet.

GLOBALIZATION IS NOT SLOWING DOWN

There is a narrative that geopolitical tension, pandemic-era supply chain disruption, and political pressure toward onshoring are putting the brakes on global expansion. Stephanie pushes back on this directly. "I think it's unavoidable, and if anyone who's out there thinks that it's slowing down, they're absolutely wrong." She sees more smaller businesses expanding internationally now than ever, driven by greater access to information, nearshore talent availability in compatible time zones, and the growing visibility of labor arbitrage opportunities.

Her practical guidance for smaller companies is to expand in layers, not in leaps. Stabilize your domestic revenue first, document your operating model, and build a clean framework before crossing borders. Larger companies can absorb the cost of mistakes. Smaller ones cannot. That does not mean smaller companies should stay home. It means they should go in prepared. For companies thinking through where to start, Stephanie also notes that specific regions offer specific talent niches. Data center operations fit well in Brazil or Chile. Back-office support is well suited to the Caribbean. Country selection should match your actual business need.

WHAT LEADERSHIP READINESS ACTUALLY MEANS

One of the things Stephanie keeps returning to is the question of whether a leadership team is actually ready to execute across borders. Financials can be strong, operating systems can be solid, and compliance can be in good shape. None of it matters if the leadership team is not equipped for the environment they are entering.

She describes most executive teams as trained for predictable markets, centralized operations, and domestic growth. They have not been exposed to political volatility, the pace at which AI is accelerating cross-border workforce complexity, or the governance realities of these markets. The right preparation is not just cultural sensitivity training. It is building maturity, direct experience, and cultural awareness before the deal is done, not after. She is blunt about the consequence of skipping it: "If your leadership team is not ready to deploy, the deal won't be successful."

FREEDOM, A SEAT AT THE TABLE, AND BUILDING ON YOUR OWN TERMS

I close every episode by asking my guests what freedom means to them, because it is my highest value. For Stephanie, freedom means finally having what she describes as "the real seat at the table." She spent years in leadership roles early in her career noticing that the seat was sometimes offered for the wrong reasons, where you look good for a checkbox but are not actually given the space to share your talents or speak up. Branching out and building Lumena Global on her own terms changed that. She has felt the value of that real seat, and it is the driving force behind everything she has built.

Listen to the full episode of DealQuest Podcast with Stephanie Pimentel: [Available on all major podcast platforms]

FOR MORE ON STEPHANIE PIMENTEL
LinkedIn: https://www.linkedin.com/company/lumena-global
Company: https://lumenaglobal.com

FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

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