In today’s newsletter, I’ll share why I think job security is an illusion in sales, and what you can do about it. I’ve been selling since I’m 15 years old (I prospected small aircraft owners to wash their airplanes), and I’ve sold everything, from professional services to influencer deals.

Instability and change have been constant in my journey, but it never prevented me from sleeping at night. There’s always an opportunity to make another dollar.

Here’s why I think job security is an illusion:

You’re only as good as your last quarter

If you’ve been in sales for a while, you know how it feels. When you reach your targets, you get all the spotlight, you’re part of the family, and everyone comes to you for advice and war stories.

But as soon as you miss the mark, you’re just a number. And if you keep missing the mark, you’re put on a Performance Improvement Plan, right before departing the company in the next round of layoffs.

That’s the reality of working in sales. The upsides are immense, but the downsides are deep.

Your manager will get replaced every 12 to 18 months

You’re not the only one to feel the pressure. Imagine being responsible for your own quota + the one of 3 to 5 other colleagues. If one of them misses the mark, you’ll have a few weeks to help, otherwise you need to fire them.

That’s what your manager has to deal with. If you thought your job was stressful, try managing a sales team.

As a result, your manager will last 12 to 18 months before being:

• fired
• put on a pip
• burn out and quit

I’m intentionally being dramatic, but changing managers is a constant in sales, which means you’re potentially 18 months away from working with psychopath (power-hungry people often share this trait).

Technology is making everything obsolete

In case you didn’t notice, we’re living in the world of tech and AI. New tools emerge every week and some of them wipe out entire business units in months. Look at the translation industry.

Luckily, sales isn’t too impacted by these changes (for now). AI SDRs are disappearing as quickly as they appeared, and salespeople are realizing that AI won’t replace them just yet.

But I can guarantee you that tech will keep disrupting entire industries, and destroy jobs that everyone thought were safe (it will create a lot of other jobs too).

What you can do about it

In my opinion, good salespeople know how to find a wave, surf it as long as they can, and find a new one when the old one is dying (I’ve never surfed, but I thought this analogy made sense).

When you accept this reality, you can start working on building a system to keep finding new waves, ride them, and repeat. Instead of working for a single employer, and praying for things to work, you can develop a portfolio career, where you find shorter-term contracts so you can test out the wave before fully committing.

This may seem scary to most people, but building a portfolio career is a process, not a radical decision you take.

If you’re interested in starting this journey, I have created a Portfolio Career Launch Plan. It’s a 15-seconds survey, where you answer a few questions about your current situation and your skills, and I send you a personalized plan, with contract ideas and suggestions. You’ll also be signed up to my Portfolio Career Waitlist, where I document my journey building a system to help you work when, where, and how you want.

Hope this helps.

Cheers,

Thibaut Souyris

In today’s newsletter, I’ll share 5 types of side gigs you can land, right now, without having to become a content creator, or post anything on LinkedIn. Working in sales means you have skills that are highly sought-after.

Most businesses owners look for these skills by opening a full-time, employed position, but you can also market them as a contractor (I prefer the term “Portfolio Professional”) for more freedom, money, and time.

Here are 5 examples:

Fractional Individual Contributor (SDR/AE)

A fractional Individual Contributor is an SDR or AE (or any IC position) that works on a part-time, fixed terms contract. Instead of joining a company as a full-time hire, without a set end date, you work as a contractor, with fixed terms.

For example, you could work 1 day a week as a fractional SDR, where you focus on booking meetings for your customer. You’re paid a fixed, hourly price, plus a set bonus for each meeting you book.

Fractional Team Lead

A fractional Team Lead side gig is a great option if you have a bit of management experience. You can run weekly 1:1s and share reports with your customer, coach salespeople, and work on prospecting or closing deals if necessary.

For early-stage startups, this kind of role is in high-demand. As you have experience prospecting, closing, and managing, you can do a bit of everything as an interim team lead.

Fractional Head

Fractional Head is a good option if you have some serious experience as a front-line manager. You’re able to market your management skills and the flexibility you offer for a high-price.

For example, I closed a €10.000 contract to be a fractional Head of Sales Development for 36 hours of work on my second year working for myself. €277 per hour isn’t too bad in my book.

Fractional VP

This is the sweet spot if you’re an experienced VP or C-level. Most business owners are winging it, and sales is particularly hard to crack when you don’t have a ton of experience selling yourself.

If you’ve been building sales processes, hiring salespeople, or held strategic positions in your career, becoming a Fractional VP is a great way to get paid big money to help business owners get more clarity in their sales organizations.

Consultant

Fractional positions are great, but they can quickly turn into full-time positions, if your customers are satisfied of your results. And that’s exactly what’s going to prevent you from working when, where, and how you want.

That’s why I recommend selling consulting contracts. Instead of getting involved in the day-to-day of your customers (and risk getting sucked in), you can work on a project-based basis, with clear outcomes and boundaries.

There are countless ways to structure fractional and portfolio professional contracts. You can sell a pre-determined amount of hours or days you’re going to work every week, set a performance-based compensation (commission and bonus), or sell a fixed project, where your customers pay for outcomes (not hours).

If you want to find out what type of contract you could land, right now, I have created a Portfolio Career Launch Plan. It’s a 15-seconds survey with questions about your current job and situation. At the end of the survey, I’ll send you a personalized plan to help you land your first side gig.

Hope this helps.

Cheers,

Thibaut Souyris

In today’s newsletter, I’ll share 3 simple steps you can follow to book meetings with people in your network. Keeping your network engaged is a great way to generate opportunities, especially when working in the middle of the summer (it’s mid-august as I write this newsletter).

When you go to your network to start conversations, you’ll get a lot more replies, land potential introductions, and you’ll find more opportunities as a result.

Here’s how, step-by-step:

Step 1: Build a list of prospect

Start by building a list of people you would like to be introduced to. For example, if you’re trying to build a portfolio career and work for yourself, you can create a list of potential businesses you’d like to work with, and the founders of these businesses.

When I was preparing to leave the last job I ever had, I made a list of 15 – 20 companies I would be interested in working with. I would look for 2, 3 people inside of the organization, and I ended up with a list of 40 prospects.

Step 2: Build a list of people you can intro you

Once you have completed your list of introductions, you can create a list of referrals for these introductions. Go on LinkedIn, and consult each prospect’s profile individually. You should be able to see if you have shared connections.

List who could introduce you to these people. For example, I landed my first two consulting contracts thanks to an intro from my friend Pierre-Yves. He introed me to the COO of a Foodtech company, as well as the CEO of a Fintech company.

In some cases, people who can intro you may not have direct access to a prospect from your list, but they may know about other interesting people. For instance, after speaking with another friend, he didn’t know anyone from my prospect list, but he introduced me to two founders from his VC fund’s portfolio.

Step 3: Build your introduction sequence

By now, you should have a list of friends and acquaintances to contact, as well as a list of potential introductions to ask them for. Your next step should be to create a structured sequence to help you stay organized when asking for introductions. This sequence typically includes:

• A set of steps (touchpoints) to send
• A channel and media for each step
• A cadence (number of days to wait between each touchpoint)
• A message for each touchpoint

Here’s an introduction sequence example:

In today’s newsletter, I’ll show you the exact steps I follow when launching a new offering. I’ve been working for myself for 6 years, and I launched many different services and products.

Right now, I’m working on creating a system to help remote salespeople go from being employed with a single source of income to highly sought-after portfolio professionals, so they can choose when, where, and how to work.

Here’s how, step-by-step:

Step 1: Build 3 to 5 assumptions

Before launching a new offering, you need to come up with a few assumptions about the specific challenges your prospects are trying to solve. You may already have a good idea of the solution to these problems, but it’s irrelevant at this stage.

Here are 5 assumptions I have about experienced remote salespeople trying to work for themselves:

1. Salespeople don’t know how to market their skills → they think they need a product to sell to make money
2. They don’t thing they have anything to offer → they don’t know how to package their skills
3. They have golden handcuffs → they have great work conditions, so it’s hard for them to leave them
4. They know this won’t last forever → they sense that the market is shifting, and employers want everyone back in the office
5. Those who want to work for themselves want to do it within a year → when they made the decision to work for themselves, they want to do it quickly

Step 2: Do a LinkedIn poll to validate each assumption

Now that your assumptions are clear, you can start working on validating them with data from your prospects. At the time of writing this newsletter (August 2024), LinkedIn Polls are working well to generate good impressions and engagement.

Here’s a recent poll I did, where I validated assumption 5: