Closed Won

🦙 Getting Past Gatekeepers

Brian LaManna

February 15, 2026

Read Time: 4 minutes

Anthropic hits $14 billion revenue run rate, becomes fastest-growing software company ever.
And they are about to grow a lot faster
They just got a $30BN funding round valuing them at $380BN.
By the numbers…

NEWS TO KNOW

📚 – What’s happening to software companies – explained
📝 – Trying to disqualify candidates
💸 – Breaking the 4th wall

BEST FROM LAST WEEK

Getting Past Gatekeepers

Ever feel like gatekeepers are professional brick walls designed to stop you from reaching decision makers?

You’re not wrong.

But here’s the thing: they’re just doing their job, and once you understand their world, getting past them becomes a lot easier.

Most sales reps mess this up by either being too aggressive or sharing way too much information upfront.

The secret?

Work with gatekeepers, not against them, using a systematic approach that gives you multiple chances to succeed.

The 4 Core Principles

1. Information is currency – spend it wisely

Share details only when directly asked, and even then, keep it minimal.

Think of it like a poker game where showing your hand too early kills your chances.

The gatekeeper doesn’t need your life story; they need just enough to make a decision.

Example: Instead of “Hi, this is Sarah from TechSolutions calling about our new AI-powered customer service platform that can reduce response times by 40%,”

Try: “Hi, could you connect me with David? It’s Sarah.”

2. Questions are your steering wheel

The person asking questions controls the conversation.

When they push back with questions, answer briefly and redirect with your own question.

This keeps momentum moving toward your goal.

Example: GK: “What’s this regarding?” You: “It’s about the Q4 planning session. Is he in a meeting now?”

3. Use the 1-2 Punch System

You get ~2 legitimate attempts to get through.

Your odds dramatically lower beyond your second attempt… you can still try but don’t expect much in a short timeframe.

4. Context beats company names

Instead of leading with your company name (which triggers their “sales call” alarm), reference something specific and relevant to their business.

This makes you sound like an insider, not an outsider.

Example: “It’s about the Dallas expansion project” vs “I’m calling from ABC Consulting.”

The Round 1, Round 2 Punch

First Attempt: The Confidence Play

Script: “Hi, could you put me through to Jennifer? This is Mike.”

Why it works: You sound like someone who belongs. No company name, no explanation, just confidence. Use first names only – full names trigger suspicion.

When it fails: Sharp gatekeepers will ask “What company are you with?” or “What’s this regarding?”

Success rate: About 30% of gatekeepers will put you through immediately.

Second Attempt: The Context Drop

Script: “It’s about the investor presentation for the Seattle launch. Could you let her know it’s Mike from DataFlow calling?”

or

“It’s regarding the compliance audit timeline. Could you tell him Mike from RegTech Solutions is on the line?”

Why it works: You’re referencing something specific that sounds internal and important. You’re not selling; you’re following up on business matters.

Pro tip: Research recent company announcements, press releases, or industry events they’re involved in. LinkedIn company pages are goldmines for this intel.

When it fails: The most experienced gatekeepers will still push for more details about what you actually do.

What NOT to Do

  • Never lie about being a current vendor or having met them before
  • Don’t name-drop unless you have permission
  • Avoid saying “This will only take a minute” (huge red flag)
  • Don’t ask “Is now a good time?” (of course it’s not)
  • Never argue with or belittle the gatekeeper
  • Don’t leave voicemails saying “Please have them call me back” without context

The Psychology Behind Why This Works

Gatekeepers are trained to filter out obvious sales calls, but they’re also terrified of blocking important business communications.

By positioning yourself as someone dealing with business matters rather than trying to sell something, you tap into their fear of making a mistake.

The Bottom Line

Gatekeepers aren’t your enemy.

They’re overworked people trying to protect their boss’s time while not missing anything important.

Respect their position, work within their framework, and use strategic approaches that match the situation and their responses.



Coming back from an insane week at Gong SKO in Cancun, Mexico.

Feeling an extra level of gratitude right now.

More news on that soon…

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