The Slack message came at 4:47 PM on a Friday: "Can you present our competitive strategy at Monday's exec team meeting? 30 minutes. CEO specifically asked for you."
My immediate reaction was pride. The CEO wanted me to present competitive strategy to the executive team. This was my moment to show strategic value.
My second reaction, about ten seconds later, was panic. I had competitive intelligence—battle cards, win/loss data, feature comparisons. But I didn't have a competitive strategy.
I spent the entire weekend trying to figure out the difference.
By Sunday night, I had 47 slides covering our competitive landscape, recent losses, product gaps, and recommended feature additions. I felt prepared.
Monday morning, I presented for twelve minutes before the CEO interrupted: "This is all useful context, but what's your actual recommendation? Should we compete head-on with Competitor X, reposition to avoid them, or focus on a different segment entirely?"
I didn't have an answer. I had analysis, but I hadn't made the strategic choice that analysis was supposed to inform.
The CEO thanked me and moved on to the next agenda item. After the meeting, he pulled me aside: "You know more about our competitive position than anyone in the company. But I don't need more information—I need a recommendation on where we compete and where we don't. That's strategy."
That conversation changed how I approached every competitive presentation afterward.
What I Thought Competitive Strategy Meant (vs. What It Actually Means)
I thought competitive strategy meant having comprehensive knowledge of competitors' products, pricing, messaging, and roadmaps. The more I knew, the better the strategy.
That's competitive intelligence, not competitive strategy.
Competitive intelligence is understanding what competitors are doing.
Competitive strategy is deciding where you'll win and where you won't compete.
The CEO didn't need me to explain what competitors were doing—he needed me to recommend which battles to fight and which to walk away from.
That requires making uncomfortable choices:
- Should we compete in enterprise even though we're losing 70% of those deals?
- Should we match competitor pricing or hold our ground and lose price-sensitive deals?
- Should we build features to compete with Feature X or double down on our differentiation?
I'd spent years avoiding those questions by presenting "more analysis." The CEO's question forced me to stop analyzing and start recommending.
The Framework That Changed How I Present Competitive Strategy
After that failed presentation, I rebuilt my approach around a framework I wish I'd learned years earlier.
Every competitive strategy presentation needs to answer three questions:
Question 1: Where Are We Winning and Why?
Not "where could we win" or "where we should be winning." Where are we actually winning today, and what's the pattern?
For us, the answer was uncomfortable: We were winning in mid-market deals ($50K-$200K ACV) where buyers valued speed of implementation over enterprise features.
We were losing almost every enterprise deal ($500K+ ACV) where buyers needed compliance certifications we didn't have.
Why this matters: Strategy starts with understanding your actual competitive advantage, not your desired competitive advantage.
I presented this as one slide:
"Win rate by deal size:
- Sub-$50K: 68%
- $50K-$200K: 61%
- $200K-$500K: 34%
- $500K+: 18%
Pattern: We win when implementation speed matters more than enterprise compliance. We lose when enterprise certifications are required."
This framed the strategic question: Do we invest in enterprise capabilities to compete where we're losing, or double down on mid-market where we're winning?
Question 2: Where Are We Losing and What Would It Take to Win?
Not vague observations like "we need better features." Specific market segments where we're losing and the actual investment required to compete.
For enterprise deals, I broke it down:
"To compete in enterprise effectively, we need:
- SOC 2 Type II certification: $180K, 6 months
- HIPAA compliance: $240K, 8 months
- Enterprise SSO and advanced permissions: 2 engineers, 4 months
- 24/7 support infrastructure: $400K annual ongoing cost
Total upfront investment: ~$800K and 8-12 months.
Expected outcome: Win rate improvement from 18% to 35-40% in enterprise segment. Revenue impact: $2.4M additional ARR if we capture that improvement."
Why this matters: The CEO doesn't just need to know we're losing—he needs to know what it would cost to win and whether the ROI justifies it.
This turned a vague "we should invest in enterprise" recommendation into a specific capital allocation decision.
Question 3: What's Our Recommended Positioning and Why?
This is where most PMMs freeze. Making a recommendation means stakeholders might disagree. It's safer to present options and let executives decide.
But that's not strategy—that's analysis paralysis.
I made a clear recommendation:
"Recommendation: Focus on dominating mid-market ($50K-$200K ACV) and deprioritize enterprise for the next 18 months.
Rationale:
- We're already winning 61% of mid-market deals with current capabilities
- Mid-market TAM is $800M and we have <3% market share
- Enterprise requires $800K investment with uncertain payoff
- Our competitive advantage (implementation speed) matters most in mid-market
Strategic trade-off: We'll lose enterprise deals we're already losing. We'll win more mid-market deals by focusing sales and product resources."
The exec team debated this for twenty minutes. The VP Sales pushed back hard—he wanted to compete for enterprise. The CFO supported my recommendation because the ROI was clearer.
That debate was productive. We made a strategic decision: Focus on mid-market for 12 months, then revisit enterprise.
The lesson: CEOs don't need PMMs who can analyze everything—they need PMMs who can make tough recommendations and defend them.
How to Turn Competitive Intelligence Into Competitive Strategy
The mistake I made in my first CEO presentation was presenting intelligence without turning it into strategy.
Here's how I learned to make that transition:
Intelligence: "Competitor X launched Feature Y that 60% of our lost enterprise deals mentioned as a deciding factor."
Strategy: "Competitor X's Feature Y is critical for enterprise. We have three options: (1) Build it ($300K, 6 months), (2) Partner with a vendor who has it, or (3) Reposition away from enterprise. I recommend option 3 because the ROI on building Feature Y doesn't justify the investment given our current enterprise win rate."
Intelligence: "Our pricing is 30% higher than Competitor Z in the SMB segment."
Strategy: "Our pricing is 30% higher than Competitor Z. We can either (1) Lower pricing and compete on cost, or (2) Reposition to mid-market where price sensitivity is lower. I recommend option 2 because lowering pricing would compress margins by 18% while mid-market deals are 3x larger with similar win rates."
Notice the pattern: Intelligence describes what's happening. Strategy recommends what to do about it.
CEOs are drowning in intelligence. They're starving for clear recommendations.
The Presentation Structure That Actually Works for Exec Teams
After rebuilding my competitive strategy presentation, I used this structure for every CEO and exec team presentation:
Slide 1: The Strategic Question
"Where should we compete over the next 12 months: Enterprise, mid-market, or SMB?"
One slide. One question. Everything else exists to answer it.
Slide 2: Current Competitive Position
"Win rates by segment:
- Enterprise: 18%
- Mid-market: 61%
- SMB: 68%
We're winning where implementation speed matters. We're losing where enterprise compliance is required."
One slide. The current state.
Slide 3: Strategic Options
"Three options:
- Invest in enterprise capabilities ($800K, 12 months)
- Focus on mid-market and SMB where we win today
- Compete across all segments with current capabilities
We analyzed each option against revenue opportunity, investment required, and probability of success."
One slide. The choices.
Slides 4-6: Option Analysis
One slide per option showing:
- Investment required
- Expected revenue impact
- Competitive dynamics
- Risk factors
Three slides. The evaluation.
Slide 7: Recommendation
"Recommendation: Focus on mid-market for 12 months.
- Highest win rate with current capabilities (61%)
- Largest TAM opportunity with lowest investment
- Competitive advantage (speed) aligns with segment needs
- Deprioritizing enterprise means losing deals we're already losing
This decision requires:
- Sales to stop pursuing $500K+ enterprise deals
- Product to prioritize mid-market workflows over enterprise features
- Marketing to reposition messaging around mid-market buyers"
One slide. The answer.
Total: Seven slides. The entire presentation took 18 minutes. The exec team discussion took 45 minutes.
That ratio—more time debating than presenting—is what good strategy presentations create.
What CEOs Actually Want From Competitive Strategy Presentations
CEOs don't want: A comprehensive overview of what every competitor is doing.
CEOs want: Clarity on where you'll win and what you'll sacrifice to win there.
CEOs don't want: Analysis of competitive features and pricing.
CEOs want: Recommendations on which competitive battles to fight and which to avoid.
CEOs don't want: More information about the competitive landscape.
CEOs want: Decision frameworks that make capital allocation clearer.
The shift from "here's everything I know" to "here's what I recommend" is what separates PMMs who inform from PMMs who influence strategy.
How to Handle Push back on Your Strategic Recommendation
When I presented my "focus on mid-market" recommendation, our VP Sales immediately pushed back: "We've been working on a $600K enterprise deal for six months. You're saying we should walk away?"
Old me would have backed down or hedged: "Well, we should finish deals already in progress..."
New me held the position: "If we're six months into a deal with an 18% win rate, we've already invested significant sales capacity with low probability of return. My recommendation is we finish active enterprise deals but stop new enterprise prospecting. That redirects 60% of sales capacity to mid-market where win rates are 3x higher."
The CFO jumped in: "What's the revenue impact of that shift?"
I had the answer: "Based on current pipeline velocity, redirecting that capacity should add $2.4M in mid-market ARR over the next 12 months. We'll lose approximately $800K in potential enterprise ARR—deals we have an 18% chance of winning anyway."
The CEO made the decision: "Let's try it for two quarters. If mid-market performance doesn't improve as projected, we revisit."
The lesson: Strong recommendations invite pushback. That's good. Pushback means people are engaging with the strategy, not just nodding politely.
Your job isn't to avoid pushback—it's to defend your recommendation with data and be willing to adjust if someone raises a valid point you missed.
What works: "That's a fair point. Here's why I still believe this is the right path, and here's what would change my recommendation."
What doesn't work: Immediately backing down or getting defensive.
The executives who pushed back hardest on my recommendations became the strongest supporters after I demonstrated I'd thought through their objections.
The Uncomfortable Part of Competitive Strategy (Choosing What You Won't Win)
The hardest part of presenting competitive strategy to CEOs isn't describing opportunities—it's recommending what you'll sacrifice.
Strategy is about choice. Every "yes" to one segment or positioning is a "no" to something else.
When I recommended focusing on mid-market, I had to explicitly say: "This means we stop competing for enterprise deals. We will lose opportunities. Sales will be frustrated. Some prospects will tell us we're not 'enterprise-ready' and we'll agree with them."
That felt risky. Executives hate hearing about opportunities we're walking away from.
But the CEO appreciated the clarity: "I'd rather dominate mid-market than lose 82% of enterprise deals while spreading ourselves thin. At least now we have a clear positioning."
The competitive strategies that fail are the ones that try to win everywhere. You end up mediocre in every segment instead of dominant in one.
The competitive strategies that work are the ones that explicitly choose where to win and accept the losses that come with that choice.
Most PMMs are afraid to make that recommendation. They hedge: "We should focus on mid-market while also building enterprise capabilities..."
That's not strategy. That's trying to avoid making a choice.
CEOs respect PMMs who make clear recommendations and acknowledge the trade-offs.
How to Build a Competitive Strategy Recommendation (The Real Work)
The presentation is the easy part. The hard work is building a recommendation you can defend.
Here's what I did before my second CEO presentation:
I analyzed 60 competitive deals: 30 wins, 30 losses. I looked for patterns in deal size, buyer persona, competitive threats, and win/loss factors.
I interviewed 10 sales reps: What deals are they most confident closing? Where do they struggle? What objections do they can't overcome?
I modeled the revenue impact: If we focus on mid-market, what's the realistic revenue upside? If we invest in enterprise, what's the probable improvement in win rates and what does that mean for ARR?
I pressure-tested my recommendation: I showed it to our VP Product and VP Sales before the CEO presentation. They poked holes in it. I refined it.
This took two weeks of actual work. The seven-slide presentation took two hours to build.
The mistake most PMMs make: Spending 90% of time on slides and 10% on analysis.
What actually works: Spending 90% of time on analysis and 10% on slides.
If your analysis is solid and your recommendation is defensible, the slides are easy. If your analysis is weak, no amount of slide polish will save you.
What Good Competitive Strategy Presentations Accomplish
Bad competitive strategy presentations: Inform executives about the competitive landscape. They nod, say "interesting," and nothing changes.
Good competitive strategy presentations: Force a strategic decision. They debate your recommendation, challenge your assumptions, and ultimately make a choice about where to compete.
The CEO presentation where I fumbled through competitive analysis? Nothing changed. We kept competing everywhere and winning nowhere specific.
The CEO presentation where I recommended focusing on mid-market? Within 30 days:
- Sales territories were redrawn to focus on mid-market accounts
- Product roadmap was reprioritized around mid-market workflows
- Marketing messaging was updated to target mid-market buyers
That's the difference. One presentation informed. One presentation drove strategic change.
The measure of a good competitive strategy presentation isn't how well it's received—it's whether it results in a clear strategic choice and resource reallocation.
The Follow-Up That Matters More Than the Presentation
Two weeks after my competitive strategy presentation, the CEO asked me to join the board meeting to present the competitive strategy we'd decided on.
I didn't present the same deck. I presented the decision we'd made and the early results.
"We decided to focus on mid-market and deprioritize enterprise. Two weeks in:
- Sales has shifted 65% of prospecting to mid-market accounts
- Pipeline in mid-market segment up 22%
- Product has reprioritized roadmap to address top 3 mid-market workflow requests
- Marketing updated messaging to focus on mid-market buyer needs
We'll measure success by mid-market win rate improvement and pipeline velocity over the next two quarters."
That's what turned a presentation into lasting credibility. I made a recommendation. The exec team made a decision. I reported on execution and early results.
Most PMMs present strategy and then disappear. They don't follow up. They don't track whether the strategy is being executed. They don't measure whether the recommendation was correct.
The PMMs who become strategic advisors to CEOs: Make recommendations, track execution, measure outcomes, and report back on whether the strategy is working.
That's how you go from "the person who knows about competitors" to "the person who shapes where we compete."
The CEO doesn't need another analyst. He needs someone who can make the hard strategic choices clearer and then track whether those choices were right.
That's what competitive strategy presentations are actually for.