In today’s issue, I’ll share why I think AI can (almost) entirely replace working in an office environment for remote salespeople.

I remember when I started my tech sales career, I was 24 and I had just moved to Berlin. It was back in 2015, and we were working 100% in an office. At the time, I loved it because I barely knew anything about sales, and being around my colleagues was the best way for me to learn. From running discovery calls, to listening to my colleagues close Enterprise deals, I was able to enjoy the Collective Brain of the office.

Now, imagine working remotely. You’re by yourself in your home office, Slack notifications going off every 10 seconds, and when you join your team meetings on Zoom, almost all cameras are off, and all of your colleagues are muted. You have no chance to learn from the Collective Brain of the office.

Let me show you how to solve that with AI:

The big problem with remote sales

Here’s a story for you.

My big brother used to work in the hospitality sector for 10 years before becoming an SDR for a remote tech company. He’s one of the hardest working person I know. He’s organized, he knows how to structure his day, and he is self-motivated. But he stayed in tech sales for 9 months only.

The main reason?

He felt lonely. He wasn’t able to feed of the energy of his colleagues, and he failed because he didn’t have access to the Collective Brain.

And that’s the main problem with working remotely. You don’t have any real human interaction, and it’s hard to learn anything from your colleagues when their cameras are off and their mics are on mute.

But you can solve a part of this problem with AI, here’s how:

Step 1: Explain your problem

I refer to the Collective Brain as the spontaneous knowledge that is created when groups of people work together in the same physical environment. Think about the last time you were at a team meeting, a party with friends, or simply with your family. There’s something special, some kind of energy and knowledge that is created, spontaneously.

You can use AI (ChatGPT or Claude) to emulate that knowledge, and solve problems. A good way to explain a problem is to follow this 4-step framework:

• Context: Give context about your situation, and what’s your problem
• Role: Give the AI a specific role
• Task: Give a task to the AI
• Format: Format the way the AI will ask you questions

Here’s an example I used, to help me close and important Enterprise deal at the end of the quarter:

In today’s issue, I’ll share my ultimate guide to closing your Q1 strong. I’m writing this newsletter on the 19th of March 2025. There are 9 business days remaining in Q1. If you’re like most remote salespeople I know, you’re far away from reaching your Q1 targets, and you’re getting desperate to close the deals in your pipeline before Monday 31st of March.

The good news is that you need to ask 3 simple questions to find out if your deal will close in Q1. The bad news is that you’re most likely not going to close these deals if you don’t have an answer to these questions already.

Let’s dive in:

The problem with most deals in your pipeline

If most of the deals you were working on in Q1 are still open, you’re in bad position. The chances of them closing next week are slim.

Why am I saying that?

Because most salespeople are afraid of disqualifying deals that have no chance to close this quarter. I’ve done it many times myself, and it’s always been a big contributor to missing my sales targets. Instead of asking tough questions that will most likely put the deal status on “Closed Lost”, salespeople prefer waiting and hoping for their prospects to magically send them a signed contract.

Here are 3 simple questions to find out if your deals have a chance to close.

Step 1: Ask what’s causing them to have conversations with you

This is one of the first questions you need to ask in your next conversation with your prospect. Instead of asking them why they are here, ask them “What’s causing you to have a conversation with me?”

This will help prospects open up and share the real reasons they are in the meeting with you. Some may just be curious (don’t waste your time with them), some may have a specific initiative and deadline they are working on (dig deeper).

Step 2: Ask what outcomes they want from your conversations

Second question will help you understand your prospect’s initiatives. By focusing on asking what outcomes they expect, you get them to share the agenda and goals they have for the conversation.

This will help you dig deeper, and disqualify prospects who may not have a compelling event. For example, if they answer that they are just checking or making a benchmark, you’ll know you can disqualify them and end the conversation as soon as possible.

Step 3: Ask when they can make a decision

Final question, and my favorite of all three. By asking prospects when they can make a decision, you do two things:

• you test the energy of your deal
• you understand their buying process

Most prospects won’t be able to give you a straight answer. This indicates they’ll have to involve other people in the buying process, and you can ask them additional questions about the steps required to close the deal. If that’s the case, you need to lay down a clear plan to get a conversation with their boss before the end of Q1, otherwise you won’t close the deal.

And these are 3 simple questions I recommend asking to understand if your deals have a chance to close in Q1. I’d love to give you a secret play, but there isn’t. If your deals aren’t qualified, and you’ve been working on them for a long time, prospects won’t turn into customers on your timeline, but on theirs.

Hope this helps.

Cheers,

Thibaut Souyris

In today’s issue, I’ll share why I think using AI for prospecting is a terrible idea. I’ve been posting on LinkedIn every weekday since 2019, and what was a great space to share tactical sales tips became crowded with memes, Gen-Zs sharing their make up tips, and “entertaining” sales content.

I can’t click the “Unfollow” button fast enough.

And there’s one main reason for this mess (we see it in all other platforms too): Artificial Intelligence. We can see its effects in cold outreach too. Tons of messages are sent by AI agents daily, crowding prospects’ mailboxes and LinkedIn DMs.

Here’s why it’s so bad, and what you can about it:

AI is terrible at finding good leads

I’ve tested tens of sales engagement tools promising to use AI to help you find perfect, hot leads. If you follow the instructions provided in the onboarding, you get a list of totally random people. The results are exactly the same as other lead generation tools that don’t use AI.

The main problem with the promise of AI finding leads for you is that most of these tools do not provide you with the right use case for AI. Almost all of them give you an empty text box, where you need to describe your Ideal Customer Profile.

I’ve been training thousands of sales reps, and 99% of them have no clue how to describe their ICP. So when writing a prompt, they write generic descriptions, like “I sell to sales leaders in tech companies”. Not surprising that they end up with a super generic list of prospects.

AI is terrible at writing messages

The worst AI use case I see in sales is around copywriting. Here’s what an AI-generated cold email looks like:

In today’s issue, I’ll share the exacts steps I follow to build a remote prospecting system. When selling remotely, it can get challenging to prospect. You don’t have a boss on your back, checking your activity, and you can easily procrastinate. Without the energy of a sales floor, creating consistent prospecting results is a lot harder than it looks.

I’ll show you how you can address this challenge in 3 simple steps.

Why remote prospecting is different from office prospecting?

Remote prospecting is quite different than prospecting from an office. When I started in tech sales in 2015, I joined a team of 30 in Berlin. We were all prospecting from the office. There was a great vibe, and a healthy competition. We were all opening new markets, and the camaraderie helped us book a ton of meetings.

Now imagine prospecting from your home office. You’re sitting alone in your bedroom, only interrupted by the noise of Slack notifications. If you want to speak to someone, you need to send and invitation, jump on a Zoom meeting, and fight with your camera to work. If you start getting tired, you can easily go for a quick nap, or start doing your chores.

This environment is the absolute worst if you want to prospect, which is why you need to create systems and rituals to fix your environment.

Here’s how:

Step 1: Plan your prospecting system

Let’s be honest, prospecting isn’t fun. You keep repeating the same task over and over, you get rejected a lot more than you’d like, and your only reward is a meeting booked (which has less than 30% of turning into business). It’s super hard to do consistently.

If you want to prospect regularly, you need to start by protecting your time. When it’s done, I recommend starting with follow-up messages, then finding new contacts to add to your sequence (determine how many you need here). When you’re done, add these people to your sequence (send them the first touchpoint), and you’re done for the day!

A prospecting system also needs a solid sequence. It’s a set of steps you follow until you either get a reply, or run out of steps. Here’s how I recommend creating your sequence.

When your sequence skeleton is done, you need to define what you’re going to write or say. I recommend using my prospecting template swipe file to do so.

Step 2: Get some quick wins

There’s a crazy misconception about outbound prospecting.

Salespeople believe their meetings won’t be worth as much if they are booked with someone they know, over a total stranger. I believed that for years, and my trajectory completely changed when I started including people I knew. Instead of chasing net new logos, contact past or current customers, lost opportunities, or people you know outside of work (they have to be relevant though).

This doesn’t mean you shouldn’t contact people if you don’t know them, but it will make your prospecting more interesting because you’ll get a few replies and you won’t just get people ignoring you.

Another thing salespeople focus too much on is planning. They get stuck in the ideation phase, tweaking their messaging and channel before getting started. Instead, define your activity target (use the sales process calculator), create a quick sequence, and send messages.

At first, you won’t get much results. Your first two weeks will be the toughest. But if you prospect every single weekday, you’ll reach an optimal activity level, and you’ll gather enough data to understand what works and what doesn’t.

Step 3: Track early signs of success

I remember when I started my first sales job. I was obsessed with closing my first deal. You could feel it in everything I was doing. My prospecting messages where focused on getting people to sign, and all my calls were extremely pushy and aggressive. Josh Braun calls this the “commission breath”. That’s the biggest mistake I see when coaching salespeople.

Instead of obsessing over closing deals, focus on your early signs of success.

When using email, your first sign of success is your email landing in the primary inbox of your prospect (sounds obvious, but a lot harder than you think). If you’re having trouble with this, I recommend checking Maildoso. Your second sign of success with email is the open rate. Anything under 50% has to be worked on.

When using LinkedIn, your early sign of success is the invitation acceptance rate. If people do not accept your invitation, you won’t be able to message them, send them voice notes, or videos.

This is how you can build a simple remote prospecting system. Plan your system, get some quick wins, and track your early signs of success. And if you’ve already tried all this, but you need more advanced support, then I recommend checking my Prospecting Engine.

Hope this helps.

Cheers,

Thibaut Souyris