Business Growth Strategies For CEOs: Top CMOs On Marketing Strategy Implementations

How to Engage Hard-to-Reach CXOs: The New Growth Playbook

Written by Ron Greenberg | Mon, Oct 26, 2026

 

This blog is part of Chief Outsiders’ New Growth Imperative series, designed to help CEOs and leadership teams engage executive decision-makers at targeted strategic accounts by turning deep insights into compelling customer value.

How to Engage Hard-to-Reach CXOs: The New Growth Playbook

How to convert deeper customer insights into CXO engagement and new, profitable growth opportunities

Most CEOs and growth leaders know which companies and executives they most want to engage, win, expand, and help succeed. The harder challenge is earning meaningful meetings and discussions with the senior executives who can open those opportunities.

Those executives have no shortage of companies seeking their attention. What earns their time is relevance: a perspective that demonstrates you understand their business, highlights an important issue or opportunity, and offers ideas that could improve performance or drive growth.

That raises an important question for leadership teams to consider:

Can we develop a deep enough understanding of a customer’s business to provide its executives with recommendations or ideas they will genuinely value?

Achieving this consistently requires a deeper understanding of customers and the ability to translate that understanding into high-value executive conversations. Teams can build this capability to bring more relevant ideas to executives, uncover new opportunities, and strengthen customer relationships over time.

The Insight That Matters

Most organizations already know a great deal about their selected strategic accounts, including size, industry, executives, technologies, recent news, intent signals, and prior interactions.

Insights are most valuable to customers when they’re positioned to offer fresh perspectives. They connect developments across the company, industry, customers, competitors, financial performance, and executive priorities to their business implications. We should ask:

What is changing? Why does it matter? What might we and our customers do about it? Where could we contribute something distinctive?

That interpretation creates a different type of CXO conversation. This enables your team to enter with an informed point of view, validate it with the lead executive, listen for what research could not reveal, and determine whether your expertise can help the customer achieve a better outcome.

Doing this well requires judgment, confidence, and practice. Teams must learn to synthesize information, form a point of view, test it constructively with senior leaders, and recognize opportunities as the conversation unfolds.

When Insight Changes the Relationship

I experienced this while leading global marketing at a media technology company.

Our customers knew we understood their technology and workflows. But conversations revealed a deeper issue affecting their business, including technology: they were being asked to produce higher-quality content more quickly even as budgets, schedules, and staffing tightened.

We developed executive briefings in key cities around the world to address those pressures, brought in an independent industry expert, and invited a respected customer executive to share how his company was grappling with similar challenges. We set the business context and reviewed our customers’ lived experiences before discussing how our capabilities could help.

Senior executives who had previously resisted product-focused meetings attended these issue- and solution-focused sessions and even initiated follow-up conversations. These insights led to our deliberate shift toward solutions, creating a program that generated and closed millions of dollars in opportunities not previously in the pipeline and, most important, helped current and new customers successfully address their issues.

The products and technology remained largely unchanged. However, our understanding of the customer, along with the ideas and value we brought to executive discussions, had evolved significantly.

Putting the New Growth Playbook to Work

For CEOs, the opportunity is to make this capability intentional and repeatable. I recommend four leadership actions.

  1. Focus on where growth matters most. Select a manageable number of prospective and current accounts where greater executive access could drive meaningful growth, expansion, or market entry.
  2. Develop insights worth sharing with the executive. Combine company, industry, competitive, customer, and executive intelligence to identify issues and opportunities with real business significance. Doing so effectively requires deep knowledge of the company and its challenges.
  3. Build the capability for high-value conversations. Test sales, marketing, executive leaders, and subject-matter experts by asking challenging questions and reviewing content to help them translate insights into informed perspectives. Use this approach to engage senior customer executives on their priorities and desired outcomes.
  4. Organize around the opportunity. Align the right people, expertise, content, proof, and follow-through across the buying group to drive engagement toward meaningful action.

For selected high-value accounts, value-led Account Based Marketing provides the structure for turning customer insight into executive engagement and growth—aligning the right perspectives, content, and actions around the opportunities most likely to create new value.

Forrester similarly points toward ABM centered on customer value and profitable growth. ¹ ² Accenture reports that 50% of B2B buyers say collaboration and cross-functional complexity are making purchasing decisions more difficult, reinforcing the need to align around the most important issues and growth opportunities across the buying group.³

AI Can Deepen the Preparation

AI can support GTM leaders by synthesizing company, industry, competitive, customer, and buyer intelligence, identifying patterns, and delivering more relevant insights.

McKinsey’s 2026 B2B research found that buyers now use an average of ten channels throughout the purchasing journey, underscoring the need for consistent information and expertise across all interactions. ⁴

Platforms such as Chief Outsiders’ GrowthGears OS can enable more comprehensive research, preparation, and personalization for targeted high-value accounts, thereby improving outcomes.

From Insight to Growth

The playbook is conceptually straightforward:

Insight → Executive Value → Engagement → Action → Growth

Building it effectively requires a substantial initial investment of effort: selecting the right accounts, developing deeper insight, strengthening executive-level communication skills, aligning teams, and following through with discipline.

The result is a more consistent approach to engaging hard-to-reach CXOs, cultivating strategic relationships, and driving profitable growth across the accounts and markets that matter most.

Ask your leadership team:

Do we have the insight, skills, and operational capability to consistently deliver value to the CXOs we most want to engage?

The three-minute Value Advantage Assessment™ can identify where your organization is strongest and where targeted action could have the greatest impact.

I work with CEOs and GTM leadership teams to build these capabilities and translate them into a Value-Led ABM approach tailored to their priority accounts, target executives, and growth opportunities.

 

Catch Up on the Full Series

 

Sources

  1. Forrester, ABM Won, But It’s Not Done Changing the Game, 2024.
  2. Forrester, The Future of Account-Based Marketing Isn’t Scale — It’s Profitable Growth, 2024.
  3. Accenture, B2B Customer Growth / Client Buying Index, 2025.
  4. McKinsey & Company, The Surprising Economics of B2B Growth, 2026.