Enterprise Sales Strategy Trust Driving C-Level Growth

Discussion with Eduardo Angulo

With over three decades of experience leading sales in Latin America, the United States, and Europe, Eduardo Angulo has seen firsthand how enterprise relationships are won, and lost, at the executive level. From his early days with Sonda and Hewlett Packard in Chile, to global account leadership at Hitachi Vantara, and now as founder of his own consulting firm, Angulo has worked across various industries including telecom, banking, and manufacturing, building multi-million-dollar deals rooted in trust, alignment, and cultural understanding. In this article, he shares hard-earned lessons on how executives should approach relationship-building, stakeholder management, and trust as the ultimate drivers of long-term growth in enterprise sales.

Building Executive Trust in Enterprise Sales

Executives do not waste time or patience on unfocused conversations. To truly engage them, sales leaders must enter the room with substance, equipped not only with an understanding of the company’s strategy, objectives, and competitive environment, but also with insights into its industry pressures and competitive dynamics. “The first priority is to thoroughly understand the company and what the client is doing. When speaking with C-level executives, there is no room for small talk or digressions; they expect the conversation to be direct, relevant, and to the point”.

Preparation becomes the gateway to credibility. By demonstrating fluency in the client’s priorities and aligning your proposal with their long-term goals, you transition from being a vendor to a trusted advisor. Executives evaluate not just the content of a pitch, but whether it reflects an understanding of where their organization is heading and what obstacles they face. If a meeting does not deliver that level of relevance, it ends quickly. This ruthless efficiency means that salespeople must treat every interaction as a high-stakes opportunity.

At the same time, trust is never built in a single meeting. It is reinforced through consistency, delivering on promises, following up with substance, and keeping the client’s evolving priorities at the center of the conversation. Angulo highlights that when value is missing, “they will cut immediately”. The executive suite operates with constant scrutiny, so credibility can be lost in seconds if preparation falters. 

Adapting Sales to Global Cultural Contexts

Angulo’s career has spanned geographies with strikingly different business cultures, from North America’s efficiency-driven pace to Latin America’s relationship-oriented approach. He insists that while preparation is universal, the style of engagement varies according to context. “In the US, if a salesperson fails to provide clear value during a conversation, a CXO will end the discussion promptly”. In contrast, in Chile, as Angulo explains it “CXOs are far less likely to cut a meeting short; instead, they may continue granting time repeatedly, even when the dialogue is not progressing toward meaningful outcomes”.

In the United States, executives expect concise, data-backed proposals that demonstrate tangible impact quickly. Meetings are shorter, decision cycles are more defined, and dismissals are more direct. In Latin America, the dynamic is more personal, leaders are willing to give more time to build rapport, but this can mask disinterest if salespeople confuse politeness for genuine intent. Understanding this difference helps prevent wasted cycles and ensures conversations move toward concrete outcomes.

Success depends on knowing how executives process information, balance personal versus professional rapport, and weigh long-term trust against short-term efficiency. High-performing teams not only research the company but also map the career history and cultural context of decision-makers, often through tools like LinkedIn and industry networks. This layered preparation transforms surface-level meetings into meaningful executive dialogues.

Winning and Losing Enterprise Sales Deals

Angulo recalls one landmark transaction in which his team invested more than a year building credibility with both executives and end users across Latin America, the U.S., and Spain. The deal, worth more than $20 million, involved the complex task of consolidating regional data centers into unified hubs in two countries. Despite months of rigorous technical and commercial alignment, a competitor undercut pricing at the last moment and initially won. “Our proposal consisted of two large folders filled with detailed technical analysis. By contrast, the competitor submitted a last-minute offer with a more limited technical description. Faced with a 20% lower price, the client found it impossible to refuse”.

The loss underscored a hard reality: even the strongest trust and preparation can be overshadowed by cost pressures in procurement-driven environments. Yet the story demonstrates the long game of enterprise sales. Two years later, the same client, disappointed with the competitor’s delivery, returned to Angulo’s team and awarded them the deal at better margins. This reversal confirmed that execution, value, and credibility carry more weight over time than short-term price concessions.

For C-suite leaders, this example reinforces the importance for sales teams to cultivate multi-level alignment, not only at the executive level but also with technical decision-makers and end users. Without their support, even a CEO’s endorsement cannot secure the deal. As Angulo stresses, “The C-level can help you, but the decision makers, the end user, are the ones that can say no to your solution”. Big enterprise deals demand patience, comprehensive stakeholder management, and resilience in the face of setbacks, with trust serving as the long-term differentiator. 

Executives feel valued when their peers are engaged; technical staff trust peers who can speak their language. Angulo notes, “They feel that you care about them. If you are the only one in the relationship, sometimes it is not enough”. Enterprise sales is a team sport, and only by covering all bases can providers maintain control.

Coaching the Next Generation of Enterprise Sales Leaders

Not every salesperson is equipped to operate at the executive level, and this is where targeted coaching makes a difference. Angulo insists on rigorous preparation, structured development, and a mindset shift for those aiming to sell to the C-suite. “The first thing is they have to know the ABCDs of your client”. For Angulo, salespeople must truly understand their client before approaching the C-suite. That means knowing the client’s objectives, the areas of the business most affected, the competitive landscape, their most urgent challenges, and which departments are impacted. “If the salesperson can confidently answer those questions, then I can determine they are ready to engage with the CXO”. Only with this knowledge can proposed solutions align with both strategy and operations.

He recounts coaching a junior colleague in Chile who arrived at a high-level meeting armed with product brochures. Recognizing the mismatch, Angulo intervened, discarding the materials, and redirected the focus to building rapport and trust with the executive. “The conversation began with personal topics, family, sports, and other matters, before briefly touching on the product”. The lesson was clear: C-level engagement is not about features but about vision, alignment, and how solutions enable competitive advantage.

Sales leaders must therefore cultivate two complementary coaching tracks, one focused on technical credibility and product knowledge for middle management conversations, and another centered on strategic alignment, business outcomes, and relationship building for executives. This dual approach ensures sales teams can navigate the full spectrum of stakeholders without oversimplifying for executives or overwhelming technical buyers.

The Future of Trust in Enterprise Sales

Looking ahead, Angulo predicts that trust will only grow in importance as procurement pressures intensify and budgets tighten. Executives and procurement leaders now have access to abundant information, advanced benchmarking tools, and AI-driven analytics, forcing providers into increasingly competitive negotiations. “Today, everyone has access to comprehensive information about current market conditions. Procurement departments are under significant pressure to deliver improvements, making negotiations increasingly stressful for all parties involved”, Angulo remarks.

In this environment, small margins separate winners from losers. A 5% pricing advantage can tip the balance, but price alone rarely secures long-term success. Trust, built through years of consistent delivery, cultural awareness, and executive-level alignment, remains the key factor that brings clients back even after initial losses. Procurement’s emphasis on immediate savings will persist, but executives ultimately prioritize providers who demonstrate reliability, innovation, and the ability to address business-critical challenges.

For sales leaders, the next three to five years will demand sharper negotiation skills, stronger cross-functional collaboration, and continuous monitoring of client objectives that shift more often than before. Building resilience amid margin pressure and embedding trust into every interaction will separate high-performing teams from the rest. Trust will not only remain the currency of enterprise sales, it will also become the key factor in winning and sustaining high-stakes deals.

Key Takeaways for Enterprise Sales Executives

Angulo leaves leaders with three core lessons:

• Know your client, deeply and continuously: Strategic objectives now shift quarterly, requiring constant monitoring and alignment.
• Never sell what you cannot deliver: Short-term wins that fail to solve client problems destroy long-term trust.
• Set realistic targets and coach deliberately: Unrealistic expectations drive sales attrition; tailored coaching ensures alignment with both company culture and client needs.

As Angulo concludes, “It is essential to ensure that any offer is closely aligned with the client’s specific needs. Securing a major deal today means little if, within a few years, the account is lost due to misalignment”. Trust, once again, proves to be the ultimate competitive advantage.

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