Every day, confident outreach gets harder.
The noise increases.
Buyers get more jaded.
What worked six months ago feels stale today..
So here’s the question: Are you part of the problem or the solution?
The irony? Sellers and buyers want the same thing—a faster, more efficient way to solve mission-critical problems.
When you look at it that way, you’re not imposing.
If your product is solid, your company delivers real value, and you have strong case studies and testimonials—there is zero reason why your outreach shouldn’t succeed.
Yes, the game is changing. But the best sellers are adapting—and so can you.
We have an entire Flight School dedicated to the full process, but if you need three quick fixes that will have an immediate impact on your outreach—like starting today—here they are.
Let’s go.
1. Shorten Your Outreach—50 Words or Less
Most sales emails and LinkedIn DMs are too long. Buyers don’t have time for five-paragraph essays.
You get 50 words.
Three lines.
That’s it.
There are a lot of great messaging frameworks, but here’s one that works every time:
- Why Me? – Make it crystal clear why you’re reaching out to them, specifically. Get a solid buying trigger, not a general, overused observation.
- So What? – What’s the immediate impact for them? Why should they care?
- What’s next? – Make the ask simple and tied to them? Their pain, not your solution.
Example:
What’s up, [Name] ?
Agencies dealing with Argentina payments are facing rising costs and delays.
ACME (Y-combinator/Sam Altman-backed) was founded to handle global payroll/hr in 100+ countries effortlessly. Some of our customers you probably know: AngelList, Help Scout, Padsplit.
Are you pulling your hair out around this?
Rep. John Doe
ACME
Y-Combinator ’17
2. Buyers Don’t Buy When They Understand You—They Buy When They Feel Understood
70–80% of sales messages (based on what I get) are far too selfish.
They’re all about you—your company, your funding, your product.
It’s why so many people DON’T like cold outreach.
And here’s the real truth: Buyers don’t care about you. At least not yet they don’t.
They don’t buy when they understand you.
They buy when they feel understood.
How to Fix It (Fast):
- Get better buying triggers – Reach out based on something specific happening in their world.
- Use their lingo – Speak how they speak, not in sales jargon.
- Focus on one problem – Keep it tied to a mission-critical priority.
Example (Not Great):
Hey [Name], I’m with ACME (Y Combinator-backed), and we help companies optimize global payroll. Would love to connect and see if there’s a fit.
Example (Better):
Hey [Name], saw you’re scaling in Argentina.
With inflation at an all-time high, a lot of teams are facing payment delays and rising costs—frustrating their nearshore teams.
We just helped [Similar Company] fix this in a few weeks. Their team gets paid on time, without extra fees—and morale has never been better.
As we say around here – happy team, happy life.
Are you in this boat as well?
What to Do Now:
Look at your last 10 messages. Are they about you or the buyer? If it’s the first, rewrite them.
This shift alone will instantly make your outreach more confident.
3. Get Your Touches Up- Seriously.
Up to 50% of reps give up after the first touch. Unreal.
You’re backed by an amazing company.
You’ve got a fantastic message after steps 1 and 2.
Now, it’s time to build your confidence.
Take 50 prospects and hit them with 10x touches in the next 14 days.
Yes, really. That’s 500 touches.
- Emails
- Calls
- Voicemail
- Text, if that works for your audience
The best thing you can do—for yourself and your prospects—is to get to Yes / No / Not Now as fast as possible.
If every sales process worked this way, deals would close faster, and decision-making wouldn’t drag out for weeks.
Instead, we all live in outreach purgatory.
Reps say they want to get in front of buyers—but not badly enough.
So what happens? A weak, inconsistent drip, drip, drip—three touches over three weeks. Like a leaky faucet. Annoying, but not enough to fix.
Until finally, the prospect gets so tired of it they either unsubscribe or send a half-hearted “not interested.”
That’s not confident outreach.
Confident Outreach Isn’t Luck- It’s a Process
There’s a lot that goes into this—ideal client profiles, messaging development, and perfecting the timing of your outreach.
And no, this isn’t easy.
But it’s also not complicated.
Grab a team leader. Pull in another BD rep. Make these three things happen.
- Tighten your messaging—50 words or less, straight to the point.
- Make it about them—use better buying triggers and their language.
- Get your touches up—10x the effort, get to Yes / No / Not Now faster.
Do this well, and it will change your results overnight.
Or, keep doing what most reps do—waiting, hesitating, and hoping for replies that never come.
