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.

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 😂

Generic GTM is dead → Go to my featured section for actionable GTM insights and elevate your marketing game 🔥| Co-Founder of TACK | Creating the category of People-first GTM 👥| 13+ Years in B2B Marketing 📈

I help B2B companies build go-to-market strategies that prioritize real connection because relationships, not just reach, drive growth.

After 14 years in B2B marketing, I’ve led field marketing, demand gen, community, and influencer programs. I know what works, what doesn’t, and what’s changed.

Too many companies still treat buyers like leads. That’s not how modern GTM works.

I’ve helped 35+ B2B brands shift from transactional tactics to connection-driven growth, building scalable strategies, launching communities, running 30+ webinars, and rolling out on-demand models that replaced bloated in-house teams.

Today, I work directly with brands, founders, and marketers to build go-to-market engines that scale—without the spam.

What I do:
→ Build integrated campaign strategies that drive pipeline
→ Coach creators and brands on influencer marketing
→ Design community-led and field programs that actually work
→ Speak on GTM, content, and creator-led growth
→ Act as a fractional marketing leader or advisor

📚 Author of B2B Influencer Marketing: Work With Creators to Generate Authentic and Effective Marketing (Kogan Page, 2025)

👋 Let’s work together: DM me or visit https://linktr.ee/NickBMarketing

Nick Bennett

I've been tracking LinkedIn DM patterns for 6 years.

Not the exact numbers. But the weird behaviors people have before reaching out.

Like this guy who DMd me last week. Says he's been following me since early 2020.

Since I started posting basically.

Never liked a post. Never commented. Nothing.

Just... watching. For almost 5 years.

Then my random post about being useless despite being the CMO's favorite? That's what made him reach out.

Not my frameworks. Not my playbooks. Not the stuff I spent hours on.

The throwaway post I wrote in 10 minutes while annoyed.

"This is exactly my situation. Can we talk?"

This happens constantly.

I'll post about some GTM thing and get a DM about something completely different.

"Saw your post about ABM. BTW we need help with our entire marketing org. You available?"

Or my favorite:

"I never do this but I've been reading your stuff for like 3 years and we just fired our agency and I'm desperate."

I never do this but...

Dude, you're literally doing the thing LinkedIn was built for. Connecting with people who might help your business.

But we've made it weird somehow.

People feel guilty about reaching out. Like they're bothering me by potentially paying me money to solve their problems.

Meanwhile I'm over here specifically putting "DM me" in my headline.

The wild part is what actually triggers the DM.

It's never the post I think will drive business.

The post with 3 reactions where I admit I don't know something? Five DMs.

The post with hundreds of reactions about some framework? Cricket sounds.

Because people don't hire frameworks.

They hire humans who get their specific mess.

And they need to trust you first. Which apparently takes watching you show up for years before they work up the courage to type "hey."

Some lurker reading this has been following me since 2021. Has my posts saved. Thinks about reaching out every few weeks.

But doesn't.

Because... I don't know why actually.

Fear? Timing? Waiting for permission?

Look, half my business comes from people who finally said "screw it" and sent the DM they'd been thinking about for months.

The other half comes from people who responded to my DMs checking in on them.

That's it. That's the whole business model.

Show up. Share what's real. Stay consistent.

Eventually the right people reach out.

Not because you're the best.

But because you're the one they trust.

And trust takes time. Like, way more time than you think.

But it's worth it.

Because when someone's been watching you for 4 years, they don't need convincing.

They just need to know you're available.

15+ Year B2B Marketing Leader Turned Founder | ABM, Field Marketing & Events, Influencer Marketing & More | DM Me to Learn More

I never took a GTM course. Here's my free 17-point playbook:

Spent $0 on certifications.
Made every mistake possible.
Built GTM strategies for 50+ B2B companies.

These aren't theories. They're scars.

**THE FOUNDATION (Before You Burn Cash)**

1. Your ICP isn't "everyone who could buy." It's the 20% who buy fast and stay forever.

2. Product-market fit is binary. You either have people begging for your solution or you don't. Stop pretending maybes are yeses.

3. If sales and marketing hate each other, you don't have a GTM strategy. You have two departments playing different sports.

**THE REALITY CHECK**

4. Your competition isn't who you think. It's Excel, email, and "doing nothing."

5. Nobody cares about your features. They care about their Monday morning problems.

6. "We're like Uber for X" isn't positioning. It's lazy.

7. Your pricing model reveals your strategy. Complicated pricing = confused strategy.

**THE EXECUTION**

8. Week 1 pipeline matters more than Year 1 projections. Start with 10 target accounts, not 10,000.

9. Your first 10 customers should come from founders selling. Not SDRs. Not ads. Founders.

10. One channel that works beats five channels that might work. Pick. Focus. Double down.

11. Content without distribution is a diary entry. Distribution without content is spam. You need both.

**THE HARD TRUTHS**

12. If your CAC payback is over 12 months in B2B, you're running a charity.

13. "Enterprise ready" is what you say when you can't close SMBs.

14. Your GTM motion should be boring. Boring scales. Clever dies.

**THE MULTIPLIERS**

15. Customer success is GTM. Your best leads come from happy customers, not cold outreach.

16. Speed beats perfection. A decent strategy today beats a perfect strategy next quarter.

17. Fire fast. Hire slow. The wrong GTM hire costs you 6-9 months, not just their salary.

**The Meta-Lesson:**

GTM isn't about frameworks or methodologies.

It's about talking to customers until your ears bleed.
Then building exactly what they're already trying to buy.

Everything else is just noise.

Save your $5K course money.
Spend it on plane tickets to visit customers instead.

That's the only GTM education that matters.

Why I turn down $20K/month retainers.

Sounds insane, right?

But I've learned something after taking on too many big-ticket clients who weren't ready to change.

Money doesn't fix misalignment.

I used to chase every high-value deal. Someone waves $20K/month in front of you, you take it. That's just math.

Except it's not.

Because what they're really buying is someone to blame when nothing changes.

They want you to own their problems without giving you the power to fix them. They need board deck fodder. A line item that shows they're "doing something" about their broken GTM.

Meanwhile you're writing strategies nobody reads. Running workshops nobody implements. Sending Slack messages into the void.

I spent six months doing this once. Made great money. Delivered zero impact.

Know what that does to you?

Makes you feel like a fraud.

Because you are one.

You're not doing marketing. You're just billing hours.

These days I'm brutal about qualification.

Not "do they have budget?"

But "will they actually do the work?"

Big difference.

The clients I work with now pay less. But every single week something ships. Something changes. Something moves forward.

Real campaigns launch. Real pipeline gets built. Real revenue happens.

I can point to actual stuff that happened because I showed up and did the work.

Not strategy decks. Not frameworks. Not advisory hours.

Just marketing that works.

That's worth more than any retainer.

I'm a marketer. I do marketing. If you're not ready for someone to actually get in your HubSpot and build things, I'm not your guy.

Even if you're waving $20K/month at me.

Your best business development strategy isn't saying yes to everything.

It's saying no to the wrong things.

Especially when they pay well.

8 things I'm thankful for this year:

1. Clients who don't need 62 slides to make a decision.

The ones who've been reading my stuff for years and just want to get started. No discovery deck. No stakeholder alignment. Just people who trust me to fix their broken GTM.

2. My 4pm hard stop.

Three kids who don't care about my pipeline metrics. They just want snacks and someone to blame for the mess they definitely didn't make.

Best daily reminder that none of this matters as much as we pretend it does.

3. Building something my kids can be proud of.

I grew up watching my parents grind themselves into the ground. 60-hour weeks were normal. Being present was optional.

My kids see me close the laptop at 4. They see me say no to calls during dinner. They see work has boundaries.

That's the real legacy I'm building.

4. The lurkers.

55,000 followers. Maybe 200 who actually comment. The rest of you have been here since 2020. Just... watching.

You're weird. But you're my weird. And half my business comes from you finally DMing after 3 years.

5. Bad clients who taught me good lessons.

The ones who wanted me to own their problems without power to fix them. Who paid well but made me feel like a fraud.

They taught me that $20K/month from the wrong client costs more than it pays.

6. Constraints that forced clarity.

Not having unlimited budget. Or time. Or resources. Because when you can't do everything, you get brilliant at the right things.

My best work happens before 4pm. Because it has to.

7. Actually doing marketing.

Not strategy decks. Not frameworks. Just stuff that ships and drives pipeline.

With people who get that simple beats complex. That done beats perfect. That showing up beats showing off.

8. Teaching my kids that success isn't about the hustle.

It's about knowing when to close the laptop. When to say no. When enough is enough.

Working from home means they see it all. The wins, the frustrations, the actual work. But mostly they see that dad's office door opens at 4pm. Every day.

Maybe they'll grow up thinking balance is normal. Not something you figure out after burning out three times.

That'd be worth more than any exit.

Happy Thanksgiving to everyone trying to build something better than what we inherited.

For our kids. For ourselves. For the people counting on us to show up as whole humans, not just productivity machines.

We made it. Somehow.

I hired someone from Google once. They lasted 3 months.

Not because they were bad.

Because I hired a logo instead of a marketer.

Here's the thing about hiring:

Most companies get starstruck by the wrong stuff.

They see "Ex-Meta" or "10 years in SaaS" and stop thinking.

Like those brands are some guarantee of performance.

They're not.

I've made every hiring mistake possible. 
Hired for pedigree. Hired for industry experience. Hired for culture fit.

And missed the only things that actually matter.

Here's what I look for now:

➜ Show me what you shipped, not where you worked
I don't care if you were at Amazon.
I care what you actually built there.

One candidate showed me a campaign that generated $2M in pipeline.
At a 50-person startup nobody heard of.

Guess who got the job.

➜ Tell me about a time you had no budget
Big company marketers often struggle at startups.

Why?

They're used to throwing money at problems.

The best marketers I know can drive results with $500 and some duct tape.

If they've never had to get scrappy, they'll struggle when resources get tight.

➜ Walk me through your biggest failure
Not the humble brag version.
The real one.

The campaign that tanked.
The strategy that backfired.
The budget you burned.

Then tell me what you learned.

Because marketers who've never failed hard haven't pushed hard enough.

➜ Show me how you think, not what you know
I gave every candidate the same exercise (paid ofc lol because it's silly to require people to do unpaid work):

"Our pipeline is down 30%. You have 90 days and $50K. What's your plan?"

The best answers aren't perfect.
They're thoughtful.

They ask smart questions.
They challenge assumptions.
They think in systems, not tactics.

➜ Prove you can move fast
Marketing moves at startup speed now.

Even at big companies.

If someone needs 6 meetings to make a decision, they're dead weight.

I look for people who shipped something last week.
Not last quarter.

The harsh truth?

Your industry experience is overrated.
Your big company background might be a liability.
Your certifications mean nothing if you can't ship.

What matters:

Results you can prove.
Problems you've solved.
Speed you can sustain.

Stop hiring resumes.

Start hiring proof.

20 year reunion tonight. Class of 2005.

We're old AF.

20 things from high school (2001-2005) my kids will never understand:

1. Burning the perfect mix CD. 3 hours for 18 songs to flow just right.

2. Your AIM away message being your entire personality. ~𝘉𝘳𝘉 𝘨𝘖𝘪𝘕𝘨 2 𝘵𝘏𝘦 𝘔𝘢𝘓𝘓~

3. Waiting for your crush to sign on. That door opening sound still hits different.

4. Calling someones house and asking their parents if they were home. Pure terror.

5. T9 texting under your desk. Typing hey without looking: 4-4-3-3-9-9-9.

6. Racing home to catch TRL. Voting 100 times to keep your video at #1.

7. Downloading one song on Limewire. Three hours later: definitely wasnt a virus.

8. Your MySpace Top 8 causing actual drama. Moving someone from spot 3 to spot 7 = social murder.

9. Disposable cameras at school dances. Wait a week to see if any photos turned out. They didnt.

10. MapQuest directions printed out. Miss one turn and youre lost forever.

11. Blockbuster Friday nights. All the good movies gone.

12. Wearing your basketball shorts over your regular shorts. Fashion genius.

13. Popped collars. Sometimes two at once. Dark times.

14. CD player skipping every bump. AA batteries were currency.

15. Passing notes folded into impossible origami footballs.

16. LiveJournal posts that were just public therapy sessions.

17. Recording songs off the radio. DJ talking over the intro ruined EVERYTHING.

18. Razr flip phones. That satisfying SNAP when you hung up.

19. Facebook requiring a college email. So exclusive.

20. Actually wondering what people were up to. No updates. Just mystery.

My oldest thinks Im ancient.

Wait you couldnt just text them?
You had to REWIND movies?
The internet made noise?

They'll never know getting kicked offline because mom needed the phone.

Or fitting your whole life into 160 characters.

Or memorizing every word to that Eminem song because what else was there to do.

Tonight I'll see people I havent talked to since we thought Xanga was the future.

We'll pretend we havent been Facebook stalking for 15 years.

Someone will bring up that kid who burned a CD of just Who Let the Dogs Out 18 times.

We'll feel old as hell.

But man. Those were good times.

When social media meant writing on someones actual wall with a Sharpie.

When going viral meant everyone in third period knew by lunch.

When you had to actually show up to know what happened.

Class of 2005, we made it.

Even if our backs hurt now and we're in bed by 10.

No alternative text description for this image

We had every data signal imaginable. Our SDRs still couldn't book meetings.

CRM data? Check.
Intent signals? Check.
Usage analytics? Check.
Social activity feeds? Check.

47 different data sources telling us who to target.

Zero clarity on what to actually say to them.

One rep literally had 14 tabs open trying to piece together a single outreach message.

For a $250K opportunity.

Took him 37 minutes to write 4 sentences.

The prospect never responded.

I couldn't blame him.

We'd given him data overload, not intelligence.

So we built something different.

Fed all those signals into one AI model trained on:
- Our exact ICP parameters (not generic B2B)
- Our specific value props by persona
- Our actual customer language from closed-won deals

Now when a signal fires:

AI generates the message in 8 seconds.
Not generic "I noticed you visited our website" garbage.
But "Saw your team just expanded by 40% - that usually means [specific challenge we solve]."

Personalized to their exact moment.
In our voice.
Through their preferred channel.

Old way: 37 minutes per message. 2% reply rate.
New way: 8 seconds per message. 18% reply rate.

Our SDRs went from sending 15 messages a day to 150.

With 9x better response rates.

Not because they got better at writing.

Because we stopped making them cosplay as data scientists.

The truth about AI in GTM?

Generic AI is worthless.
"Personalization at scale" is an oxymoron.

But AI trained on YOUR:
- ICP patterns
- Messaging frameworks  
- Customer language
- Conversion data

That's not artificial intelligence.

That's amplified intelligence.

And it's exactly what Common Room enables with RoomieAI Spark.

Your data. Your voice. Your way.

Not another generic AI tool.

A GTM motion that actually sounds like you.

Just 100x faster.

#CommonRoomPartner

Having 3 kids completely changed how I work.

And doubled my output.

Every day at 4pm, I close my laptop.

Childcare ends. Three kids. Just how it worked out.

You'd think that would limit what I could build.

Instead, I'm working on the best projects of my career.

Here's what nobody tells you about constraints: They don't shrink your impact. They multiply it.

Before kids: I was the guy who'd take any meeting. 7am? Sure. 6pm on Friday? Why not. Weekend strategy session? I'll bring coffee.

Now: 4pm hard stop.

No explanation. No apology.

Just "Gotta run."

You know what happened?

I started shipping twice as much.

Because those constraints forced me to figure out what actually drives results.

Used to spend 3 hours going back and forth on a strategy doc. Now I write it in one pass and ship it. Done.

That "let's brainstorm" meeting that always ran over? Killed it. Send me your ideas in Slack. I'll tell you which ones we're doing.

Those "quick syncs" everyone loves? Dead. If it's not worth a real meeting, it's an email.

Actually, it's probably not even an email.

I work on more interesting projects now than I ever did with unlimited time.

Why?

Because I can't afford to waste a single hour on nonsense.

No politics. No process for process sake. No meetings about meetings.

Just pure execution on stuff that matters.

Maybe once or twice a week I'll jump back online at 9pm after bedtime. Handle whatever needs handling. Usually takes 30 minutes.

But that's strategic, not reactive.

My clients don't hire me for my availability.

They hire me for my clarity.

When you work till 4 you get crystal clear on what moves the needle.

When you can't do everything, you get brilliant at the right things.

I'm working with companies I couldn't have dreamed of two years ago.

Building strategies that actually ship.
Creating content that drives real pipeline.
Fixing GTM problems everyone else just talks about.

All before 4pm.

Because at 4pm sharp, someone needs a snack, someone needs homework help, and someone definitely needs a bath because... I don't even know what that is on their face.

And honestly?

That mystery substance is usually the highlight of my day.

The old me thought success meant being always on. Thought I was crushing it because I answered Slacks at 10pm.

What was I even doing?

The new me knows success means being fully present.

Present for the work that matters.
Present for the people who matter.

No overlap. No guilt. No compromise.

Okay, sometimes guilt. Like when I'm on a call and hear absolute chaos upstairs. But whatever.

Having 3 kids didn't limit my career.

It taught me what a career should actually look like.

And it looks nothing like what I thought it would.

We rolled out new pricing that should've doubled deal velocity.

A week later, reps were still pitching the old prices.

Not because they missed the email.

Because finding the new pricing meant:
- Digging through 3 Slack channels
- Opening 2 Notion docs
- Navigating a 17-tab spreadsheet

One rep literally asked a prospect to wait while he searched for the right number.

On a $180K deal.

The prospect hung up.

I wanted to scream.

But honestly? I couldn't blame the rep.

I'd buried critical information in a scavenger hunt.

And expected him to find it mid-pitch.

That's when we implemented Tango.

Now when we update pricing:

Click through the new model once.
Tango captures it.
Lives right inside Salesforce.

Rep opens an opp? New pricing is there.
Builds a quote? The process guides them.
No searching. No guessing. No "hold on, let me find that."

Old way: 3 weeks for adoption.
With Tango: 48 hours.

In Q4, we changed pricing 3 times.

Each time, instant adoption.

Not because we trained better.

Because we stopped making reps think.

The right information just appears when they need it.

That's not enablement.

That's automation.

And it's exactly what sales teams need.

Stop making reps hunt for information.

Start putting it where they already are.

Tango → tango.ai

#TangoPartner

B2B marketers don't fail at ABM because they lack data.

They fail because they forget buyers are human.

I watched a team spend $400K on intent data platforms last year. They knew exactly which accounts were showing buying signals. Had all the tech stack anyone could want.

Six months later? Zero pipeline from their ABM program.

I remember sitting in their QBR thinking, what the hell went wrong?

They'd done everything by the book. Premium tools. Clean data. Account scores updated daily.

But they treated those accounts like logos on a spreadsheet. Not buildings full of people trying to solve actual problems before their boss asks why nothing's working.

Look, I get it. We love our tech stacks. Drop six figures on ABM platforms and feel like we've accomplished something. But buying the Ferrari doesn't mean you know how to drive it.

And slapping someone's name on a PDF isn't personalization. Neither is changing the logo on your landing page. I've watched reps send "personalized" emails that were just mail merge fields. Buyers see right through that crap.

The worst part? Marketing runs these elaborate ABM plays while sales is doing their own thing. I've seen this movie a hundred times. Marketing celebrates engagement metrics. Sales ignores the leads. Everyone points fingers at the quarterly review.

One team I worked with started with 500 target accounts. FIVE HUNDRED. They had generic plays, spray-and-pray outreach, zero focus. By month three they couldn't even remember why half the accounts were on the list.

You know what actually worked?

Starting with 5 accounts. Actually talking to people at those companies. Understanding what triggered their search. What would make their CFO approve budget. What internal battles they were fighting.

Then building moments that mattered to those specific humans.

Not impressions. Not awareness campaigns. Not another bloody nurture sequence.

Real conversations about real problems.

ABM isn't about the accounts you target.

It's about understanding why those accounts would ever give a damn about you.

That's not a tech problem. That's a behavior problem.

And until you solve for that, you're just another marketer with an expensive list of logos and a pipeline that won't budge.

Stop chasing accounts.

Start understanding the humans inside them.

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Will Aitken

Nick Bennett

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The Battle

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Nick Bennett

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Likes

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