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.

We bought our first home in 2020 while I was making CAD$50K/year and my partner was serving tables for minimum wage

One month later, I hit quota, then I hit it again, and again.

And suddenly I found myself with the financial, emotional, and physical space to focus on other "less important" things

Like creating goofy videos on TikTok/LinkedIn

It was the first time in my adult life I felt like I had a real footing

That house is where I filmed over 1,000 videos, wrote a book, became a dad (again), accepted two job offers, quit three jobs, and launched my business

It's where I spent the last few months rebuilding everything when all I thought I knew to be true about my life fell apart 

It was a dream home, not because it was fancy (trust the 37 viewings it took to sell)

But because it met my family's needs and then some... with the bonus of a very low 2020 interest rate.

When your basic needs are met, your brain stops running on survival mode and starts focusing on more inspiring questions like:

- What do I want to build?
- What kind of parent do I want to be?
- What funny/helpful thing should I create today?

Yesterday we handed the keys over and walked out of that house for the last time

It felt like closing a chapter, not a fairytale chapter, one with grief and loss and growth and some very questionable attempts at DIY 

But a chapter that made all this possible *gestures randomly around*

So instead of flexing the huge mansions, sexy sports cars, and tropical vacations that people tend to post about online

Here's to what really matters in life: stability

The kind that lets you show up as yourself, take risks, and get a little closer to the life you want ❤️

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.

Product? ✔️ Price? ✔️ Buyer? 👻

If a buyer says “yes” to everything except buying, it means you never found a real reason for them to care

Because people don’t buy products, they don’t buy features, and they don’t buy because of low prices

They buy problem resolution

No problem -> no impact -> no urgency -> no decision

Gap Selling 101: The problem drives the sale, not your pitch or the customer's criteria

If the buyer can’t articulate what their current state is costing them and you haven’t helped them diagnose it (or pushed back on their lack of a problem)

Then they have zero reason to change, zero reason to move, and zero reason to buy

When deals go dark, it’s not the close, the negotiation, the demo, or the product that broke

It’s almost always the discovery (or lack thereof)

Identity theft is not a joke, Alfie! 

"Can I copy your homework?"
"Yeah just change it up so it's not obvious you copied"
The homework...

Spot the difference (level: Impossible)

Sales Feed from Temu

*Spider-man pointing meme*

"Mom, can I have Will Aitken?"
"No - We already have Will Aitken at home!"
The Will Aitken at home...

If I suddenly start acting differently/suspicious on here, it's highly likely that Alfie's unalived me and has begun wearing my skin as a disguise

Can't even tag him because LinkedIn removed his profile after his AI automation tool broke their terms of service 😂

I’ve lost more 3 times as many deals as I have won

But the ones that hurt the most?

Are the deals I should’ve killed months earlier

Inflated forecasts, wasted time & energy, and missed opportunities I could've been focused on generating elsewhere

Here’s 6 ways to lose faster and cleaner:

1. Disqualify early

If there’s no real problem… you're not a good fit to help them solve their problem... or the person can't/won't buy…

Then you’re not in a sales cycle, you’re in story time

I can watch 10 minutes of a rep’s intro call and tell you if the deal’s going to close or not

Most reps can’t see it themselves, because they’re high on hopium.

Be curious, skeptical, and protect your and your customers' time

Ask "Sounds like you'd be fine if you didn't address this problem, am I missing something?”

2. Make it easy for them to say “no”

That deal aging in your pipe like it’s from the Industrial Revolution?

Channel your inner Elsa and "Let it go"

Remove the sales pressure and leave space for honesty

Ask “Seems like this isn’t a huge priority, is that fair?”

3. Understand the real reason you lost.

“They chose a competitor” isn’t the reason you lost, it was just the outcome of the reason you lost.

Why did the competitor win?
What did they do earlier, better, or faster?
What did you miss that would've allowed you to disqualify earlier? 

Ask “Promise I'm not going to try to change your mind, I’d just love to understand what led you to that decision"

Don't let your failures go to waste, learn from them. 

4. Ask for a referral

Especially in no-decision land if you've done a good job and built trust in the sales cycle then you should always see if there's a referral to be had

Ask “Totally get the timing is off. Don't suppose you know anyone like yourself who could be dealing with [problem]?”

It’s shockingly effective, likely because the prospect feels guilty 😂 

5. Send a "thank-you"

Shoutout Samantha McKenna who writes handwritten thank-you notes to closed-lost deals

Not because it’s cute (which it is), but because it’s memorable

And when the new vendor screws up? When that problem they didn't solve rears its ugly head again?

Guess who gets the callback? Samantha McKenna does. 

6. Set a check-in date

Problems grow, priorities shift, and competitors fumble

Ask “Okay I'll leave you it it and cheer you on from the sidelines, mind if I check in six months from now to see how {thing} has progressed?”

Turns today’s “no” into tomorrow’s pipeline


Stop fearing the L, a clean no with future opportunity is worth 10x more than a messy maybe ✌️

"I’m blind, I can’t drive" Sounds like you’re lacking VISION!
“I’m a man, I can’t get pregnant” Have you even tried?!

Motivational videos have officially gone off the rails

But if you need a "No Excuses" hype video to perform in sales… you’re probably already losing

The actual winning mindset? It’s not superficial motivation, short bursts of energy, or drinking the company Kool-Aid

It’s the removal of EGO.

Ego blocks reflection, kills learning, and shuts down curiosity

“I already know everything”
“I don’t need to improve”
“It wasn’t my fault”

Nope 🚫 No one wants to be that rep

As we close out 2025 this is the perfect moment to strip ego out of the equation and actually look at our years with clear eyes:

- Your FAILS: What broke? Why? And what behaviours/processes need to change so it doesn’t happen again?

- Your WINS: What worked? What decisions or habits created them? Double down

- Your PLAN: Realistic goals, clear processes, and routines that make 2026 the year you operate at a higher level vs. just hoping for it

This matters in business and in life, it all compounds

Today, Lindsay Rios is joining the LAST Sell Better Daily Sales Show of 2025 to walk through the exact post-mortem process she uses with clients to build momentum

If you want to walk into next year swinging, not guessing, jump on with us at 12pm ET https://hubs.la/Q03T62XN0

Just did the math and I’m getting ~40% pickup rates on cold calls when calling from my mobile phone*

Here’s why I (and ChatGPT) think that is… 

A couple of people have picked up and said “Will?”

The first time I was confused and asked how they knew it was me calling

Apparently their phone said “maybe Will Aitken” 

So it’s a cheeky caller ID + brand combo

Important notes:

- Using very solid contact data (multiple tools) and only call mobile numbers

- Calling people in North America with a Nova Scotia area code, bit of a pattern interrupt as only 22 people live in NS

- I’m known to most the people I call from LinkedIn engagement/following, yes it’s a little bit of a cheat, but it’s also just smart to focus on the leads who are likely to be familiar w me first

- I have typically emailed them from the email address that’s connected to my Apple ID, which also has my mobile number in the footer, I think iPhones are doing some background dot connecting here. Maybe I’ll ask the Geniuses next time I’m at the mall

- I’m not doing high volume, the most calls I’ve made in a day since doing A Sales Growth Company has been 16 (Forgive me sales gods, I promise to step it up in Q1)

- I’m objectively hotter than most people. So perhaps that’s another pro tip for outbound, sex appeal > relevance**

Anyone else tried cold calling from their cell instead of a Dialer/VOIP?

I’ve heard of teams using a CNAM registration for businesses, but I think that can hurt as much as it helps. Looking at you Scotiabank, I don’t want a credit card.

Warn me if I am going to call my kid’s daycare and appear as “Spam Risk”

* ~40% means 36.5% rounded up for a better hook

** You must be 6ft4, have ocean blue eyes, and speak with an accent North Americans find “cute” for this particular play to work

Your Offer-to-Ask Ratio probably sucks 👎

Something Keenan hit on in Gap Selling

Something we’ve hammered home even harder in Gap Prospecting.

Is what you’re offering worth SUBSTANTIALLY more to your prospect than what you’re asking for?

The problem is most sellers (and most teams, let’s be honest) have no clue what their buyers actually value

Example of a bad offer-to-ask ratio:

“I’ll give you a demo in exchange for 30 minutes of your time”

You’re offering to show them the same thing they’ve already seen on your website, in your competitor’s emails, and in the 14 ads your marketing team already hit them with

And in return you’re asking them for 30 minutes?! 

Maybe that doesn’t seem like much to you, but for an exec 30-minutes is hundreds of dollars in salary + thousands in opportunity cost + the mental energy required to task switch and deal with a sales rep

That’s a TERRIBLE deal for the buyer!

So what do you offer instead?

We break it down in Gap Prospecting, for something to be valuable it has to be:

- Unique (they can’t just Google/ChatGPT it)

- Insightful (teaches them something new or causes them to reflect on their current state)

- Relevant (tied to a real problem you can reasonably assume they’re feeling now)

- Low effort (easy to consume, easy to act on)

The good news is most vendors are sitting on insane amounts of insight, data, experience, industry patterns, failure stories, success frameworks, peer knowledge… 

That’s the ✨good shi✨people actually want 

And if you position those insights around the exact problem your product solves, then anyone who raises their hand is basically self-qualifying

A CFO showing interest in a benchmark for e-commerce payment failure rates is them telling you:

“Yes declined transactions is something I’m worried about/haven’t thought about enough yet”

A Director of Revenue operations showing interest in a data audit/sample is them telling you: 

“We know (or think) our data isn’t perfect” 

A Director of IT being interested in a conversation with your consultant about how other companies are preparing for upcoming legislation changes is them telling you:

“We’re not 100% convinced we’re prepared”

The segue from that to a deeper convo should be seamless

So here’s your homework:

- Brainstorm 5 new offers that are unique, insightful, relevant, and low friction (Use your internal execs, SMEs, product, CS, sales, marketing, and your customers)

- Build the content/process to make those offers slap hard (PLEASE no bait and switch with a “whitepaper” that’s actually an incognito product brochure or an “audit” that’s actually just a demo)

- Test them across outbound + marketing

Upgrade your offer
Ask for very little in return
Grow your pipeline without sending gift cards

95% of outbound teams don’t think enough about this, but it’s an incredibly easy win

If someone can answer all your questions without stopping to think, you’re not doing discovery...

You’re just letting them run their script.

I reconnected with an old uni friend of mine last week who told me they were thinking about quitting their job

They wanted advice on finding a new gig via LinkedIn and assumed I knew what the hell I was doing here (I don't 🤫)

I asked why they were looking to move company

They listed off the usual stuff: 

- No progression
- Passed up for promotion
- Not making enough money
- Feeling undervalued by their manager

They’d clearly told this story to a dozen people before... 

Every complaint rolled out instantly, it almost sounded rehearsed by this point

So I asked them:

“Wow, well you've been there for three years, so something must be good. What’s the part of this job you’d actually miss if you left?”

Silence.

They’d got so focused on why they wanted to leave, they had stopped thinking about the reasons they might want to stay

After a few seconds of pondering, they said, "Honestly? The team... and the freedom... And the fact I can switch off at 5 without taking work home to my kids, my friends who work at other agencies are all run into the ground”

And suddenly their whole perspective changed

The problem wasn’t that the job was awful

It was that a part of it was draining them and they’d let that single part overshadow everything else

Quitting wasn’t the only answer (yet)

That’s what GOOD discovery does

If someone never stops to think
If every answer is instant
If nothing forces reflection

Then you’re not helping your buyers see anything new

You’re just letting them vent on autopilot while you take notes

Real insight comes from the question that breaks the script and highlights new or overlooked information

The question they haven’t pre-loaded a response to

The question that makes them re-evaluate what the real problem is or where the real opportunity actually lies

In sales or in life, the most valuable question is the one that makes someone go quiet for a second and think “Huh... I hadn't considered that"

That’s the moment that changes decisions, not a million surface-level questions that they already know the answer to

(HINT: You'll know when you're doing this right because people will often tell you by saying "That's a good question")

Since I was a boy I’ve been made fun of by my sisters, friends, and colleagues for…

my ginormous ears 👂

But you know what ears are really good for?

Listening

We all know it’s a killer sales skill

It lets you build trust, uncover problems, and position yourself like an actual advisor, not a “demo dispenser”

I’d love to give you a cheap hack for how to listen, but you can’t fake it

People can smell fake listening like a pair of wet socks after rugby practice

But there are signs that tell us if someone is doing it well:

1. The basic stuff: nodding, expressions, eye contact, note taking, not interrupting, pausing before talking, the occasional “mmm” & “uh huh”

2. The bare minimum: recapping what they said + asking a logical next question (not the next question on your list)

3. The good stuff: recapping in your own words (✨flair included✨), clarifying what you heard, and asking deeper questions about what was said

But here’s the secret fourth level, the level epic sellers do that average ones skip:

4. Asking questions about what you DON’T hear.

Because you don’t change someone’s thinking by getting them to repeat what they already know…

You change someone’s perspective by getting them to consider what they may have overlooked

Here’s a concrete example (L&D persona)

“So Sam, just to make sure my ears are actually working today… you’ve been wrestling with this since May 2023, it’s already cost you roughly $180K in rework + drop-off, and it’s creating additional performance risk every quarter. And from what you’re saying, it seems like the root cause is a mix of outdated curriculums lingering around and an LMS that can’t support the new formats you need. Did I get that right?”

Sam: “Yes. That’s exactly it.”
(If they say this enthusiastically, congrats, you crushed levels 2 and 3)

Then you step into elite territory:

“I’m glad I heard that correctly. What I haven’t heard you mention is how this impacts manager readiness. Usually when completion rates drop this low, managers feel it first… but you haven’t brought that up. Is that not a factor here, or has that not surfaced yet?”

Watch what happens next: 

Sam goes silent 🤫 
Sam thinks 🤨
Sam reflects 🤔
Sam connects dots 💡
Sam realizes something bigger they weren’t consciously tracking 😮

“Actually… now that you mention it, we have seen a spike in new managers asking for remedial coaching. I didn’t connect it to our LMS issues, but that might be part of the problem”

That’s the moment you stop being a vendor and start being someone who helps them see their world more clearly

That’s what the best sellers do

Yes they listen for what’s said.
But they listen harder for what isn’t said.

Finance: "Did you really spend $5,000 on a trip to San Diego?!"
Sales: "Yes, but I closed a $240,000 sale as a result of that trip"

Selling in person immediately kicks your trust level up
Which gets you to the truth quicker
Which allows you to actually problem solve with real information

The difference in information density and problem discovery is INSANE

Which is why I believe that if you're not going to events, setting up on-sites, and proactively trying to get facetime with your customers.... You're leaving money on the table

Even if there are no trade shows on the horizon, you can run this play:

Pick a city/region with a high density of A-Tier accounts/prospects (bonus if it's a warm one)

Reach out to a few and say something like this:

"Steve, planning a trip to Raleigh next month. Given you're there, I'd feel dumb not asking… Any chance you’ve got 20 minutes for a coffee? Been digging into how construction teams are handling billing & project-complexity issues, with and without our help, and some of the patterns might be relevant to what you’re juggling over at MGC. Open to seeing if our calendars line up?"

Once you've booked just one meeting, sort the flights/hotel, then double down on the follow-ups so you can stack your calendar with coffees, lunches, and dinners

Cost shouldn't be a roadblock for the quality of a face-to-face meeting with an ideal fit buyer (even if finance gets grumpy about it)

Remember folks sandbagging is BAD ⏳

Unless of course the penny pinchers in upper management haven’t included any incentive for you to overperform

Because we can’t have salespeople making too much money now can we?! 😱

If that’s the case, here’s 8 ELITE sandbagging tips to “hypothetically” get away with it

1. “Legal review is taking forever”

Reword “I’m sandbagging this deal” into “Our legal team is being extra thorough this quarter”

Every time there’s a revision, let it sit in your inbox for two days, then use a Slack thread to communicate each redline

2. “Let’s wait until your Q1 budget refresh”

The buyer’s ready & you’re ready

But you care about their fiscal strategy because you’re a thoughtful and customer-centric seller

Also, congrats you’re now a CPA

3. “Just want to make sure this implementation doesn’t interfere with your holidays”

Look at you being considerate again! 🥰

Would be awful to disrupt their workflow with an onboarding in December

With this line you’re basically Santa Claus 🎅 

4. Use my Slowroll™ Email Template

Subject: “Just looping in some more people”

Body: “Before we finalize anything, I want to make sure we’re set up for post-sale success. 

As such I’d like to suggest we introduce your IT Director to our Head of CS prior to moving forward. 

It’s worth taking an extra beat to make sure this supports your broader IT infrastructure and security requirements.”

5. Become deeply committed to mutual action plans

“We need to align all stakeholders to reduce post-sale risk” 

No you don’t.

But this gives you 4 more steps to schedule, one a week until, you guessed it, January!

Pro-Tip: Suggest your company fully roll out a deal room solution to aid with this

6. Purposefully misenter & leave files out of the procurement system

“Oh, you use Coupa? That’s perfect because I know exactly how to get this thing to auto-deny by adding spaces to our HQ’s ZIP code”

7. Invent a “shadow forecast” tier

Tell your manager it’s a “stretch deal.”
Tell the VP it’s a “50/50”
Tell RevOps it “ghosted”
Tell your CRM it “doesn’t exist”
Tell your bank account “it’s coming Jan 3rd”

8. Introduce the exclusive “New Year Promo”

It’s not a discount, it’s just the same offer in January with a sexier name

Marketing will thank you for your creativity

I just analyzed 10,000 posts from the top 50 sales creators on LinkedIn

Here's what the data says...

Notable: Even when looking at just the top 1% creators, their average engagement is down 9% since this time last year

Before the comments turn into a TED Talk on statistics, this is correlation, not causation

It’s “on average" not “gospel truth”

For example, if you make a great video, you can absolutely dunk on a mediocre text post

Still patterns are patterns, so I put the clearest trends (the ones that held up statistically) into the carousel

Ping me a DM if you want to play around with the data/GPT yourself

Insights from over 10,000 LinkedIn posts

“Never open your mouth until you know what the shot is.”
- Ricky Roma (Glengarry Glen Ross, 1992)

Most sales teams get taught a version of this

Understand the reason behind the objection/question before you answer it, allowing you to gather more information, understand the need/problem, and avoid stepping on a huge landmine

Good advice… until reps butcher it

Because when you do it wrong, it doesn’t feel “consultative”
It feels avoidant, combative, and a little smug

Example of the bad version:

Buyer: “Do you have this feature?”
Seller: “What makes that feature important to you?”

Congrats, you just turned a reasonable question into a f*cking hostage negotiation 😂 

Buyers hate this because it signals you’re dodging them or playing games

Here’s the right way to do it:

1. Acknowledge
2. Answer lightly
3. Bridge into diagnosis

(AAB if you want an acronym to post-it to your desktop)

Buyer: “Do you have this feature?”
Seller: “Yeah, we have ways to accomplish that. How useful it is depends on how you’re trying to use it. What were you hoping that feature would help you avoid or fix?"

You answer with something so they feel respected, then you zoom out to understand the real reason they asked before diving into the deeper explanation.

Same with price:

Buyer: “How much does it cost?”
Seller: “Most teams your size land somewhere between 1k and 10k a year. I can get you exact numbers; it just depends on what you’d actually need. Got to imagine there's something that made price the first thing on your mind, was this something you looked into in the past but it was too pricey, you've anchoring against other vendors, or something else?”

The moment you stop acting like their question is an attack, the whole vibe changes

Answer the surface-level thing so you don’t trigger their defences

Then work your way to the need behind the question like an adult, vs. a slithery little sales snake that's a pain in the ass to work with

Problems over solutions (duh)

But here's where people STILL go wrong

They position the "Problem" as the absence of their solution

Your buyers don’t care that they don’t have your solution because that’s not a real problem they can see and feel today

If your company & its competitors vanished tomorrow (e.g. Electric Vehicles)

Your potential buyer’s problem would still exist (e.g. Gas Prices & Pollution)

That’s why focussing on “the absence of your product” rarely resonates

Because nobody wakes up thinking:

“Darn, I don't have a Tempur-Pedic mattress”
"Why don't I have solar panels on my roof yet?"
"If only we had a centralized place to store all our content"

They wake up thinking:

“Damn, my back feels like it got hit by a bus”
"Wow I had to dip into my savings to cover our electric bill"
"Where the hell is that channel partner slide deck?!"

See the difference? One is your world, while the other is their reality

The absence of your solution is not a problem they can relate to.
The root causes & impacts of their pain is.

Here's an example of how to create intrigue/curiosity with a custom offer in your outbound campaigns

Try to think about ways in which you can create irresistible offers like these based on what you sell

Here's some examples:

Sales Training (ASG) - Sequence Feedback/Scoring
Social Media Platform (Sprout Social) - Employee Advocacy Heatmap
E-commerce (Shopify) - Conversion Audit
Customer Service Chat (Zendesk) - Response Time Test
ATS/Job Ads (Greenhouse) - Candidate Experience Test
Billing Tools (Stripe) - Revenue Leakage Estimate
Lead Routing (Chili Piper) - Booking Experience Stress Test

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