Chapter 2: Intelligence as Insight
The biggest lie in sales is “The right time to call is now.”
In a greenfield sale, that might be true. If a potential customer has no CRM, they need one today. But in a displacement sale, timing is physics. You cannot displace a competitor who just signed a three-year contract yesterday. You cannot displace a database that is currently processing Black Friday traffic.
To win a displacement deal, you must find the Window of Opportunity.
Most salespeople treat intelligence gathering like checking a box. They look at the company’s “About Us” page, they check the stock price, and they make the call. This is why they fail.
Displacement requires Deep Context. You need to know more about the incumbent’s friction points than the customer does.
[!IMPORTANT] Discovery is a Loop, Not a Stage. John Care reminds us that the best intelligence isn’t gathered in a conference room; it’s gathered during the pilot. Every log entry, every configuration hurdle, and every coffee with an engineer is an opportunity to discover the next “Root.”
The 90-Day Decision Zone - Using Inertia Against Itself
Every contract has a heartbeat. It starts strong, it plateaus, and then, roughly 90 days before renewal, it becomes malleable.
We call this the Decision Zone.
If you call 12 months before renewal, you are a nuisance. The CIO isn’t going to rip out their infrastructure when they still have a year of prepaid credits. If you call 30 days before renewal, you are too late. The paperwork for the renewal is already being drafted by legal.
But at 90 days? At 90 days, the CIO is staring at a 20% price hike from the incumbent. They are remembering the three outages they had last quarter. They are looking for leverage.
Your first job is not to sell. It is to build a calendar.
- Which of your target accounts renews in Q3?
- When did they implementation start? (Add 3 years to that date).
- Technographic Triggers: Tools like BuiltWith or HG Insights aren’t just for list building; they are for timing. If a company installed Incumbent X in January 2023, you know exactly when to call in 2026.
Business Signals: The “Why Now”
Timing isn’t just about dates; it’s about chaos.
Incumbents thrive on stability. They lose when the environment changes faster than they can adapt. You are looking for three specific types of chaos:
1. The Post-M&A Indigestion
When Company A buys Company B, they inherit a mess. Company A uses AWS; Company B uses Azure. Company A uses Salesforce; Company B uses HubSpot. For the next 18 months, there is no “standard.” There is only friction. This is the perfect wedge. You don’t pitch a total migration; you pitch the “Unifying Layer.” You pitch the solution that helps them make sense of the mess.
2. The new “Sheriff”
Watch the C-Suite. When a new CIO or CTO is hired, the clock resets. The old CTO built their career on the Incumbent. The new CTO was hired to “fix things.” They have no loyalty to the legacy stack. In fact, ripping it out is the fastest way to prove they are transformative. A new executive hire is the single strongest signal that an account is ready to be displaced.
3. The 10-K Confessional
Public companies tell you exactly what hurts in their 10-K filings, but salespeople rarely read them. Look for the “Risk Factors” section. Are they complaining about “margin compression”? That’s a TCO pitch. Are they worried about “cybersecurity threats”? That’s a security/governance pitch. If the CEO tells Wall Street they need to cut costs by 15%, and you pitch a “premium solution,” you deserve to lose.
Workforce Intelligence (The Ghost in the Machine)
Sometimes, the loudest signal comes from the people who aren’t there.
Go to the careers page of your target account. What are they hiring for?
- “Senior Cobol Engineer”? They are trapped in legacy hell.
- “Cloud Security Architect (Urgent)”? They just had a breach or failed an audit.
- “FinOps Analyst”? Their cloud bill is out of control.
We once helped a challenger displace a major database vendor simply by monitoring LinkedIn. We noticed that three senior database administrators left the target company in the same month. We didn’t know why, but we knew the “Brain Drain” had happened. The challenger called the CIO the next week: “I noticed your database team is in transition. We can manage that workload for you.” They got the meeting.
The AE’s Intel Toolkit: Reading the Field Signals
You don’t need a private eye to find high-context intel. You just need to know where to look.
| Signal Type | Where to Look | What it Means |
|---|---|---|
| The Skills Gap | LinkedIn Job Posts | If they are hiring for “COBOL” or “Legacy Java” specialists, they are desperate to keep the lights on. |
| The Friction Point | Glassdoor Reviews | Search for engineering reviews mentioning “Outdated tools” or “Technical debt.” This is the internal “Change Champion” shouting for help. |
| The Renewal Window | Public Filings (10-K) | Look for “Commitment Obligations” or “Future Spend.” They tell you exactly when the big contracts expire. |
| The Strategic Shift | CIO Interviews / Podcasts | If the CIO is talking about “AI Transformation” but the incumbent doesn’t support it, you have your wedge. |
The Review Mine
Finally, listen to the users. Go to G2, Capterra, or even Reddit (r/sysadmin). Search for the incumbent. Don’t look for the 5-star reviews. Look for the 3-star reviews. The 1-star reviews are just angry. The 3-star reviews are specific. “Great uptime, but the reporting module takes 4 hours to load.” “Good support, but the API documentation is outdated.”
Take that specific complaint. Put it in your email subject line. “Is your reporting module taking 4 hours to load?”
It looks like magic. It’s just intelligence.