I'd been a product marketer for three years before I proposed my first positioning change to our CEO.
The data was clear: Our positioning as an "AI-powered analytics platform" wasn't resonating. Win/loss interviews showed buyers cared about "time to insight" not "AI capabilities." Our close rate was 32% when we led with AI, 54% when reps ignored the positioning and focused on speed.
I had the data. I had the recommended repositioning. I was confident.
The CEO listened to my 15-minute presentation, asked three questions, and then said: "I appreciate the analysis, but I'm not convinced we should change positioning. AI is our technical differentiation and our main product investment focus. Changing positioning would confuse the market and undermine our product strategy."
My recommendation was rejected.
Looking back, I realize my mistake: I presented repositioning as a marketing decision when it's actually a strategic business decision that affects product, sales, hiring, and market perception.
Six months later, I proposed another repositioning—this time with a completely different approach. The CEO approved it in one meeting, and within 90 days, win rates improved from 35% to 51%.
The difference: I learned how to present repositioning as strategic business change, not just messaging adjustment.
Why Positioning Changes Are Different From Other Marketing Decisions
Early in my career, I thought: Positioning is marketing. PMM owns it. I should be able to propose changes and get them approved like any other marketing initiative.
What I learned: Positioning is company strategy. Changing positioning affects:
- Product roadmap: Features prioritized based on what positioning emphasizes
- Sales strategy: Which buyers to target and how to sell to them
- Hiring: What capabilities and roles to prioritize
- Market perception: How analysts, investors, and buyers see you
- Competitive strategy: Where you compete and where you avoid competition
CEOs resist positioning changes because changing positioning is expensive and risky.
Expensive: Sales needs retraining, marketing materials need updating, analyst relationships need resetting, customer messaging needs revising.
Risky: Get it wrong and you confuse the market, lose deals, and waste months recovering.
That's why presenting repositioning to CEOs requires more than showing data—it requires demonstrating you've thought through business implications and de-risked the change.
The Mistake I Made in My First Repositioning Presentation
What I presented:
"Based on 40 win/loss interviews, buyers care about implementation speed more than AI capabilities. Our positioning should emphasize 'operational in 2 weeks' instead of 'AI-powered analytics.' Here's the data, here's the new positioning, here's the messaging framework."
Why it failed:
I presented repositioning as a messaging change. I showed what we should say differently, but I didn't address:
- How this aligns with product strategy
- What happens to our 18-month AI product investment
- How we'll manage market perception shift
- What competitors will do in response
- What could go wrong and how we'd mitigate it
CEO's response captured it: "You're proposing we abandon our core differentiation based on 40 interviews. What if those interviews aren't representative? What if we've just done a poor job communicating our AI value?"
He wasn't wrong. I hadn't de-risked the recommendation or shown how repositioning aligned with broader strategy.
The Framework That Got My Second Repositioning Approved
Six months later, I proposed repositioning from "developer tool" to "operations platform."
This time, I used a completely different framework:
Section 1: The Strategic Problem (Not Just the Data)
Old approach: "Here's 40 interviews showing buyers care about X not Y."
New approach: "We're losing 67% of deals to competitors who position on workflow automation while we position on developer capabilities. This positioning mismatch is costing us $4.2M annually in winnable pipeline."
The difference: I framed it as a strategic business problem (we're losing deals and revenue) not a marketing problem (our messaging isn't working).
CEO's reaction: "If repositioning solves a $4.2M revenue problem, I'm interested. Show me the case."
Section 2: Customer Validation (With Risk Mitigation)
Old approach: "40 interviews show buyers care about X."
New approach: "We validated new positioning with 60 customers and prospects across three segments:
Existing customers (20 interviews):
- 75% said new positioning better describes why they bought
- 15% concerned new positioning strays from our roots (mitigated by emphasizing we're not removing developer capabilities, just leading with operations benefits)
- 10% neutral
Won deals (20 interviews):
- 85% said new positioning would have accelerated their decision
- "We bought you for operations workflow, not developer tools—we almost didn't evaluate you because we're not a dev-tools buyer"
Lost deals (20 interviews):
- 70% said new positioning addresses why they didn't buy
- "You positioned as dev tool, we needed operations solution"
Risk mitigation: To avoid alienating developer segment (20% of revenue), we're maintaining developer messaging as secondary positioning, leading with operations for 80% of target market."
The difference: I showed customer validation AND addressed the "what if you're wrong" concern by quantifying risk and showing mitigation.
CEO's reaction: "If 85% of won deals say this positioning would have accelerated decisions, that's compelling. And I appreciate you thought through the developer segment risk."
Section 3: Competitive Implications (Not Just Buyer Research)
Old approach: "Buyers care about operations workflow."
New approach: "Competitive analysis of new positioning:
Current positioning (Developer Tool):
- We compete with Competitor X, Y, Z
- Market is crowded, differentiation unclear
- Win rate: 34%
New positioning (Operations Platform):
- We avoid Competitor X, Y entirely (they're dev-focused)
- We compete with Competitor A, B (operations-focused)
- Our win rate vs. A and B: 62% (based on deals where we positioned this way)
- Market opportunity: $120M TAM (operations) vs. $45M TAM (developer tools)
Strategic implication: Repositioning expands our TAM by 2.7x and improves win rate by 28 points in target segment."
The difference: I showed how repositioning changes competitive dynamics and explained why that's strategically advantageous.
CEO's reaction: "So we're repositioning to compete in a larger market where we already win at higher rates. That's not just messaging—that's strategy."
Section 4: Implementation Plan (With Timeline and Resources)
Old approach: "Here's the new messaging framework. Marketing will update materials."
New approach: "90-day implementation plan:
Phase 1 (Weeks 1-4): Validation & Pilot
- Test positioning with next 20 deals (10 operations-focused, 10 developer-focused)
- Measure: Does operations positioning improve close rate in target segment?
- Gate: Must see 40%+ improvement in operations segment to proceed
Phase 2 (Weeks 5-8): Sales Enablement & Collateral
- Retrain sales on new positioning (3 workshops)
- Update pitch decks, battlecards, demo scripts
- Create customer case studies highlighting operations outcomes
- Investment: $25K (design, content, sales workshops)
Phase 3 (Weeks 9-12): Market Launch
- Update website, product messaging, analyst briefings
- Launch customer campaign highlighting operations use cases
- Monitor: Win rate, pipeline quality, customer sentiment
Total investment: $40K + 120 hours PMM time Expected ROI: $4.2M annual revenue recovery, payback in 3 weeks
What could go wrong:
- Developer segment feels alienated (mitigation: maintain secondary positioning)
- Sales team resists change (mitigation: pilot program shows results first)
- Market confusion during transition (mitigation: phased rollout with customer communication)
Decision needed: Approve pilot phase (weeks 1-4) to validate positioning. If metrics support it, proceed with full implementation."
The difference: I presented repositioning as a phased, de-risked business initiative with clear gates, not a "flip the switch" marketing change.
CEO's reaction: "Let's do the pilot. If the metrics support it, we'll go all-in."
What Made the Second Presentation Work (The Real Difference)
The first presentation: "Here's customer data showing we should change messaging."
The second presentation: "Here's a strategic business case for repositioning that:
- Solves a $4.2M revenue problem
- Is validated by 60 customer interviews
- Expands our TAM and improves competitive win rates
- Has phased implementation with validation gates
- Addresses risks and shows mitigation"
The CEO later told me: "The first time, you asked me to trust 40 interviews and change our positioning. The second time, you showed me a de-risked business plan with strategic upside. Easy decision."
The Five Questions CEOs Ask About Positioning Changes (And How to Answer Them)
Question 1: "How do you know this isn't just a messaging execution problem?"
What they're really asking: "Are we sure our positioning is wrong, or did we just communicate it poorly?"
How to answer: "Fair question. I tested both—we had reps use existing positioning but with better messaging. Win rate stayed at 34%. When same reps used new positioning, win rate jumped to 54%. The positioning itself is the problem, not how we communicate it."
Question 2: "What happens to our product strategy if we reposition?"
What they're really asking: "Does this undermine our product roadmap?"
How to answer: "New positioning aligns with where Product is already heading—70% of roadmap addresses operations workflows. We're not changing product strategy—we're positioning around what we're already building instead of what we used to be."
Question 3: "Won't this confuse existing customers?"
What they're really asking: "What's the churn risk?"
How to answer: "I interviewed 20 existing customers. 75% said new positioning better describes why they bought—they already use us for operations workflows. 15% concerned we're abandoning developer features. We're mitigating by emphasizing we're not removing capabilities, just leading with operations benefits. Expected churn impact: <1%."
Question 4: "What do competitors do when we reposition?"
What they're really asking: "What's the competitive risk?"
How to answer: "Current positioning has us competing with Competitor X, Y—crowded market, unclear differentiation. New positioning avoids them entirely—we'll compete with Competitor A, B in operations space where we already win 62% of deals. Competitors A and B are smaller and less well-funded. This is strategically advantageous repositioning."
Question 5: "How do we measure if this worked?"
What they're really asking: "How will we know if we made the right call?"
How to answer: "Three metrics over 90 days:
- Win rate in target segment: Should improve from 34% to 45%+ (50% improvement)
- Pipeline quality: Should see larger deals from operations buyers ($200K+ vs. current $140K)
- Sales cycle: Should shorten from 5.2 to 4 months as positioning clarifies fit earlier
If we don't see 40% improvement in win rate by day 60, we reassess."
The Presentation Structure That Works
Total: 7 slides, 20 minutes of presentation, 30+ minutes of discussion.
Slide 1: The Strategic Problem
"We're losing $4.2M annually in winnable pipeline because our positioning (developer tool) doesn't match what buyers need (operations solution). This positioning mismatch is costing us deals we should win."
Slide 2: Customer Validation
"60 customer interviews across existing customers, won deals, and lost deals validate new positioning addresses this problem. 75-85% positive response across all segments."
Slide 3: Competitive Strategy Shift
"Repositioning moves us from crowded developer tool market (win rate 34%) to operations platform market where we already win 62% of deals. TAM expands 2.7x."
Slide 4: What Changes
"Primary messaging shifts from 'developer productivity' to 'operations automation.' Product roadmap unchanged—we're positioning around where we're already investing, not changing direction."
Slide 5: Implementation Plan
"90-day phased rollout: Pilot (validate metrics), Enablement (train sales), Launch (update market positioning). Investment: $40K."
Slide 6: Risk Mitigation
"Three risks and mitigations:
- Developer segment alienation → maintain secondary positioning
- Sales resistance → pilot shows results first
- Market confusion → phased rollout with customer communication"
Slide 7: Decision & Metrics
"Approval needed for pilot phase. Success metrics: 40% win rate improvement in 60 days. If validated, proceed with full rollout."
The Follow-Through That Determines Success
Getting CEO approval for repositioning is step one. Executing it and proving it worked is what builds lasting credibility.
After my repositioning was approved, I sent weekly updates:
Week 4 (End of Pilot): "Pilot results: Win rate in operations segment improved from 34% to 52% across 12 test deals. Validated hypothesis. Recommend proceeding to Phase 2."
Week 8 (End of Enablement): "Sales enablement complete: 85% of reps trained on new positioning. Early adoption at 68% based on call recordings. Win rate holding at 51%."
Week 12 (End of Launch): "Repositioning complete. Win rate improved from 34% to 51% (+17 points). Average deal size increased from $140K to $185K. Sales cycle decreased from 5.2 to 4.4 months. ROI: $3.8M annual revenue impact from $40K investment. 95x return."
That follow-through did more to build CEO trust than the original presentation.
CEOs remember whether you delivered on repositioning promises more than they remember your presentation.
The Uncomfortable Truth About Proposing Positioning Changes
Most PMMs think: If the data supports repositioning, CEOs should approve it.
The reality: CEOs approve repositioning when:
- The business case is compelling (revenue impact, competitive advantage)
- Customer validation is substantial (not just a few interviews)
- Risks are identified and mitigated
- Implementation is phased and de-risked
- Success metrics are clear
- PMM has credibility to execute
The PMMs who successfully get repositioning approved:
- Frame it as strategic business change, not marketing change
- Show customer validation across multiple segments
- Address competitive implications
- Present phased implementation with validation gates
- Prove it worked through follow-through
The PMMs whose repositioning proposals get rejected:
- Present it as messaging change
- Rely on limited customer research
- Ignore product and competitive implications
- Propose "flip the switch" implementation
- Don't follow through or measure impact
The difference in career trajectory is dramatic. PMMs who can successfully reposition companies become strategic leaders. PMMs who can't stay at tactical execution levels.
Proposing repositioning is one of the highest-leverage strategic moves a PMM can make. Get it right, and you reshape company direction. Get it wrong, and you lose credibility.
The key isn't having perfect data—it's presenting repositioning as a de-risked strategic business opportunity that CEOs can't ignore.
Master that, and you'll go from suggesting messaging changes to driving company strategy.
That's when your career accelerates.