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:

In today’s newsletter, I’m going to do something a bit different. If you’ve been a long time subscriber of Tactical Selling, you know I mostly share tactical prospecting tips to help you start more conversations, and book more meetings.

I’ve been working for myself for 6 years, and every time I meet someone who would like to do the same (quite common these days), they have tons of questions on how I did the transition to working for myself.

I’ve recently started having more conversations with experienced remote salespeople, and almost all of them have the same observations about working for themselves.

1) Almost everyone I talk to would like to work for themselves, but they don’t know how to get started

Around 60% of people I surveyed on my website would like to work for themselves. All my friends working in sales keep telling me how tired they are to be working for their bosses, and many are playing with the idea of working for themselves.

But almost all of them don’t know how to get started. They don’t think someone would pay for their skills, they don’t know how to land their first contract, structure an offer, or manage a side gig while working a full-time job.

2) They don’t think they have anything to offer

Salespeople I spoke to are convinced no one would pay them for a short-term contract. They think they need to build a business, become a creator, or do stuff they don’t want to do in order to get paid.

3) They have golden handcuffs

Let’s be honest. If you work as an experienced remote salesperson, your life is often pretty amazing. You can work from home, you have a great salary, you skip the dreaded daily commute.

But you’re dependent on one employer, and when things stop working (they always do, eventually), you risk losing these work conditions, and you may even end up in an office job to pay the bills.

4) They know this won’t last forever

Despite having great work conditions, almost everyone I surveyed shared that they feared these benefits wouldn’t last forever. With return to the office policies, and shift in power from employees to employers, remote salespeople feel the pressure on their lifestyle.

5) Those who want to work for themselves want to do it within a year

Around 82% of people who said they wanted to work for themselves want to do it within a year. They have a strong urge to become independent, and to diversify their income streams.

They often have good ideas, but they don’t have a structured approach to validating and marketing them.

That’s where I want to help…

It’s becoming clear that experienced remote salespeople want something more than just a job. They want a say in when, where, and how they work.

That’s why I am creating a system to help these people go from being remote employees with a single source of income to highly sought-after portfolio professionals.

If this sounds like you, I have created a waitlist to share my findings as I’m building this system in public.

When you join the waitlist I’ll show you how to market your experience, without having to launch a business (or create content), so you can build your work around your life, not the other way around.

Hope to see you in there.

Cheers,

Thibaut Souyris

PS: Don’t worry, I’ll keep sharing tactical prospecting tips. I’m just going to expand on other ways you can use this skill to become more independent.

In today’s issue, I’ll share what I’m working on to help experienced remote salespeople go from being employed to highly paid professionals, so they can choose when, where, and how to work.

If you’ve been thinking of quitting your sales job to work on something more meaningful, but never did it because you had bills to pay, this guide will give you a clear next step.

Let’s dive in:

In today’s issue, I’ll share 3 simple questions to ask if you want to close a deal. These questions are part of ProActive Selling, a sales methodology developed by Skip Miller.

If you’re struggling to qualify your opportunities, these will help you test the energy of your deals, disqualify tire-kickers, and understand where to invest your time.

But first, here’s a short story:

In today’s issue, I’ll share 5 sales tools I can’t live without. I’ve tried hundreds of tools in my sales career, and most of them weren’t really helpful.

Sales tools are often great to automate repetitive parts of our job, but they often include a ton of useless features (all the AI email writers, icebreakers, etc.) and they end up wasting everyone’s time.

There are over 5.529 sales tools, in 25 sub-categories, and here are 5 I can’t live without.

In today’s issue, I’ll share my 2024 guide to video prospecting. Video prospecting has been around for quite some time, and it was really hot during COVID.

In 2024, many salespeople seem to have forgotten how to use video to prospect, which is a great opportunity to use this media to catch the attention of your prospects, and start more conversations.

Here’s how, step-by-step:

Step 1: Use LinkedIn native video

The first step is to use LinkedIn native videos. Native videos are videos that are recorded using the LinkedIn mobile app. Here’s a quick video where I show you how it’s done:

In today’s newsletter, I will walk you through an important mindset shift for salespeople:

Moving from booking meetings with total strangers only (net new logos), to booking meetings with people you already know.

This shift will drastically improve your prospecting results, as you’ll start a lot more conversations, and book more meetings as a result.

It’s important because it will change your focus from something that requires advanced prospecting skills – convincing a total stranger to meet with you, to something you naturally do every day – starting conversations.

Let’s dive in:

The biggest mistake

Most salespeople who are prospecting have one goal: turning strangers into customers. This approach is understandable, because that’s what they are measured on.

However, when you are focusing on booking meetings with total strangers only, you make your job a lot harder than it has to be. Without reaching out to people they already know (active customers, previous customers, partners, and so on), salespeople end up having less conversations, and losing motivation.

Before you know it, you’re sending hundreds of emails each week, without getting any reply, and you start worrying about reaching your targets. You change your messaging too often, and your inner voice starts doubting your capacity to book a meeting.

A better approach: focus on people you know

Here’s how I recommend building pipeline with people you already know:

1. Create prospect tiers: What type of people can you reach out to? Existing customers, past customers, lost opportunities, partners, etc. ?
2. Get accurate data: Is the contact info still relevant? What kind of trigger can you use?
3. Build a sequence skeleton for each tier: What concrete steps will you follow to get them to answer?
4. Write your messages: What are you going to write in your touchpoints?
5. Set time blocks and execute: How can you protect your time to get in touch with these people on a daily basis?

Example: Booking meetings with past customers

For example, let’s say you have a good amount of past customers, but no active engagement with them.

Start by following the 5 steps from above:

Create prospect tiers: From all these past customers, you may have some who churned, some who worked with you for a few months, or standalone projects. List every prospect type and assign them to a different tier.

Get accurate data: Now that you have your list, you need to make sure your information is up-to-date. Is their email or phone number still accurate (check Kaspr if you need good quality data)? Did they change jobs? Did they get promoted? Find all the information you can to make your outreach message relevant.

Build a sequence skeleton for each tier: With people you already know, your chances of getting replies are way higher than with total strangers. But you can’t expect everyone to immediately reply and jump on a meeting with you. Using 3 touchpoints over email and LinkedIn is preferable because it helps you preserve your relationship, without being too pushy.

Here’s a sequence structure you can use:

In today’s issue, I’ll share 3 key lessons I learned from the last sales job I ever had. If you can take these lessons and apply them to what you sell, you’ll be in a better position to start more conversations, book more meetings, and close bigger deals.

But first, a bit of context. The last sales job I ever had was an Account Executive position for a tech company based in the US. They had been successful in raising money and deploying their solution in many mobile apps on the US market. I stayed for a total of 5 months, before quitting and going on my own.

Here’s what I learned:

Lesson 1: If you don’t understand the product, your prospects won’t get it either

When you work for a startup, you may not have a product-market fit yet. The early funding is supposed to help the company find it, and help you sell you first deals. It’s especially true if you’re opening a new market (like I was supposed to do).

In many cases, the founders are convinced that their product is revolutionary, but they can’t quite explain you why. That was the case for me. I remember going to California for a 2-week onboarding bootcamp. I attended many product sessions, deal reviews, and so on, but I couldn’t grasp why people would buy what we were selling.

When I came back to Europe, I started prospecting and meeting prospects, but I was not capable to explain them what outcomes they would get from using the product I was selling. The pitch deck was focused on the features (woofing, as Skip Miller would say), but my prospects couldn’t care less.

Takeways:

• Nobody cares about your product
• Raising lots of money ≠ guaranteed success
• What works in the US may not work in EMEA

Lesson 2: A founder is often a terrible salesperson

This last job gave me the opportunity to understand that selling isn’t a natural quality of many founders. They may be great at raising money, telling a compelling story to investors, or telling white lies, but they are often too focused on themselves to be good salespeople.

At my last sales job, I had the opportunity to go meet prospects in Paris, with one of the co-founders of the company. He destroyed every single opportunity I had been working on by reciting his fundraising deck. He was bragging about the “award-winning” technology we used, the size of our team, the crazy growth of the company, and so on.

There was just one problem. All these prospects were French, they didn’t really understand English, and they didn’t have any space to share what they were working on.

Takeaways:

• Founders are often great at many things, but not selling
• Their obsession with scale will hurt your deals
• French people do not speak good English 😂

Lesson 3: It’s never about what you sell

This last lesson is the most important I learned from my last sales job. I had the opportunity to meet with Skip Miller during a 2-day training organized by the company, and it changed the trajectory of my career. I learned that everything your prospects are interested in is themselves.

They are only interested in understanding if your product can help them reach their targets, what outcomes it’s going to create for them, and how you can help them make a dent in their problems.

Takeaways:

• If you don’t know your prospects problems, you don’t have deal
• Nobody cares about what you sell, they care about outcomes
• If you had the chance to meet Skip Miller, you were blessed

And these are the 3 most important lessons I learned from the last sales job I ever had. I’ve been working on my own since September 2018, and I like to say I’m totally unemployable as a result. Leaving this last job seemed risky at the time, but it was the best decision of my life, as I found out I was able to make money on my own terms, without having to report to anyone.

Hope this inspires you to be more intentional with what you want to do with your life.

Cheers,

Thibaut Souyris