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💼 big deal tactics
What not to do in your next CXO meeting
Daily Sales Newsletter October 17, 2025 |
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Gal Aga: The fast way to lose an executive’s attention
Nate Nasralla: Make champions your inside sellers
Jamal Reimer: Make the problem matter before you sell
Matthew Codd: He was literally burning pipeline
The fast way to lose an executive’s attention
Gal Aga breaks down why most exec-level sales calls fail, and how top reps win by leading with insight, not intros.
Don’t treat exec calls like regular demos
Too many AEs walk into senior meetings with the wrong playbook.
➤ Executives aren’t there to hear a feature walkthrough
➤ They’re not impressed by logos, awards, or endless questions
➤ They want clarity on strategic impact, not product mechanics
1. Lead with insight, not discovery
If you start with “Tell me about your challenges,” you’ve already lost.
Great exec calls begin with:
✔ Market trends the buyer may not have considered
✔ Peer benchmarks and executive viewpoints
✔ A recap of what you’ve already heard from their team
Sample opener:
“I’ve spent time with your team around [problem]. Can I kick off with a few patterns we’re seeing and how they map to your org?”
Anchor insights with proof, then pivot:
“How does this align with what you’re seeing?”
2. Focus on the 3 Why’s
Execs care about why something matters. Your product comes second.
✔ Why do anything?
→ What risk are they sitting on?
✔ Why now?
→ What’s the cost of waiting?
✔ Why you?
→ Back your pitch with examples, proof points, and a brief walk-through
Leave the deep product details for their team. Speak to outcomes, not workflows.
3. Always sync with your champion first
Never walk into an exec call blind.
Your champion can brief you on:
➤ Who the exec is
➤ How involved they’ve been
➤ What they’re skeptical of
➤ What they expect from this call
Use that prep to tailor the conversation and build a sharper story.
Bonus tip:
Build an executive summary with your champion and send it ahead of the call. Even if it’s not read, you’ll be better positioned than 99% of reps.
What great AEs do differently
✔ Bring insight, not intro slides
✔ Stay at the Why-level conversation
✔ Prep with the internal champion before every exec meeting
✔ Use brief, visual proof to validate points—not product demos
Make champions your inside sellers
Nate Nasralla reveals how top sellers drive complex deals forward by making their message travel, enabling champions, and staying inside power conversations.
Speak how executives think
Big deals don’t close because of features. They close because the message clicks.
➤ Executives buy the story, then justify it with ROI
➤ Champions carry simple, clear soundbites - not slide decks
➤ If your message isn’t repeatable, it dies
To make your message stick:
✔ Use internal language, metrics, and nicknames
✔ Tie it to a shift they’re already experiencing
✔ Boil the entire story down to two sentences
Structure it like this:
→ Something’s changing
→ Most respond with X
→ That leads to cost/consequence
→ A different response unlocks better outcomes
If your message can’t travel through the org, you won’t either.
Turn champions into insiders
Stop presenting to champions. Start building with them.
✔ Co-create the internal pitch they’ll deliver
✔ Give them short, forwardable messages
✔ Help them lead internal conversations, not follow them
Strong champions:
→ Know the politics
→ Push back when needed
→ Can get people to move
The win comes from their internal influence, not your external pitch.
Multi-threading starts with message clarity
Your best reps are only present for a fraction of the deal conversations.
✔ Use exec-to-exec intros and LinkedIn to get messages passed along
✔ Keep it under 100 words, sharp and skimmable
✔ No branding - use their voice, their terms
If you’re not in the room, make sure your message is.
Use discovery to write the story
Good discovery doesn’t stop at surface pain.
Go deeper with:
→ Reach – Who else feels this?
→ Frequency – How often does it happen?
→ Severity – What’s the impact?
Stack "which means..." questions to go one level deeper every time. That’s how you find the core storyline the buyer will actually repeat.
Build the business case with your buyer, not for them
Don’t present a case. Build one together, in their words.
✔ Use their logo, their data, their timeline
✔ Start early and evolve it over time
✔ Ask champions to bring in Ops, IT, and Finance
The business case should feel like their slide, not your proposal.
Executive priorities right now (Q4 2025)
➤ Consolidation – Fewer tools, tighter stacks
➤ Resilience – Can we adapt faster than the market?
➤ Optionality – Don’t lock us in, give us leverage
Anchor your pitch to one of these or risk being ignored.
Make the problem matter before you sell
Jamal Reimer explains how most sellers fail by pitching too soon, before making the buyer care about the problem.
Pitch the problem before the product
Most sellers rush into the pitch assuming the buyer already agrees that the problem is worth solving.
Here’s the usual script:
✔ "You care about X"
✔ "We help you get X using our product"
✔ "We’re the best at doing X"
✔ "Here’s a customer who got X with us"
But if the buyer isn’t sold on the urgency of X, the pitch goes nowhere.
⇢ Especially true with enterprise buyers juggling multiple priorities
Make your problem the priority
Take a CISO, for example. You’re selling fraud detection. But they also care about:
➤ Intrusion protection
➤ Social engineering
➤ Physical access risks
➤ Compliance audits
➤ Secure code
Why should your solution to fraud get attention over these?
Your job: elevate the problem.
Get them to say, “This needs fixing. Now.”
The best deck doesn’t pitch the product
Zuora nailed this using Andy Raskin’s now-famous sales deck structure:
✔ No product at the beginning
✔ No long feature list
✔ No “we’re better” claims
Instead, it built belief around the problem: thriving in a subscription economy.
It worked because it told a compelling story that framed their solution as essential.
Follow this 6-part narrative
This structure gets executive attention and unlocks bigger deals:
Name a big, relevant shift
→ “The world is changing fast, and this shift is affecting everyone.”Show there’ll be winners and losers
→ “Some will adapt. Others will fall behind.”Reveal the common thread
→ “Here’s what all the winners have in common…”Tease the promised land
→ “This is what success looks like after the change.”Position features as ‘magic gifts’
→ “Here’s what you’ll need to get there…”Prove it works
→ “Other companies are already winning with this approach.”
Use this framework to tell your story, not just your product’s specs.
Why it works for large, complex deals
✔ Gets executive-level attention
✔ Builds urgency without pressure
✔ Positions your solution as strategic, not tactical
And most importantly: it makes your buyer care before you ever ask them to buy.
TO-GO
Aaron Reeves: How to break into large accounts in 2025
Mark Hunter: The secret of closing bigger deals faster
Troy Munson: How I broke into large enterprise companies
Matthew Codd: He was literally burning pipeline
Recommended tools*
Mailshake: Cold email made simple and effective
Smartlead: Automate outreach without losing the human touch
folk: Manage relationships and scale outreach in one smart CRM
Systeme.io: All-in-one platform to launch and sell your products
Check them out!
QUOTE OF THE DAY
"In enterprise sales, value isn’t realized through features. It’s realized through outcomes."
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