Will Aitken

Trust Me, I'm a Salesperson | Sales Trainer, Keynote Speaker, Author, and Pisstaker | Fluent in English, Memes, & Sarcasm 🇬🇧🇨🇦

Just another LinkedIn sales influencer... but funnier and better looking than most.

Born in 1994 in the roundabout filled town of Milton Keynes I was always the odd child at school. 

After getting the worlds most pointless degree at University of Brighton I decided to go “find myself” by working in a French Ski Resort, backpacking through south-east Asia, before temporarily settling down in Sydney Australia where I got work as a recruiter and then moving to Canada. 

Now in North America I was determined to work in SaaS sales because I saw on Reddit that you can make BANK selling software.

Just a couple of years later after trying to find my footing I was the top rep on my team.

This gave me time to open up TikTok and on April of 2021 I made my first video, then I made one everyday for 6-months. 

This opened up my love for content creation and led me to my current career in marketing, keynotes, book writing, and sales training. 

Expertise include: New Business Development, Account Management, Cold Calling, Sales Proposals/Presentations, Marketing Product Knowledge (SEO, EDM, Retargeting), Recruitment Services, Headhunting, Email Prospecting, Vice President (SEO purposes), VP, CEO, LinkedIn Recruiter/Sales Navigator, Boolean Blackbelt, Training, Sales Kick Offs, Speaker, Speech, Sales Management, and Fixing Up to Look Sharp.

Chief Vice Directing President of Managing Things

I provide training, coaching, courses, keynotes, and merch for sellers and sales teams! Check out my offerings on willaitken.com

Made some cold calls during a training with a biotech company in SF last week

The CEO “How did you just do that? You don’t know anything about our product…”

He was right, I don’t know the first thing about protein stability, viscosity, and aggregation data 😂

But that’s also the point… 

A call should have nothing to do with the product and everything to do with the prospect

You don’t need to be a biologics expert to ask someone questions

Just another LinkedIn sales influencer... but funnier and better looking than most.

Born in 1994 in the roundabout filled town of Milton Keynes I was always the odd child at school. 

After getting the worlds most pointless degree at University of Brighton I decided to go “find myself” by working in a French Ski Resort, backpacking through south-east Asia, before temporarily settling down in Sydney Australia. 

It was in Sydney I met my Canadian wife and found a passion for earning lots of money as a recruiter. 

Like a high quality European Lager she imported me back to her hometown in Charlottetown PEI.

Now in North America I was determined to work in SaaS sales because I saw on Reddit that you can make BANK selling software.

Just a couple of years later after trying to find my footing I was the top rep on my team.

This gave me time to open up TikTok and on April of 2021 I made my first video, then I made one everyday for 6-months. 

This opened up my love for content creation and led me to my current career in marketing, keynotes, book writing, and sales training. 

Expertise include: New Business Development, Account Management, Cold Calling, Sales Proposals/Presentations, Marketing Product Knowledge (SEO, EDM, Retargeting), Recruitment Services, Headhunting, Email Prospecting, Vice President (SEO purposes), VP, CEO, LinkedIn Recruiter/Sales Navigator, Boolean Blackbelt, Training, Sales Kick Offs, Speaker, Speech, Sales Management, and Fixing Up to Look Sharp.

Follow-up is far from dead

But the way I see most sales teams run sequences/cadences is 👎 

Same 2020 playbook:

- 1 or 2 universal cadences
- Dump thousands of contacts in
- Generic personalization fields
- Pray that step 37 does the trick

That’s the exact noise that's made it so easy for buyers to tune us out

What actually works now isn’t sexy, it's being more thoughtful with:

- More prep
- Smaller lists
- Messaging built around real signals

Instead of one "do-everything" cadence, it's running multiple (potentially dozens) of much smaller + specific ones

Examples 👇

Sequence 1
Persona: VP of Sales
Company: 10-50 reps
Signal: Recent SDR headcount reduction

Sequence 2
Persona: CRO
Signal: Downloaded marketing content

Sequence 3
Persona: Frontline Leader
Company: 50+ employee Construction Tech
Signal: Similar space to an existing successful customer

Each one gets:

- Different problem framing
- Different social proof
- Different offer
- Different CTA

I write most of my emails manually now, but this could be automated without losing relevance if the inputs are right (quality data, segmentation, highly relevant signals)

Talking all things cadences today at 12pm ET with Aaron Reeves on the Daily Sales Show

He’s breaking down how reps are getting 15% response rates from fully automated cadences by doing the opposite of what this meme shows

Jump in and learn - https://hubs.la/Q03YV5F-0

EDIT: One of my favourite shows in a long while, absolutely packed with value, recording is available via that link! (Plz excuse the two Brits talking at a million miles an hour)

What if we used LinkedIn connection notes as pickup lines? Ft. Amanda Nielsen 🐶

Want to up the creep factor? Try adding:

"I've been following you for a while 👀"

I grow partnerships @ Box 📦 I turn tech memes into merch @ Thot Leader Labs 🦄 I coach people pivoting into partnerships 🌱

Omesh  Moorjani

They were a really good fit prospect tbf 🤷‍♂️ 


Got a new SDR or want to level up your cold email game in 2026? 

Jump on this cold email masterclass with Florin Tatulea and Brian LaManna at 12pm ET - https://hubs.la/Q03YV1rx0

Stupid simple switch for cold call openers:

"Hey Steph it's {name} from {company}, giving you a call because {reason}, got a moment?"

"Hey Steph giving you a call because {reason}, it's {name} from {company}, got a moment?"

Most of the time, leading with your name and company will put someone in "do I know this person" mode (it's a cold call so they probably don't)

It'd be weird not to include it, but better to lead with your reason/research

This ain’t a Q1 pipeline, it’s a graveyard 🪦

One of the most underrated traits in sales isn’t confidence.


It’s the opposite, being humble enough to say “I might not know everything, and I want to learn”

That applies both when you’re speaking to clients and when you’re trying to get better at the craft

On Friday we ran a GAP Prospecting training for the Unchained Labs sales team at the tail end of a long in-person company kick-off event

Everyone was tired from a week of travel to the HQ, socializing, learning, and hearing company updates

It would’ve been very easy to sit back, coast, and daydream about plans for the weekend

That didn’t happen, the team leaned in:

- They challenged me
- They asked for help & feedback
- They pressure-tested ideas instead of defending old habits.

Nathaniel Reynolds even volunteered to make a cold call in front of everyone in the room

That’s the difference between top sellers and those who crash out

People who say “I’ve got it all figured out” might win short term

But people who say “I’m always open to learning” build careers that compound

Recording the GAP Prospecting audiobook with Keenan in Denver this week! 🔥

Now I’m pretty good at improv & public speaking

But my kryptonite? Dyslexic as heck

So reading books/scripts aloud has always been a challenge

I’m especially haunted by the memory of my first English class at new high school

We were reading “Of Mice and Men”

Each student had to stand up and read a page out loud

As each student finished their page with ease, I got more and more anxious, and soon it was my turn

I stood up shaky and read my page

I stuttered over Lenny’s dreams of owning rabbits, stumbled over George’s reassuring plans if owning a farm, and had to restart sentences about Curley’s vaseline filled glove as my mouth tried to move quicker than my eyes and brain 

I vividly remember a girl I had a crush on turn to her friend giggling and whisper (loud enough for me to hear) 

“Oh my gosh, he can’t read”

That memory still stings 18 years later 🥲

So is there a sales takeaway here or am I just trauma dumping? 

Well much like Mice of Men, if I read directly from a script/list of questions that I didn’t write then I’m not going to sound natural 

But if I know the material well then I can trust myself to say the right thing in the best way

That’s true in the studio this week

And it’s true every time I pick up the phone to make a cold call or hop on a discovery meeting with a prospect

When I’ve practiced out loud, tripped over the words in private, rewritten things in my own language, and slow my pace…

I can show up confident and present when it matters most

That’s why I encourage EVERY SELLER partake in the uncomfortable practice of roleplaying alone, as a team, and now with AI voice tools

To internalize the important stuff so we’re not using brain calories thinking about what we need to say in the moment

Read, make it your own, memorize, and it’ll be a million times better than reading the “perfect script”

TLDR: Reading isn’t the skill that matters, preparation is

(and GAP Prospecting will be out on audiobook from day 1, so if you’re not on the waitlist yet yell in the comments and I’ll hook you up)

Which of these examples do you emotionally connect with more, the gain or the pain?

Keenan and I go hard on problem-centric selling in GAP Prospecting 

Most of the time buyers *relate* far more to what could be wrong with their current state vs. *imagining* what could be better with their future state

In other words, people psychologically connect more with:

Bad>Good
Pain>Gain
Losses>Wins
Fear>Ambition
Risk>Upside
Embarrassment>Aspiration
COI>ROI
Miss>Hit

Short subjects still rule supreme

“Reports” beats “Automating financial reports”

“Attribution” beats “Missing attribution data?”

“Ramp” beats “Ramp your reps faster”

“Broker” beats “Quick question about your freight broker” 

“Breach risk” beats “Reduce breach risks without adding more tech”

“Completion rates” beats “When training completion doesn’t result in behaviour change” 

These accurately label the email without being deceptive or screaming “SALES/MARKETING - DELETE ME!” 

Email volume has trained prospects to instinctively ignore sales/marketing noise

Remove data points that get your outreach categorized without any thought

“You’ve got 2 or 3 decent options”

That’s one of the most valuable things a seller can say right now

Buying ANYTHING is a nightmare (Whether it’s a payroll solution, creative agency, or a pair of jeans)

Every market is flooded with options
Every category & product seems to overlap
And everyone claims they’re the best

So buyers get overwhelmed and do what overwhelmed humans always do… Nothing 🤷‍♂️ 

And yet sellers still act like their product is the only possible solution on Earth

Which is either bias, fear, or delusion

Your buyer almost certainly has looked or will look into competitors

So stop avoiding it and handle it head on

The job of a modern seller isn’t to pretend alternatives don’t exist, it’s to actually understand the buyer well enough to help them choose

(Even if that choice isn’t you)

“Based on what you told me, there are probably 2 or 3 ways to tackle this…

Option 1 makes sense if your main goal is X
Option 2 works better if Y is the real fire
Option 3 only makes sense if Z is already true”

That doesn’t kill deals it creates instant trust and helps the buyer make sense of things 

Because now you’re not forcing an outcome, hiding information, or pushing a commission-first agenda

You’re helping them make a less risky decision for their situation

And funny enough… that’s when buyers stop guarding themselves and let you help them

(Inspired by the lady in Marks Clothing telling me I should probably get Slim/Straight leg Levi’s in a black/dark blue wash)

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