The First 90 Days

Hey friends,

I spoke to a founder last month who was literally panicking.

He hired his first AE two months ago. No closed deals yet. No pipeline.

He asked me, “Should I fire him?”. I asked: “What did you expect him to do by month two?”

Silence.

He had no answer.

Early-stage founders hire a sales rep, throw them in, and then two months later, they panic because the results are not there yet.

But if you do not know what “good” looks like at month 1, 2, and 3, you will either fire too early or wait too long.

Both are expensive.

Both are huge mistakes.

Let's put some order.

Month 1:

Learn, Role Play, Start Calling

The first month is about foundations.

Product, sales process, CRM, tools, culture. How you sell, who you sell to, and why customers buy.

But learning does not mean sitting in a corner reading docs for 30 days.

By the end of month 1, your rep should already be on the phone.

SDRs should be up and running with the script, the outbound process, and doing their first real calls.

AEs should know the product and the process, and they should also be doing some cold calling and outbound alongside shadowing demos.

What good looks like:

✅ Product knowledge is strong.

✅ CRM is being used properly.

✅ First calls are happening.

✅ Role plays are done internally, and you (the founder) are confident for them to be on the phone.

Red flag:

🚩They are still “getting ready.”

🚩They have not picked up the phone.

🚩They are waiting for leads instead of going after themselves

Month 2:

Selling and First Pipeline

Month 2 is where the real work starts.

Your rep should be fully active.

On the phone every day. Running outbound. Booking meetings.

For SDRs, you should see consistent activities and the first qualified meetings booked.

For AEs in SMB or mid-market, the first pipeline should be showing up.

Real deals in the CRM with next steps, close dates, and amounts.

For enterprise AEs, the pipeline may take longer. But the activities and conversations should be there.

What good looks like:

✅ Activity targets are hit

✅ The pipeline is being created

✅ The rep applies feedback.

Red flag:

🚩Low activities.

🚩Excuses.

🚩Complaining about the leads, the product, the market.

And the biggest one: lack of coachability. If you give feedback and nothing changes, that is your signal.

Month 3:

Fully Ramped - It's time To Close!

By month 3, your rep should be fully ramped on pipeline.

For SMB and mid-market, the pipeline should be growing from month 2. The first closed deal should come in around this time. Ideally, self-sourced through outbound.

For the enterprise, the first real pipeline should now be in the CRM. Closing takes longer, but the foundation should be there.

What good looks like:

✅Pipeline is real and growing

✅ First deal closed or close to closing

✅The rep operates independently.

Red flag:

🚩Still no pipeline.

🚩Still blaming external factors.

🚩Still not applying what you coached.

The Pattern That (may) Predict The Future

In my experience, reps who do not make it show the same three signals early:

1. Complaining. About the product, the leads, the territory. Always something external.
2. Low activities. They are not on the phone enough. The numbers are simply not there.
3. Lack of coachability. You tell them something, they nod, and nothing changes.

If you see all three by month 3, you have your answer.

Do not wait until month 6.

Nothing is going to change.

In the same way, the patterns that predict success:

1. Pipeline growing
2. Activities up
3. Feeling and sounding good in calls.

These are the signals you got yourself a strong rep. Congrats!

Either way the first 3 months are crucial, get yourself prepared.

Thanks for reading. See you next week!

– Matteo