2020 vs 2025: How Building Your First Sales Team Has Changed

If I had to build my first sales playbook today, I'd do it entirely differently than 5 years ago.

The 2020 Playbook (You'll Remember It)?

• Spray-and-pray email sequences.
• Zero clue about deliverability or domain setup.
• Pitching anything to anyone.
• Expensive CRMs managed by overpriced agencies.
• Lots of inbound leads.
• Mediocre salespeople hitting quota and earning big money.

That world is gone.

Gone for good. 🎶

What Changed?

Buyer behaviour. Fatigue. And AI.

Thanks to the old playbook, we now deal with buyers who:

• Overspent and have duplicate software with poor usage and expensive contracts.
• Need ROI to justify anything above €3-5K.
• Have a limited attention span.
• They are sick of "mediocre" reps.

And then came AI - automation, enrichment, data everywhere.

So, in 2025, building your first sales team requires three (plus one) things we forgot about:

Simplicity. Accountability. Execution.

1. Simplicity

You don't need a fancy agency to build your CRM.

Open Hubspot or Attio - 30 minutes and you're ready.

A basic pipeline, workflow, and a few reports are enough to run my solo business:

• Closed Won
• Pipeline Created
• Closed Lost
• ACV (month over month)
• Win Rate
• Time in Stage

That's it.

Don't overengineer it. What matters is consistency and clarity.

If I can live with that data, you can live too.

2. Accountability

The time for "I'll do it tomorrow" is over.

AI will soon think and act better than most reps - so there's no room for average anymore.

If you agreed to make 40 calls a day, do it.

If you're chasing a €30K monthly goal, you need €90K pipeline - three times coverage.

No excuses. Or as we say in Italy, "il resto sono chiacchiere."

Accountability means doing what you said you'd do - even when no one is watching.

3. Execution

Close to accountability, but more action-driven.

Curious about data enrichment or Clay? Learn it.

Want to automate your follow-ups? Try building your own AI agent this weekend.

Stop waiting for your company or your boss to show you how.

2025 doesn't reward "waiters." It rewards doers.

And, probably one of the most critical skills you need if you are in sales today is curiosity.

Not driven by scripts or BANT qualification questions, but by genuine curiosity.

3+1 Genuine Curiosity

Be curious with prospects.

Ask about their goals, processes, and pain points - not just to sell, but to learn. And if you can't help, just tell them. Move on.

Be curious about new tools. Experiment.

Be curious on LinkedIn.

Instead of endless scrolling cats, babies and selfies, follow 30–40 people who matter to your business.

Click the 🔔, study what they post, and engage with intent.

Curiosity compounds.

The Reality of 2025 (and beyond)

Next year will be harder.

Every year after, even more.

But we're also living in a time where you can build anything with almost no cost - a product, a service, even a new career (fractional ones included).

That's the paradox: tougher markets, but infinite opportunities for those who act with simplicity, accountability, execution, and curiosity.

2020 rewarded noise. 2025 rewards clarity.

So start simple. Be accountable. Execute relentlessly. Stay curious.

Because the founders and sellers who do these four things will still be standing when everyone else is blaming the market.

Thanks for reading this far - see you all next week.