For twelve months, I'd email our CEO whenever I had competitive intelligence, customer insights, or market observations I thought he'd find valuable.
Some emails got responses ("interesting, thanks"). Most got silence.
I thought maybe my insights weren't valuable enough. Or maybe the CEO was just too busy to engage with PMM updates.
Then I watched a peer PMM become our CEO's go-to source for market intelligence. He'd reference her insights in exec meetings, forward her updates to the board, and consult her before major decisions.
I asked her how she'd built that relationship. She said: "I send him a structured monthly update. Same format, same time every month. He knows exactly when to expect it and what he'll get. That consistency builds trust."
I was skeptical. A monthly update sounded too rigid. Wouldn't it be better to send insights when they were fresh and relevant?
But I tried it. I sent my first structured monthly CEO update on January 15th. By March, the CEO was forwarding my updates to the exec team. By June, he was asking me to present my monthly insights at board meetings.
The difference: Structure creates trust. Consistency builds relationships. Predictability makes you indispensable.
Why Ad-Hoc Updates Don't Work (Even When They're Good)
What I was doing:
Whenever I learned something interesting, I'd email the CEO:
- "Saw this competitive move—thought you'd want to know"
- "Just finished win/loss interviews—here are key insights"
- "Customer told me something concerning about our positioning"
These were good insights. But they were random, inconsistent, and came at unpredictable times.
Why this doesn't work:
CEOs receive 100+ emails per day. Random updates get lost in the flood. Even when they read them, there's no context or pattern—just isolated pieces of information.
CEOs can't rely on you if they don't know when you'll surface information. Ad-hoc updates signal you're reactive, not proactive.
CEOs don't build trust with sources they can't predict. They build trust with people who show up consistently.
What changed when I switched to monthly structured updates:
- CEO knew exactly when to expect my update (3rd Monday of every month)
- He knew exactly what format it would be in (same structure every time)
- He could rely on me to surface important information systematically
- I became a predictable, trustworthy source instead of a random input
The Monthly CEO Update Format That Works
After testing different structures, I settled on this format. I've used it for 18 months. CEO reads it every month, forwards it to exec team 60% of the time, and references it in strategic conversations.
Subject: Market Intelligence Update – January 2025
TL;DR: Competitor X launching AI features Q2 (risk: $3.2M pipeline); Mid-market segment outperforming (opportunity: double down); Customer churn signals in enterprise (early warning).
1. Competitive Movement (What's Changed)
Competitor X Announces AI Features
- Launching Q2 based on their product roadmap and hiring signals
- Affects 40% of our deals where AI capabilities are evaluation criteria
- Risk: They'll have differentiation we don't in competitive evaluations
- Recommendation: Discuss mitigation options in Feb exec meeting (build vs. partner vs. reposition)
Competitor Y Raised $30M Series B
- Announced Jan 18; funding to expand enterprise sales team
- They're hiring 15 enterprise reps (2x their current team)
- Implication: Expect increased competitive pressure in enterprise segment over next 6 months
2. Win/Loss Patterns (What We're Learning)
Pattern: Mid-Market Overperforming
- Win rate: 61% (up from 58% in Q4)
- Average deal size: $185K (up from $170K in Q4)
- Sales cycle: 3.8 months (down from 4.2 months in Q4)
- Insight: Our "implementation speed" positioning resonates strongly in mid-market
Pattern: Enterprise Underperforming
- Win rate: 18% (down from 22% in Q4)
- Primary loss factor: Compliance requirements (SOC 2, HIPAA) we don't have
- Pipeline at risk: $3.2M annually
- Recommendation: Decision needed—invest in compliance or reposition away from enterprise
3. Customer Signals (Early Warnings)
Churn Risk in Enterprise Segment
- 3 of top 20 accounts mentioned evaluating alternatives in recent QBRs
- Pattern: All 3 cited expanding compliance needs we don't meet
- Revenue at risk: $2.4M (12% of ARR)
- Action: CS prioritizing retention plan for these 3 accounts
Positive Signal: Integration Depth Increasing
- 68% of customers now have 5+ integrations (up from 52% in Q4)
- Strong retention indicator—customers with 5+ integrations have 97% retention vs. 88% with fewer integrations
- Recommendation: Product should prioritize integration depth over breadth
4. Strategic Implications (What This Means)
Implication #1: Mid-Market is Our Competitive Advantage
- We're winning 61% of mid-market deals vs. 18% of enterprise
- Sales cycles 2x faster, win rates 3.4x higher
- Recommendation: Redirect 60% of sales capacity to mid-market from enterprise
Implication #2: Enterprise Requires Compliance Investment
- Compliance gaps causing 70% of enterprise losses
- Without investment, we'll continue losing enterprise deals
- Options: Build compliance ($600K, 12 months) vs. Reposition away from enterprise (immediate, $0)
5. Decisions Needed
Decision 1: Competitor X AI Response (Urgency: High)
- Need decision by Feb 15 to influence Q2 roadmap
- Options: Build AI ($2M, 18 months), Partner ($400K, 6 months), Reposition ($0, immediate)
- Recommendation: Partner approach—faster time to market, lower risk
Decision 2: Sales Capacity Allocation (Urgency: Medium)
- Should we redirect sales from enterprise to mid-market?
- Recommendation: Yes—data shows 3.4x higher win rate in mid-market
- Need approval to adjust sales territories in Q2 planning
Full Context: [Link to supporting documentation]
That's the format: Five sections, one page, scannable in 3 minutes, always includes decisions needed.
Why This Format Works (The Psychology Behind It)
Element 1: TL;DR at the top
CEOs scan, they don't read. TL;DR gives them the three most important points immediately.
If they want more detail, they keep reading. If they just need the headline, they're done in 30 seconds.
This respects their time and attention.
Element 2: Consistent structure every month
Same five sections, same order, every single month.
This makes it easy to scan. CEO knows exactly where to look for competitive updates (section 1), win/loss patterns (section 2), etc.
Consistency builds trust. They know what they'll get.
Element 3: Early warning system
Section 3 (Customer Signals) surfaces risks before they become crises.
CEOs appreciate when you bring forward problems early when they're still manageable, not after they've exploded.
This positions you as strategic advisor, not just reporter.
Element 4: Clear decisions needed
Section 5 explicitly states what decisions I need from the CEO.
This makes it actionable. CEO isn't left wondering "what do you want me to do with this information?"
Clarity drives action.
Element 5: Links to supporting detail
I don't include 40 pages of analysis in the email. I link to a shared doc with full context.
CEO can dig deeper if needed, but isn't forced to wade through detail.
This balances brevity with rigor.
The Timing That Makes It Reliable
I send this update the 3rd Monday of every month at 9 AM.
Same day. Same time. Every month.
Why this matters:
CEOs have patterns. Ours does strategic thinking Monday mornings. He reviews emails from the weekend and plans his week.
Sending my update Monday morning means it's fresh when he's in strategic mindset.
The consistency builds anticipation. By month 6, the CEO told me: "I look forward to your monthly update. It's one of the few emails I prioritize."
What to Include vs. What to Skip
After 18 months of monthly updates, here's what I've learned about what to include:
Include: Changes That Affect Strategy
- Competitive movements (funding, launches, positioning shifts)
- Win/loss pattern shifts (if win rate moves 5+ points)
- Customer signals indicating market shifts
- Early warnings about risks not yet on exec radar
Include: Decisions That Need CEO Input
- Resource allocation questions (where should we compete?)
- Budget decisions (should we invest in X?)
- Strategic choices (build vs. partner vs. reposition)
Include: Metrics Trends (But Not Raw Metrics)
Bad: "Win rate was 61% this month."
Good: "Win rate improved from 58% to 61%—pattern is mid-market deals are closing faster due to new positioning."
CEOs care about trends and patterns, not point-in-time data.
Skip: Tactical Execution Updates
- "We updated the battle cards" (unless it drove measurable impact)
- "We launched a new campaign" (unless it's generating strategic insights)
- "We hired a PMM" (CEO doesn't need this in monthly intelligence update)
Skip: Information CEO Already Has
If CEO was in the meeting where this was discussed, don't rehash it. Only include if you have new information or context he doesn't have.
Skip: "Good News" You Want Credit For
This isn't a brag document. This is strategic intelligence.
If something went well but doesn't inform future strategy, skip it.
How to Handle Months Where "Nothing Happened"
Some months, there's no major competitive movement, no dramatic pattern shifts, no urgent decisions.
Do you skip the update? No.
Consistency matters more than "having something important to say."
Here's how I handle quieter months:
Subject: Market Intelligence Update – October 2024
TL;DR: Quiet month on competitive front; Win/loss patterns holding steady; Focus on integration depth showing retention impact.
1. Competitive Movement: No major changes this month. Monitoring Competitor X's AI launch (still on track for Q2).
2. Win/Loss Patterns: Consistent with previous month—mid-market outperforming (61% win rate), enterprise underperforming (18% win rate). No new patterns emerged.
3. Customer Signals: Integration depth correlating strongly with retention—customers with 5+ integrations have 97% retention vs. 88% with fewer. Reinforces recommendation that Product prioritize integration depth.
4. Strategic Implications: Previous month's strategic implications still hold. No new data to change recommendations.
5. Decisions Needed: Still waiting on decision re: sales capacity allocation. No new urgent decisions this month.
Even in quiet months, the update reinforces:
- I'm systematically monitoring the market
- Previous strategic implications still hold
- No surprises—if something big was happening, I'd flag it
CEOs appreciate "nothing has changed" updates because it confirms you're watching and there's no hidden crisis.
The Follow-Up That Makes It Actionable
Sending the monthly update is step one. Following up on decisions is what makes it valuable.
In section 5 (Decisions Needed), I list what I need from the CEO.
If he doesn't respond within 3 days, I follow up:
"Subject: Following Up: Decision Needed on Sales Capacity Allocation
We discussed redirecting sales capacity from enterprise to mid-market in this month's intelligence update. Data shows 3.4x higher win rate in mid-market. Need decision by Feb 1 to adjust Q2 sales territories.
Can we get 15 minutes on your calendar this week to discuss?"
This converts the monthly update from information-sharing to decision-driving.
What Changed After Six Months of Monthly Updates
Month 1-3: CEO would read and occasionally respond "thanks for this."
Month 4-6: CEO started forwarding to exec team: "Good market intelligence from [my name]."
Month 6-12: CEO started referencing my insights in strategy conversations: "As [my name] noted in her monthly update..."
Month 12+: CEO started proactively asking me questions before making decisions: "What's your read on this based on what you're seeing in the market?"
The monthly update built a relationship that ad-hoc emails never did.
By showing up consistently with structured, actionable intelligence, I became a trusted advisor the CEO consulted on strategy.
The Template You Can Use
Here's the exact template I use. Adapt it to your context:
Subject: Market Intelligence Update – [Month Year]
TL;DR: [3 most important points in one sentence each]
1. Competitive Movement [2-3 most significant competitive changes this month]
2. Win/Loss Patterns [Key patterns from deals—what's working, what's not]
3. Customer Signals [Early warnings or positive trends from customers]
4. Strategic Implications [What this data means for company strategy]
5. Decisions Needed [Specific decisions you need from CEO with timeline]
That's it. Five sections, one page, sent same day every month.
The Uncomfortable Truth About CEO Updates
Most PMMs wait for CEOs to ask for information.
CEOs don't ask because they don't know what questions to ask—they need PMMs to surface what matters proactively.
The PMMs who build CEO relationships:
- Send structured monthly updates
- Focus on strategic implications, not tactical activities
- Surface decisions that need CEO input
- Show up consistently (same format, same timing)
- Follow up to drive decisions
The PMMs who don't build CEO relationships:
- Send ad-hoc updates when they have something to share
- Report on PMM activities instead of market intelligence
- Present information without asking for decisions
- Inconsistent communication
- Don't follow up
The difference in career trajectory is dramatic.
I went from sending emails the CEO rarely responded to, to becoming his primary source for market intelligence—all by switching to a structured monthly format.
The monthly update isn't just communication—it's relationship building through consistency, relevance, and actionability.
Start sending a monthly CEO update this format. Same day every month. Same structure. Always include decisions needed.
Within six months, you'll go from someone the CEO occasionally hears from to someone the CEO actively consults.
That's when your career accelerates.