Will Aitken

A Sales Growth Company

Heading up outbound sales & GAP Prospecting training

General Manager Prospecting Practice

WillAitken.com

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

Chief Vice Directing President of Managing Things

Sales Feed

B2B Sales Media company Sales Feed

We make content that helps sellers sell and brings a big ol'd smile to their face when they need it most

Co-Founder

Sell Better 

I'm one of the hosts of SellBetter's epic daily sales shows

Host

Lavender

Head of Social

Head of Content

Evangelist

Proposify

Senior Account Executive

Account Executive

HR.com

Preacta

Recruitment Consultant

Search It Local

Sales Representative

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.

24hrs with a Jen Allen-Knuth neck tattoo:

- Immediately improved my close rate by 15%

- Kids were initially confused but have now accepted their new sibbling

- Their school teachers haven’t said anything, but I can see by their faces that they’re impressed 😎

- Only two texts following yesterday’s live stream saying “dude what’s on your neck?”

- Didn’t wash off in the shower this morning

Is this Challenger Sales yet?

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.

What if we handled trick-or-treaters like software buyers? 🎃 

Business buyers conduct more than 70% of their research online before ever speaking to a sales rep (Forrester)

Storylane lets you give them a taste of your candy (product) before they're ready for a sales conversation

#ad #halloween

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

A Neck Tattoo?!

After 6 head-to-heads on Will vs. Jen we were left with a tie.

So the winner was decided by a popularity contest - Which I lost 😞

So here's my punishment: a temporary tattoo of Jen Allen-Knuth's face on my neck.

I get to wear it on work calls, when picking up my kids from day care, and on the live show I have planned for later today.

Thanks, Close team for picking such a lovely photo of Jen!

"TAKE YOUR SHIRT OFF AND STOP J*CKING OFF ALL DAY"
- Andy Elliott 2025

My recent YouTube video reacting to viral sales clips on IG Reels taught me one thing... 

Algorithms reward weird ass behaviour.

I promise that if you come to A Sales Growth Company for sales training, you're allowed to keep your shirt on the entire time ❤️‍🩹

🔥 ROAST my Discovery Call 🔥 

I judged a "Discovery Competition" at Salman Mohiuddin's Sales Sprint event this week

6 Sellers had 7-minutes to complete a discovery call with the bot that the team at Hyperbound uses as part of their Account Executive hiring process

Myself, Jen Allen-Knuth, and Eddy Bahnam then gave each seller feedback on what they did well with and how they could improve

I HATE giving feedback to strangers 😂

Coaching is intimate, and without knowing someone, their style, and how they like to be coached, you can end up sounding like a critical w@nker

As Babe Ruth said “The loudest boos always come from the cheapest seats.”

So I thought it'd only be fair if I also gave the challenge a spin and let strangers (that's you folks on LinkedIn) judge my performance

Naturally, I'm using GAP Selling so Keenan can judge me hardest 😉 

*note I went over the 7-minute time limit*

Discovery needs to uncover 3 things:

BUSINESS PROBLEM: something costing the business time, money, or opportunity

ROOT CAUSE: the “why” behind the problem, what’s actually broken and what your product will need to solve for

IMPACT: the downstream effects and why leadership might give enough of a crap to change 

⸻

Yesterday I had the joy of judging a discovery competition with one of Hyperbound’s AI bots at Salman Mohiuddin’s Sales Sprint ‘25.

In this scenario, the bot played a VP of Commercial Sales at Figma (IPO in 2025).
A Hyperbound BDR had booked the intro call.

Here’s how a discovery could’ve gone if the rep was running GAP Selling:

⸻

*After quick rapport & agenda*

Rep: “Brandon, I saw in Figma’s IPO release a big goal was to expand use cases across departments. How much of a focus is that for the commercial sales team?”

Brandon: “Yeah, we’re selling into a few new personas for the first time. Traditionally it’s been design departments.”

Rep: “How’s the team handling that change?”

Brandon: “Honestly, not great. The sellers are struggling to understand the motivations of these new personas.”

Rep: “What makes you say that?”

Brandon: “Feedback from reps. Conversion rates with new personas are lower than average. We’re trying to enable them more.”

👉 BUSINESS PROBLEM identified.

Rep: “When you say ‘enable them,’ what does that look like?”

Brandon: “Managers are reviewing calls, doing training sessions, role plays… practice makes perfect.”

Rep: “And how helpful has that been so far?”

Brandon: “It’s inconsistent. New hires especially struggle. Managers just don’t have enough time to coach.”

👉 ROOT CAUSE uncovered.

Rep: “So coaching’s happening, but managers are stretched. When you say conversion’s down, how much exactly?”

Brandon: “We’re at 17.5% with new personas, historically it was 33.5%.”

Rep: “So you’re closing at half the rate. And these new personas, how much of your pipeline do they make up?”

Brandon: “About half.”

Rep: “Got it. If your FY new business goal is $30M, half from new personas… you’ve got roughly $7.5M at risk if that gap doesn’t close. Fair ballpark?”

👉 INTIAIL IMPACT (more downstream to uncover, knock-on effects, wasted outbound focus, tying back to business expectations etc) 

⸻

That’s the moment the rep earns credibility, by quantifying why the problem matters and tying it back to outcomes.

Then (and only then) is where you bridge to how Hyperbound could help reps practice new persona conversations, get feedback, and improve their skills despite their manager’s being to tied up for coaching. 

Want your team to learn how to GAP Sell? Let’s chat.

I’ve been having some fab conversations with sales leaders this past week regarding A Sales Growth Company’s team workshops and 2025 SKOs 🤘

P.s. here’s a photo of Jen Allen-Knuth with food in her mouth

Here it is folks, the worst sales advice ever given...

5 ideas to help you sell on LinkedIn (without paying for Sales Nav)

Sat in on a workshop presented by Eddy Bahnam at Salman Mohiuddin's Sales Sprint event earlier this month

(Follow Eddy for LinkedIn tips, he's the GOAT)

In that talk, Eddy shared a few creative ways to make use of LinkedIn's main site to find new leads

Including a few things I didn't know, like the job ad URL second timer 🤯 I wish i'd known that one when I was an agency recruiter

What creative ways have you found to find leads on LinkedIn?

Drop 'em below as this one will likely need a part 2

(I work with Hansel Alvarez for all my long-form YouTube content like this, hit him up if you want to grow on YouTube)

I love the smell of a takedown campaign in the morning

Outbound "pattern interrupts" have a short shelf life

They end up being gimmicks when the unexpected becomes the expected

For example, last year, someone sent me a $0.05 Venmo with a cold pitch in the note

It got my attention

But soon after two more people used the EXACT same play on me

By then, it was just irritating (especially because we don't even have Venmo in Canada 😂)

This is the problem with silver bullet advice like "Use this cold call opener" or "This subject line gets your emails opened every time!!"

It gets old and becomes a quick way to be ignored

Novelty can work as a way to get your prospect's attention (See Dale Dupree)

But only when it requires effort AND is built on a strong foundation of:

- Knowing your buyer
- Doing your research
- Focussing on them vs. you
- Creating credibility with relatable problems

(Clip from Salman Mohiuddin's Sales Sprint event)

Luxury brands don’t tell you they’re luxury. They show you.

If you’ve ever walked into a designer store (sorry for the PTSD, husbands) you’ll know exactly what I mean.

Everything FEELS expensive.

The lighting, the layout, and the carpet that probably costs more than your rent.

They introduce you to a personal advisor who says your name like it belongs on a yacht and hand you champagne. 

And when you pick up a bag? They don’t just say “yeah that one’s $10k” they tell you how many were made and what it’s crafted from

That vibe carries to the website, the airport ads, even the counter in Sears.

Everything whispers: “If you buy this, you’re doing well”

So here’s my question:

Why the fuck don’t we treat 5/6/7 figure business purchases the same way Chanel treats a purse?

Instead we get:

- Sloppy AI-written emails that read like a drunk intern fed ChatGPT their product sheet

- Green sellers who learned sales from a Google Doc last updated in 2018

- Buying processes so painful they repulse our buyers

- Websites that look like I made them blindfolded in Canva

Like… COME ON! 😂

If you're asking someone to trust you with tens of thousands of dollars ACT like it.

Invest in every layer of the experience.

Make people feel like they’re in good hands before they ever swipe the card.

That doesn’t mean faux-polished BS.

It means giving a shit about the details and thinking about how your buyer feels when they get an email, pick up the phone, are served an ad, request a demo, or decide to move forward with your solution.

My point here is that retailers sell a $10k bag better than most B2B companies sell a $250k solution.

Think about that.

How to BLOW up on LinkedIn

⚠️ I don't believe sellers need to have "personal brands" on LinkedIn ⚠️

It can definitely be helpful, especially if you sell to a Marketing/Sales/HR persona who are most active on this platform

But I'd always recommend prioritizing direct cold outreach like Emails, Calls, and DMs before I tell anyone to try be an influencer

However, I do believe all sellers should be aware of how they show up on LinkedIn

Prospects look at your profile during sales cycles and having a solid profile will improve your chances of connecting with buyers on here

Want feedback on your profile? Good news, Chelsea Olsen and I are doing live profile teardowns today on the Sell Better show at 12pm ET - https://hubs.la/Q03LRYDp0

Take back to when Dom Odoguardi interned as my personal assistant for the day

He kinda sucked and kept shoving his phone's flashlight in my face 😒 

Luckily Dom found a better calling and has just launched his own company

doContent an EGC Video Agency

EGC stands for *checks notes* Employee Generated Content!

Basically, get your team creating content to widen the organic reach of your company using the beautiful personalities who're helping build it everyday

Humor, insights, education, videos...

We know this stuff works (hence why I'm here), but it's tough to know where to start and even harder to maintain it as a company strategy.

So give Dom a call if you want help turning your company's people into brand-building machines without sacrificing their day jobs

I GAP Prospect, what do you do? 



Keenan and I will be presenting the debut GAP Prospecting training on October 29th & 30th from 12 pm - 3 pm ET

6 hours total of live, interactive, engaging and fresh prospecting breakdowns

DAY 1 (Rules of The Game)

- The nine truthbombs of prospecting
- Why modern prospecting is failing
- How to deeply understand your buyers
- How to build your value proposition around problems, impacts, and root causes 
- How to target the perfect buyers 
- The two sales that 90% of sellers miss
- How to adopt the mindset of a top prospector

DAY 2 (Doing The Job)

- How to use to refine, research, and enrich your lead lists 
- Cold calling openers and talk tracks that still work in 2026
- How to turn pushback & objections into interest
- How to write cold emails that light up your buyer's brain
- Where LinkedIn, events, mail, in-person, and referrals can add to your efforts
- How to bring this all together in sequences that get responses instead of blocks
- What causes no shows & exactly how to prevent them
- How to set yourself up for consistent success by managing your inputs


While taking part in breakouts, workshops, roleplays, and feedback sessions with Keenan and I

You'll also get exclusive bonuses like:

- Limited edish T-shirt (as shown)
- A signed early copy of the GAP Prospecting book
- 1 year access to Gap+
- 1 month access to GapUp 
- A GAP Prospecting certification
- 50 prospecting plays you can begin using immediately
- 10 AI prompts every seller should know

Learn more here: https://lnkd.in/ewhbDqUA

DM me for Qs 💚

Your mum, friend, colleague, customer, or fav celeb calls/messages you…

You’d have a conversation/reply right?

So it’s not that people don’t like getting calls/emails/dms

It’s that they just don’t like getting calls/emails/dms from random strangers who want to sell them something they don’t believe they need

This one of the things that makes outbound a challenge, the lack of familiarity

So the first place to start (and keep revisiting) when doing outbound is connecting with people/orgs who are more likely to know who you are OR know someone who you know/work with

These past few weeks working with Keenan 100% of my outbound effort has been on people who know who I am, know who Keenan is, or know someone that either of us have worked with 

As such I’ve been able to book an average of 1 meeting a day with about 1-hour time investment

So here’s where to look (and keep looking) if you want to have slightly warmer conversations:

Your network
Your exec’s network
Past closed-lost deals
Your customer’s network
People who follow your company
Past users/buyers who have moved 
Users of a product you partner with
Folks who replied to emails in the past
Competitors of your existing customers
Marketing engaged (webinars/downloads)
Companies who share investors with yours
People who have engaged with your content

Any of these make you/your company less of a stranger to that person

You can then bank that familiarity and use it as a way to build intrigue & paying attention to the problem without having to rely on creativity/deep research/gimmicks

Examples: 

Looks you and [customer company] both use [shared tool/agency/partner], they recently tackled [problem] in a way I figured might be helpful to you too. Worth a chat? 

Or

Saw you moved over to [new company]. We didn’t work directly together at [old company], but you may have seen some of the work we did addressing [challenge]. Is that [problem] something you’ve spotted at [new company] too?

Or 

Saw you grabbed the problem ID chart from GAP Selling, hope you’re enjoying the read! Curious if you can relate to the part about reps getting commoditized by weak discovery or too much product pitching? Happy to share some easy ways leaders have got their reps asking better questions to avoid this if so.

Here's a good example of "public prospecting"

Something I think many people could be doing on LinkedIn, creating outbound posts that spell out:

- The research you've done
- Insights you have for your buyers
- Strategies you are confident would work

Then tagging in a few of your key accounts so they see the post

This is one way with content consulting, but I've seen it done well with:

- Posts sharing insights/data/benchmarks from market research vendors tagging in specific R&D, Marketing, & Product leaders at relevant industry leading companies

- Posts sharing examples of cold call talk tracks and cold email frameworks that use a target prospect company as the example (for example I could share a cold email framework then use a target company like Procore Technologies to apply it to an example, then tag someone like Peter Huston and ask him for feedback)

Shows confidence on your side and creates accountability on their side to respond

Helping SaaS founders build unbeatable authority and scale their revenue with YouTube.

There's a billion-dollar company called Chili Piper with 2 of the coolest CEOs out there that could be killing it on YouTube, if the just changed their strategy.

Sadly, their YouTube channel is full of product updates and corporate content that nobody really cares about.

And it pisses me off because they have a great product and one of the craziest founding stories I've seen.

The biggest problem they have right now is that their product is naturally unattractive to the majority of YouTube's audience.

So after doing something similar with Close's CEO, Steli Efti, here's exactly what I'd do with their content:

1. Switch from corporate videos to personal brand content.

We'd focus entirely on both of their CEOs, Alina Vandenberghe 🌶️and Nicolas Vandenberghe.

Both Alina and Nicolas have 2 of the craziest and most inspiring stories I've ever seen.

Alina, who went from living in communist Romania to moving to an entirely different country at 23, and Nicolas, who went from selling newspaper in Paris to moving the USA and meeting Steve Jobs.

But having amazing stories isn't the only reason why I'd do this shift in content.

A massive percentage of the company's pipeline already comes from Alina's post on LinkedIn.

So if it already works on LinkedIn, it'll work 10x better on YouTube where videos are longer and build more trust (and people can connect with Alina and Nicolas more).

We'd create videos like:

"How I Built a Billion Dollar SaaS in 5 Years"
or
"I Scaled 4 Companies. Here's Everything That Works"

These are 1-on-1, trust-building videos that leverage both CEO's authority and story.

2. Make sales content, not product content

We'd also actively talk about sales strategies that their ICP already care about, and connect them to AI to leverage its popularity like:

"My $100M AI Sales Process"

Then, inside these videos we'll subtly introduce routing, scheduling, and qualification (Chili piper's features) as part of the solution.

so instead of pitching the product, we're teaching sales strategy and their product becomes the natural mechanism.

I'm confident when I say Chili Piper could own the niche on YouTube in 12 months.

They just need to make the switch.

But anyways, if you found this valuable tag Chili Piper or Alina to spread the word!

Oh! And let me know if you want to see the full breakdown. Had a lot of fun making this post.

GAP Prospecting - Live Q&A

Keenan and I are going live to answer your questions about the book

"The minimum deal size for our SMB sales team is $5k"

Any guesses for the average (mode/median) deal size at that company?

You guessed it - $5k! Who would have thought?!

This isn’t a pricing/packaging issue ❌ 

If this company were to increase the minimum deal to $10k, I guarantee the same thing will happen; the new average deal will be $10k.

Sellers tend to pitch and sell the minimum viable deal by default, typically because they're not sure/confident in pitching anything else

What it all comes down to is discovery (again)

Uncovering problems, knowing what's causing those problems, quantifying the impact of those problems, and untangling what their ideal future state is

All that allows us to confidently provide the BEST recommendation instead of anchoring to the minimum SAFE recommendation

Because when you do real discovery, you stop selling what fits your price sheet/rules and start selling what will actually solve each buyer's unique problem

That’s where deal size, close rate, and trust all go up together

Usain Bolt holds the world record for the 100m at 9.58 seconds

A marathon is about 42,200 meters

42,200 / 100 = 422

422 * 9.58 = 4,042.76 seconds

4,042.76 / 60 = 67.379 minutes

So why doesn’t Usain Bolt just run a marathon in 1 hour 7 minutes?

That’s almost TWICE the speed of the current marathon world record of 2 hours! 

What an idiot!



We all know this is a stupid line of thinking right? 

So why can’t folks apply the same rational thought to “scaling” sales

If something works well the first question I always hear is “how do we scale this?” 

(A.k.a. How do we do more of this with the same/less effort)

You don’t ya lemon - it works, because it’s work.

taplio

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