In today’s issue, I’ll share what I see as the true price of working remotely. I’m writing this newsletter from a co-working space in Berlin (I live in Mexico normally), and I could be writing it from anywhere, thanks to my remote work setup.

This is one of the many benefits of working remotely. You get to choose how you organize your time, where you work from, and you have more control over your workday.

But all this freedom comes at a price. And you need to know about it if you want to keep living the dream life.

Let’s dive in:

Why working remotely is so interesting

Working remotely sounds like the perfect setup. You avoid rush hours, you save on gas, restaurants, and you can organize your work as you wish. Some companies even reimburse remote office setups. It’s a fantastic work situation if you’re already experienced, and you want to organize your work around life, not the way around.

It’s also liberating to avoid forced social interactions with your colleagues. If you’re an introvert, it drains less of your energy, and it’s a great way to stay focused on the task at hand. There are mostly benefits to working remotely if it’s something you choose (vs being forced to work remotely when you need an office environment to stay focused).

But working remotely comes with a set of problems that you can’t ignore:

Problem 1: You’re giving up job security

Working remotely means working from home for most people. You’re not allowed to work from abroad (or for a very limited time), and your employer is constantly tracking when you log in, and trying to control your work environment.

Real remote work implies working from where you want, when you want. In a lot of cases, this type of setup means you have to give up your employee status (and all the benefits that come with it) to become a contractor. Concretely, you’re giving up job security and you’re employer becomes a customer.

To me, this is the definition of freedom, but it’s a stressful situation to be in for most people.

Problem 2: You’re on your own

Working remotely means being physically alone. No water cooler discussion, no office gossip, no lunch with your colleagues. If you ask me, that’s paradise. But it’s hell for a lot of people. Humans need social interactions, and Slack messages or Zoom meetings don’t replace the physical need we have to be around other people.

Career progression also suffers when working remotely. Being in an office with your colleagues helps create political soft power. You get to spend time with people who can impact your career, and a lot of this soft power is built unconsciously, through daily interactions with your colleagues.

Problem 3: You can never really go back to working in office

The last big problem I see with working remotely is that you can’t really go back into working in an office every day if you’ve been used to a remote role. I’ve met a lot of salespeople who worked fully remotely for years, before being laid-off and having to accept roles that were a 100% in office.

All of them are miserable. They had built a life in their own terms, but were forced back into a way of working that completely clashed with their view of life.

All of them are in existential crisis.

They need the job because they have to pay the bills, but they hate their lives. A lot of my friends live in Germany, and they work for a year, reload their unemployment benefits, and stop working for a year, before starting the cycle again.

And they are DEPRESSED.

That’s why I came up with an idea. I’m planning a retreat in Mexico for remote salespeople who are in an existential crisis. If that’s you, please join the waitlist and reply to the follow-up email, I want to talk to you.

And this is the true price of working remotely. You get to live the dream life, but it can get taken away at any time, and you have no control over it. One day you’re making 6-figures working from wherever you want, the day after you get laid off, with two weeks severance.

There has to be a better way.

Hope this helps.

Cheers,

Thibaut Souyris

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 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

In today’s issue, I’ll share my top 5 sales tools for remote sales. There are over 5.529 sales tools in 25 sub-categories available to help us sell more. Finding the right tool for your need has become incredibly time-consuming. Most tools now claim to revolutionize how we sell with AI (spoiler alert: they don’t).

That’s why I’m going to share 5 tool categories (and examples) that you can’t afford to ignore if you’re selling remotely.

Let’s dive in:

Category 1: Sales Engagement tools

A sales engagement tool helps you structure your prospecting efforts. They can range from a simple sequencer to a full suite of prospecting tools, including lead research, sequencing, auto-reply, AI-assisted lead engagement, etc.

Here are 3 tools I recommend (I’ve tried all of them):

• Amplemarket: If you’re looking for an all-in one sales engagement tool, then Amplemarket is the one for you. That’s the tool I use every day to manage my prospecting, and it has absolutely everything you need. Ideal if you’re a sales leader with a big team.
• Reply.io: If you’re looking for a simple sales engagement tool, Reply.io does a lot of what Amplemarket does, but with a simpler setup and a lower price. Ideal if you’re prospecting by yourself.
• The Prospecting Tracker: The Prospecting Tracker is a simple Notion tracker I have created for salespeople who cannot choose their engagement tool (when their employer don’t want to switch tools). Ideal to get started.

Category 2: A CRM

A CRM is the most important sales tool to help you keep track of your deals. Most remote companies use Salesforce or Hubspot, but here are two simpler CRMs I recommend:

• Pipedrive: If you need a simple system to keep track of your deals, with a simple learning curve.
• Monday.com: Fully customizable CRM. A bit harder to set up, but ideal if you’re managing a team and want fully control on your data.

Category 3: A calendar link

A calendar link is a tool that allows prospects to book some time with you, without having to go back and forth. Here are 3 that I recommend:

• Calendly: I personally use Calendly since 5 years. Really simple, straight to the point, and you can even integrate with Stripe to get paid.
• Chili piper: The best platform to convert demand into pipeline. More complicated to set up, but a must for sales teams with more than 1 person.
• Built in links in Google: A recent feature Google has added to its calendar. Ideal when you’re getting started.

Category 4: A data backup

When using email and phone to prospect, you’ll find a maximum of 70% of the email addresses and phone numbers if you use one provider only. That’s why I recommend using at least one additional data provider to help you find the right data (especially if you’re selling outside of the US).

• Kaspr: The best tool to find mobile phone numbers. I’ve been working with them for a while and they never disappoint.
• Dropcontact: A great tool to find accurate emails, especially if you’re selling in EMEA.

Category 5: An e-Signature tool

Finally, an e-signature tool is a must if you’re selling remotely. Instead of sending contracts, getting prospects to print them, scan them, and send them back, you can use one of these tools to get the contract signed. They often have features for automatic follow-up with prospects.

• Pandadoc: The ideal tool to get contracts signed today. Really simple to set up.
• Docusign: The Enterprise solution you need if you’re selling to traditional verticals.

And these are the tools I recommend when selling remotely. You won’t need much more than that to do what matters in sales; prospecting, managing your deals, speaking to customers, and signing contracts.

Hope this helps.

Cheers,

Thibaut Souyris

In today’s issue, I’ll share how I manage my time as a remote sales guy. When selling remotely, it can get really hard to create a clear physical and mental boundary between your professional and your personal life. You end up working when you should be with your family, or doing chores when you should be working.

I’ll tell you about what you should focus on, how to set boundaries when working remotely, and what tools you can use to protect your time.

Why managing your time is so hard when selling remotely

Back in 2020, I got forced (like everyone else) to work from home. I wasn’t expecting to have difficulties managing my time, but after a few weeks running in circle, I started getting anxious.

At first I didn’t realize it, but the creeping anxiety came from not having a strict routine and no boundary between my work and my personal life. I was sleeping, working, eating, doing sports in the same place, and it drove me crazy.

That’s when I decided to build a routine to build a mental boundary between the important aspects of my life.

Here’s how, step-by-step:

Step 1: Focus on critical activities first

When working in sales, you have different types of tasks and activities. Some are proactive (like prospecting), some are reactive (like taking an impromptu call with a prospect). I recommend listing all the activities that you typically do in one day, and rank them by priority.

Here are my typically sales activities during the day, ranked from most critical to least critical:

• Prospecting
• Running discovery calls
• Following up with active opportunities

First thing I do in the morning is prospecting. I spend 30 to 60 minutes following up with prospects, finding new prospects, and contacting them. Then I have a slot where I group all the discovery calls of my day (typically after the prospecting block). When it’s done, I focus on moving deals further (and disqualifying).

Step 2: Set clear boundaries

When I know what my critical activities are, I create a daily ritual to make sure I’m not getting distracted by other reactive tasks.

For example, I’ll block 60 minutes from 8AM to 9AM for prospecting. I also have a “Sacred Hour” block every day from 11AM to 1PM so I can focus on deep work tasks (the ones where I need to be ultra-focused). Here’s what my calendar looks like:

In today’s issue, I’ll share 3 simple steps to build a solid prospecting routine, using Claude (or ChatGPT). Many salespeople are trying to scale their outreach with the AI tools that are available to them. As a result, prospects get SPAMMED with tons of soulless cold emails, LinkedIn messages, or even LinkedIn comments. It’s tiring for everyone, and we end up asking ourselves if this AI thing is not just a bubble.

Here’s are 3 concrete steps you can follow to build your prospecting routine with Claude:

Step 1: Explain your problem to Claude

When working with an AI, your first step is to explain what you want from this AI. A good way to explain your 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 build a prospecting routine if I was an AE who got asked to start doing outbound:

Hi there, it’s Thibaut.

Welcome to the Remote Sales Playbook.

In this newsletter, I primarily cover:

• How to create solid prospecting systems and routines (that get your 30%+ reply rates)
• Concrete tactics to qualify deals, close them faster, while wasting less time with unqualified prospects
• Tips, tactics, and strategies to help you work when, where, and how you want (as a remote salesperson)

But I’ve been writing this newsletter for a while now, over 3 years!

And I want to make it as easy as possible for you to find issues that are most relevant to you.

So, here are some of my favorite issues… organized by topic.

How to create solid prospecting systems and routines (that get your 30%+ reply rates)

The topic I probably write about this most is prospecting.

So, if you’re looking to finally get prospects to pay attention to your messages and/or reach your prospecting targets I’d start here:

• How many prospects you should contact every day: A simple formula to find out how many prospects to contact daily if you want to reach your targets.
• How I booked 12 meetings with this simple LinkedIn connection request: A killer connection request template for LinkedIn.
• 5 steps to building your prospecting routine: A playbook to make sure you prospect the right way.

Concrete tactics to qualify deals, close them faster, while wasting less time with unqualified prospects

Another topic I write about frequently is closing. How to turn a stranger into a customer.

So, if you’re looking to stop wasting time on tire kickers and/or reach your sales targets, I’d start here:

• 3 simple questions to ask to close a deal: A qualification framework I love using to know if I’m talking to people who are serious about a deal.
• 3 steps to close a deal today: A tactic I use all the time to get people to commit to a deal and sign it on the same day.
• 3 steps to fix your pipeline: A methodology I use to clean up my pipeline and make sure I’m investing my efforts with the right prospects.

Tips, tactics, and strategies to help you work when, where, and how you want (as a remote salesperson)

Finally, a personal favorite topic of mine is independence. I love sharing tips to help salespeople diversify their income streams, and get more freedom.

So, if you’re looking to start building a life in your own terms and/or diversify your income, I’d start here:

• If you’re a remote salesperson, you need to read this: A must-read if you’re working remotely and got used to setting your own rules.
• 5 side gigs you can land right now: 5 concrete ideas to start working for yourself on the side.
• How to avoid burning out as a remote salesperson: A simple resource to help you organize your time (and set boundaries) when working remotely.

In today’s newsletter, I’ll share my updated LinkedIn Connection Request Guide. LinkedIn connection requests are incredibly powerful for salespeople when used the right way. But most are using them to pitch slap their prospects, and they miss an opportunity to start real conversations.

Here’s how you can solve that, step-by-step:

Step 1: Optimize your LinkedIn profile

Before sending a connection request, you need to make sure your LinkedIn profile is optimized for prospecting. A lot of profiles look like trophy shelves, or provide zero information on how they can help prospects solve important problems.

Here’s what you need:

• A professional profile picture (use Secta to create one with AI)
• A clear headline (what you do, who you help, what’s the outcome of working with you)
• A catchy LinkedIn banner (this guy did mine)
• An optimized featured section (a free resource to help prospects + link to your calendar link)

Don’t miss this detailed guide to optimizing your LinkedIn profile.

Step 2: Understand the connection request process

Most people use LinkedIn on their mobile phones. There’s just one problem; 99% of salespeople prospect with their computers. Here’s what your connection requests look like on both formats: