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WHO'S FLYING NOW?
The pilot program was flawless. Right up until the moment it wasn't.
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Your Pilot Is Working. That's When It Dies.
73% of successful AI pilots die before they scale. The technology works. The ROI is proven. But somewhere between week 5 and month 6, momentum evaporates.
The killers are always the same: risks you haven't named yet, and a CEO whose attention is already shifting.
What Actually Kills Pilots
Think of momentum as physics: mass times velocity. You've built velocity through your pilot. Scaling means adding mass (more users, more complexity, more organizational surface area) without losing speed.
73% of pilots lose that speed between week 5 and month 6. A risk surfaces that nobody planned for, or executive commitment quietly evaporates, and suddenly your pilot is stuck in bureaucratic purgatory.
The founders who break through have one early conversation that transforms their CEO from a passive sponsor to an active protector.
A Series B SaaS company built AI-powered customer success scoring. Week 8, they started scaling. Week 12, a customer filed a GDPR complaint. Nobody had documented what data the AI was processing. The entire initiative froze while legal, privacy, and engineering fought over remediation.
By week 5, four risk categories are already forming. Most founders don't see them because they're focused on adoption and metrics. But these risks compound quietly, and by the time they surface, your momentum is gone.
Category 1: Regulatory Landmines. Your pilot processes data and influences decisions. Somewhere in that flow, regulatory requirements apply: GDPR, CCPA, industry-specific mandates, accessibility standards. The danger isn't that compliance matters—it's that you're operating without knowing where the boundaries are.
The question to ask now: "If we scale to 10x users tomorrow, what compliance requirement would we trigger that we're not ready for?"
Category 2: Ethical Fault Lines. AI systems inherit bias from their training data and amplify human decision patterns. If you haven't defined ethical guardrails, you're building technical debt that becomes reputational exposure.
The question to ask now: "What's the worst decision our AI could make, and what framework would catch it before it reaches a customer?"
Category 3: Operational Fragility. What breaks when you go from 50 to 500 users? Not just infrastructure: processes, support capacity, decision rights, escalation paths.
The question to ask now: "What's the single point of failure that would take down our pilot, and how quickly could we recover?"
Category 4: Reputational Scenarios. Your AI will eventually do something unexpected. A customer will share a screenshot. A competitor will raise questions. Your board will ask why nobody anticipated this.
The question to ask now: "If a skeptical journalist asked us to explain how this works and what could go wrong, could we answer with confidence?"
The 30-Minute Risk Audit
Block 30 minutes with your pilot lead this week. Go through the four questions above. For each risk you can't answer clearly, create a one-line mitigation plan: risk identified, owner assigned, next step defined, timeline committed.
It's about naming what you're carrying so it doesn't surprise you later.
CEO Commitment (The Momentum Insurance Policy)
Your pilot's most significant risk isn't technical anymore. It's your CEO's attention span.
Here's the pattern: Week 5, the pilot is working. Week 8, a blocker surfaces. Week 10, you're waiting for someone with authority to clear it. Week 12, your CEO is surprised the pilot has stalled. By week 16, momentum is dead.
The technology didn't fail. Your CEO's attention moved to something louder, and your pilot got stuck in organizational purgatory.
Active protection requires three specific commitments from your CEO:
1. Public Visibility That Creates Consequences. Your CEO needs to make this pilot visible in a way that changes organizational behavior. A specific, public statement about what this pilot means for company strategy and what success looks like. When people know the CEO is watching, resistance patterns shift.
Ask: "Will you make a specific statement to the organization about this pilot's strategic importance in next week's all-hands?"
2. Direct Escalation Authority. Your pilot will hit blockers: legal reviews that stretch for weeks, budget questions that resurface, stakeholder conflicts that spiral. You need explicit authority to escalate obstacles directly to your CEO, with the expectation of rapid resolution.
Ask: "When we hit blockers, can I escalate directly to you with an expectation of resolution within 48 hours?"
3. Resource Protection Through Scale. The moment your pilot shows promise, other initiatives will try to borrow your resources. Without explicit protection, your pilot gets resource-starved just as it's ready to scale.
Ask: "Will you commit to protecting this pilot's team and budget through the next quarter, so we're not defending resources while trying to prove production readiness?"
These aren't abstract commitments. They're concrete, actionable, and measurable. Most CEOs will agree conceptually. The difference is making them specific enough that there's accountability for follow-through.
The Conversation Framework
Book 30 minutes this week. Use this structure:
Opening: The Momentum Reality
Present where you are: specific metrics, specific wins. Frame the inflection point: pilots either accelerate into production or stall due to organizational friction.
The Risk You've Named
Share your risk audit. Four categories will surface as we scale. None is fatal if addressed early. All are fatal if they compound.
The Ask: Three Concrete Commitments
Request public visibility, escalation authority, and resource protection. Be specific about what each means in practice.
Close: The Decision Frame
You're requesting active protection for 90 days. If you hit milestones, you've earned production investment. If you don't, kill it fast. The biggest risk isn't technology—it's organizational friction you can't clear without CEO involvement.
These aren't abstract commitments. They're concrete and measurable. Most CEOs will agree conceptually. The difference is making them specific enough that there's accountability for follow-through.
The Week 5 Window
Week 5 is when this work matters. Earlier, you didn't have proof points. Later, you're already fighting obstacles instead of preventing them.
Risk compounds faster than pilots scale. Executive attention drifts to whatever's loudest. This week determines which path you're on.
Run the 30-minute risk audit. Have the CEO conversation. Transform sponsorship into protection before friction emerges.
The 27% of pilots that reach production do this work in week 5. The 73% that die wait until they're already stuck.
Block 60 minutes this week. 30 for the risk audit. 30 for your CEO.
Everything else can wait.Dale Zwizinski, Editor of Revenue Creator, and Chief GTM Officer at Revenue Reimagined.
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Vet Your Data Quality. The #1 warning: some platforms use inaccurate third-party data. Clean, validated data is the real secret to booking meetings, not just sending spam.
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Match Tool to Your Motion. The "best" tool depends entirely on your team. Your specific ICP (e.g., inbound-heavy) will decide if you need Apollo, Clay, or Gong.
Test the Rep Workflow. A tool should be fast. One team added Salesloft just because HubSpot's sequencing tasks "involved a lot of clicks" and slowed them down.
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