Picture this: You've calendared a QBR with your key account's CMO. Your stomach drops a little. Should you bring your AE? What metrics do they actually care about? Will they even remember who you are from the last call six months ago?
If this scenario sounds familiar, you're not alone. Most CSMs feel intimidated when it comes to engaging with C-level executives. But here's what I've learned after years of managing enterprise accounts: executives are just people with really expensive problems to solve. And if you can help solve those problems while demonstrating clear business value, you'll find they're often your biggest advocates.
The reality is that C-level engagement isn't optional anymore—it's essential. As customer success moves upmarket, CSMs will likely assume responsibility for interacting with senior stakeholders, including C-suite executives, VPs, and other senior executives. But most CSMs struggle with when to engage, how to add value, and what executives actually care about.
The stakes couldn't be higher. According to industry research, executive turnover is one of the leading causes of customer churn. When you lose your executive sponsor, you're not just losing a relationship—you're losing the strategic alignment that keeps your partnership defensible.
Let me share the framework I've developed for building meaningful executive relationships that drive results throughout the entire customer lifecycle.
The Foundation: Understanding What Executives Actually Care About
Before we dive into tactics, let's get one thing straight: The most obvious and important data point for any C-Suite executive is the impact of your solution on their revenue and profit. How much will your solution increase their sales, reduce their costs, or improve their margins?
Everything else is secondary. Executives don't care about your product features, your training sessions, or even your customer health scores unless they directly tie to business outcomes.
This means your executive engagement strategy needs to be built around three core pillars:
Revenue Impact: How are you driving growth or preventing revenue loss?
Operational Efficiency: How are you helping them do more with less?
Strategic Alignment: How does their partnership with you advance their broader business objectives?
The Executive Engagement Framework
When to Engage: The 4 Critical Touchpoints
1. Onboarding & Early Value Realization (Months 1-6) Don't wait until your champion suggests it. Proactively schedule time with the executive sponsor who signed the contract. They have skin in the game and want to see early wins.
2. Mid-Cycle Value Validation (Every 6 months) The ideal frequency for your EBRs depends on account size, complexity, and lifecycle stage. Most organizations follow these guidelines: Strategic accounts: Bi-annual EBRs (every 6 months) This is your strategic alignment check-in where you validate priorities and surface new opportunities.
3. Expansion & Growth Conversations (Ongoing) When usage data shows expansion potential or when they hit certain milestones, bring executives into the conversation early.
4. Renewal & Strategic Planning (12+ months before renewal) Start planting seeds early. Executives need time to budget and plan for the following year. Their budget will focus on areas where they know value and returns are being generated—ensure they understand how your product supports them in these areas.
Why Executives Should Care: The Value Exchange
Stop thinking about these as "check-ins" and start thinking about them as strategic advisory sessions. You have a unique vantage point:
You see how they compare to industry benchmarks
You understand their operational challenges intimately
You know what's working (and what isn't) across their organization
You have insights from similar customers they can learn from
Frame every interaction around the value you're uniquely positioned to provide, not the value you hope to extract.
How to Engage: Executive Presence Without the Intimidation
The Mindset Shift
These executives have the power to champion a customer-centric mindset throughout your entire organization. By setting the tone at the top and emphasizing the importance of putting the customer first, C-suite executives can create a culture that prioritizes customer success. You're not asking for their time—you're offering them strategic value.
Mastering Executive Communication
The difference between CSMs who thrive in executive meetings and those who struggle often comes down to communication technique. Here are specific methods that separate confident executive communicators from the rest:
Lead with Executive Summaries:
Wrong: "Let me walk through our 47 different metrics..."
Right: "Revenue attributed to our platform increased 23% this quarter—let me show you the three drivers behind that growth."
Translate Everything to Business Impact:
Wrong: "User adoption increased 15%"
Right: "The 15% increase in user adoption is driving $50K in additional pipeline this quarter, putting you 12% ahead of your yearly target."
Use the 'So What?' Test:
Wrong: "You have 847 active users this month"
Right: "847 active users represents 94% of your target audience—meaning we've successfully scaled adoption across your entire go-to-market organization, which correlates to the 23% pipeline increase you're seeing."
Frame Around Their Goals:
Wrong: "Our platform processed 10,000 transactions"
Right: "The 10,000 transactions we've processed saved your team an estimated 200 hours this month—that's 5 weeks of additional capacity you can redeploy toward your Q4 market expansion."
Pre-Meeting Preparation That Commands Confidence
I use this template for every executive meeting:
Executive Meeting Prep Template:
Business Context: What's happening in their industry/company right now?
Success Metrics: What 2-3 KPIs matter most to them? (Validated with champion)
Value Delivered: Specific wins/outcomes achieved in the last 6 months
Strategic Insights: 2-3 observations or benchmarks they can act on
Clear Ask: What specific outcome do I want from this meeting?
The Meeting Structure That Works
Start with Results (2 minutes): Lead with the business impact you've delivered
Strategic Context (3 minutes): Share relevant industry insights or benchmarks
Future Opportunities (10 minutes): Present 2-3 strategic recommendations
Partnership Discussion (10 minutes): Align on priorities for the next 6 months
Clear Next Steps (2 minutes): Confirm commitments and timeline
What to Discuss: The Executive Conversation Framework
Tier 1 Metrics: Revenue & Growth
Revenue attributed to your platform
Cost savings/operational efficiency gains
Market share or competitive positioning improvements
Customer acquisition or retention improvements driven by your solution
Tier 2 Metrics: Strategic Alignment
Progress toward stated business objectives
Performance vs. industry benchmarks
Time to value improvements
Process improvements that scale across the organization
Tier 3 Metrics: Operational Excellence
User adoption and engagement trends
Support efficiency gains
Training/enablement ROI
Cross-functional collaboration improvements
Notice what's NOT on this list: feature adoption, training completion rates, support ticket volume. The C-suite is often time-poor. Lead with the key number such as profit/revenue and only then provide the detail. These operational metrics only matter if they directly tie to the business outcomes above.
The Champion Connection: Your Secret Weapon
None of this works without a strong champion relationship. Your champion is your executive intelligence network—and misaligned metrics can derail your credibility faster than anything else.
The Credibility Killer Scenario
Imagine this: You've spent weeks preparing a presentation focused on user adoption statistics, highlighting a 20% increase in monthly active users. You walk into the executive meeting confident, only to hear the CFO interrupt three minutes in with, "That's great, but how does this affect our margin? We're being asked to cut 15% from operational costs this quarter."
That's a credibility hit you could have avoided with proper champion preparation. Your champion would have told you that cost reduction, not growth metrics, was top of mind for the executive team that month.
Champion Validation Process
Every month, I validate executive priorities with my champions using this framework:
"Based on our last conversation with [Executive], I'm planning to focus our next update on [specific metrics/outcomes]. Does that still align with what matters most to them right now? Is there anything else I should be highlighting or any concerns I should be addressing?"
This 2-minute conversation can save you from presenting the wrong metrics to an executive and losing credibility. But here's the secret: champions benefit when you make them look good. When you showcase their team's impact to executives, you're giving them ammunition for their own performance reviews and career advancement. Frame your champion relationship as a mutual success partnership.
Champion Intel Questions
"What metrics is [Executive] getting asked about by the board/CEO right now?"
"If [Executive] had to pick one business challenge keeping them up at night, what would it be?"
"When [Executive] talks about our partnership internally, what language do they use?"
"What would make [Executive] look like a hero in front of their peers?"
The Strategic Bi-Annual Alignment Process
Executive business reviews are strategic, outcome-focused meetings that help you connect day-to-day efforts to your customer's long-term goals. Unlike QBRs, EBRs are built for executive audiences and focus on business impact rather than product usage.
Here's how the cadence should work:
Timing | 6-Month Alignment | 12-Month Strategic Planning |
|---|---|---|
Primary Focus | Value validation & course correction | Strategic planning & partnership evolution |
Meeting Length | 45 minutes | 60-90 minutes |
Audience | Executive sponsor + key stakeholders | Executive team + decision makers |
Agenda Split | 30% recap, 70% forward-looking | 20% recap, 80% strategic planning |
Key Deliverable | Refined success metrics & priorities | Annual partnership roadmap |
Follow-up | Monthly executive brief updates | Quarterly milestone check-ins |
6 Months: The Value Validation Check-In
Agenda Framework:
Scorecard Review (10 minutes): Present performance against originally agreed-upon success metrics
Strategic Insights (15 minutes): Share 2-3 benchmarks or trends relevant to their industry
Mid-Course Corrections (15 minutes): Address any shifted priorities or market changes
Optimization Opportunities (5 minutes): Present specific recommendations for improvement
Key Question to Answer: "Are we still solving the right problems in the right way?"
12 Months: The Strategic Planning Session
Agenda Framework:
Annual Value Review (15 minutes): Comprehensive ROI analysis of the partnership
Market Context (20 minutes): How they're positioned vs. their market
Growth Strategy (30 minutes): Recommendations for expanding value in the coming year
Partnership Evolution (15 minutes): How can the relationship better support their strategic objectives?
Key Question to Answer: "How do we deepen this partnership to drive even more strategic value?"
Handling Mid-Year Priority Shifts
When executives tell you that cost-cutting has overtaken growth as the priority, don't panic. This is your opportunity to demonstrate strategic agility:
Acknowledge the shift immediately: "I understand cost optimization is now the top priority. Let me reframe our partnership value around efficiency gains."
Pivot your narrative: Move from growth metrics to operational efficiency, cost per transaction, or process automation benefits.
Provide immediate value: "Based on this new priority, here are three ways we can help you achieve those cost reduction targets..."
This kind of responsiveness separates strategic partners from vendor relationships.
Maintaining Ongoing Executive Engagement
The Monthly Executive Brief
Between your bi-annual strategic sessions, maintain executive mindshare with a brief monthly update:
Subject: [Company] Platform Performance Update - [Month/Year]
Key Metrics Dashboard:
Metric 1: [Current Performance] vs [Target] vs [Industry Benchmark]
Metric 2: [Current Performance] vs [Target] vs [Industry Benchmark]
Metric 3: [Current Performance] vs [Target] vs [Industry Benchmark]
This Month's Wins:
Specific business outcome achieved
Process improvement implemented
Milestone reached
Strategic Recommendation: One actionable insight they can implement to drive better results
Next Month's Focus: Clear priorities aligned with their business objectives
This keeps you top-of-mind without overwhelming them with information.
Critical Pitfalls to Avoid
1. Leading with Features Instead of Outcomes Wrong: "We've increased user adoption by 15%" Right: "The 15% increase in user adoption is driving $50K in additional pipeline this quarter"
2. Over-Indexing on Usage Metrics This is the most dangerous trap for CSMs. Usage metrics feel safe because they're concrete and measurable, but they can actually damage your credibility if they don't tie to business outcomes. Executives care about results, not activity.
3. Over-Preparing Slides, Under-Preparing Narrative Many CSMs default to comprehensive slide decks, but executives often want the strategic narrative first and visuals second. Be ready to deliver your key points conversationally before diving into presentations.
4. The Executive Turnover Crisis
When you lose an executive sponsor, you have approximately 90 days to establish a relationship with their replacement before they begin evaluating all vendor relationships. Here's your playbook:
Immediate Actions (Week 1):
Get introduced through your champion or remaining contacts
Request a 30-minute "partnership overview" meeting
Prepare a concise executive brief on your partnership's value to date
30-Day Mark:
Present a comprehensive partnership assessment
Align on their priorities and success metrics
Propose an updated partnership roadmap
90-Day Mark:
Complete your first formal business review with the new executive
Establish your ongoing cadence
Secure their commitment to the strategic partnership
The key is speed and value demonstration. New executives are making vendor evaluation decisions quickly—make sure you're positioned as strategic, not tactical.
Long-Term Relationship Building That Drives Results
Executive engagement isn't a one-and-done activity—it's relationship building that compounds over time.
Advanced Relationship Building Strategies
1. Executive Sponsor Programs Pair your VP of Customer Success with their VP or C-level executive for quarterly strategic discussions. This creates a peer-level relationship that reinforces your importance as a strategic partner.
2. Customer Advisory Councils Invite your strongest executive relationships to participate in exclusive customer advisory councils. This gives them influence over your product roadmap while positioning them as industry thought leaders.
3. Strategic Introductions Become known as the CSM who makes valuable introductions. Connect your executives with:
Non-competing customers facing similar challenges
Industry experts and consultants
Potential partners or vendors in adjacent spaces
Speaking opportunities at conferences
4. Industry Intelligence Sharing Beyond your platform data, share relevant industry reports, competitive intelligence, and market trends. Position yourself as their trusted advisor for industry insights, not just your product.
5. Handling Disengagement Signals
When executives stop attending meetings or become less responsive, don't ignore it. Address it directly:
Immediate Response: Reach out within 48 hours to understand if priorities have shifted
Champion Intel: Work with your internal contacts to understand what's happening
Value Reset: Schedule a brief "partnership health check" to realign expectations
Executive Sponsor Escalation: If needed, have your executives reach out to theirs
The key is addressing disengagement proactively rather than letting relationships drift.
Building Your Executive Influence Network
Think beyond your primary executive sponsor. Build relationships across the C-suite:
CFO: Focus on cost savings, operational efficiency, and ROI metrics
CTO: Emphasize technical outcomes, integration success, and innovation enablement
COO: Highlight process improvements, scalability, and organizational impact
CRO: Demonstrate pipeline influence, sales enablement, and market expansion
Each relationship requires different metrics and messaging, but the collective influence makes your partnership virtually unshakeable.
Making It Actionable: Your 30-60-90 Day Plan
30 Days:
Audit your current executive relationships and identify gaps
Work with your champion to validate the top 3 metrics that matter to executives
Schedule your next executive check-in using the frameworks above
Create your executive meeting prep template
60 Days:
Implement the monthly executive brief process
Conduct your first strategic alignment meeting using the bi-annual framework
Document lessons learned and refine your communication techniques
Begin building your broader executive influence network
90 Days:
Evaluate the impact of increased executive engagement on your accounts
Expand the approach to additional accounts based on lessons learned
Share best practices with your team and create internal playbooks
Establish your ongoing cadence for strategic relationship building
The Bottom Line: Don't Gamble with Strategic Relationships
Here's the risk/reward reality: If you don't engage executives effectively, even strong user adoption and champion relationships can't save you when budget cuts come or strategic priorities shift. Your partnership becomes vulnerable to any leadership change, market downturn, or competitive threat.
But if you do master executive engagement, you gain more than just retention. You become integral to their strategic planning processes. Data-informed decision-making should be the main driver of all customer success strategies. Investment in customer success positions and experiences is paramount to helping a company thrive.
Your customers' executives are already making decisions that affect their relationship with you. The question is: are you in the room where it happens, or are you hearing about it secondhand?
The CSMs who thrive in the next evolution of customer success won't be the ones with the best user adoption metrics or the most product knowledge. They'll be the ones who can walk into any room, command executive attention, and drive strategic conversations that create mutual value.
Your immediate next step: Pick one account. Choose your strongest champion relationship and implement this executive engagement framework over the next quarter. Schedule that strategic alignment meeting. Start sending monthly executive briefs. Begin building your executive influence network.
The difference in how you're perceived, the influence you have, and the strategic impact you drive will be dramatic. Your renewal rates will improve, your expansion opportunities will multiply, and you'll become the kind of CSM that executives actively seek out as a strategic advisor.
Don't wait for permission to provide strategic value. If you're delivering results, executives want to hear from you. The only question is whether you'll have the confidence and framework to engage them effectively.