Co-Founder & Chief Revenue Officer at Sales Assembly | Developing the GTM Teams of B2B Tech Companies | Investor | Sales Mentor | Decent Husband, Better Father

I’ve spent my career trying to solve one puzzle: how do you scale sales teams without losing what makes them great?

Before Sales Assembly, I lived the highs and lows of hyper-growth - leading revenue teams, juggling targets, and realizing that growth without structure eventually collapses under its own weight. The lesson stuck: great teams don’t just grow fast, they grow well.

That’s the idea behind Sales Assembly. We built the preeminent skill development platform for B2B tech companies: part training, part community, part therapy for GTM leaders trying to do more with less. We help teams move faster, stay aligned, and actually enjoy the process of getting better.

Somewhere along the way, I also became a General Partner at VentureOn Partners, Chapter Head at Pavilion, and mentor with Techstars. I’ve spent a lot of time with founders and operators who are chasing the same thing: building something that lasts without taking themselves too seriously.

A client and friend once described me as someone who “builds community through authenticity,” which I’ll take as the polite version of “tells it like it is.” That’s probably fair.

Outside of all that, I’m a decent husband, a better dad, and a walking Simpsons encyclopedia (seasons 1–11 only, of course). I travel when I can, laugh often, and still believe a good team - and a good joke - can get you through just about anything.

Matt Green

Spoke with a guy launching a company in stealth. His entire outbound strategy has been hundreds of handwritten notes. 6 months in, they're deploying ten Fortune 500 clients.

Not emails. Not LinkedIn messages. Not AI-powered video prospecting.

Actual handwritten notes. With a QR code to book time. Mailed to every executive he'd ever worked with.


Sounds bonkers, but actually makes perfect sense. I mean, I get that it's 2025. Sure, we have AI that writes perfect emails. Sequences that personalize at scale. Prospecting tools that know what cereal your buyer ate for breakfast.

But the gangster move is a stamp.


He told me what happened at dinner that kicked off his whole strategy.

He's breaking bread with an old contact. CRO of a $12B company. 3,000 employees. The exact buyer every SaaS vendor is chasing.

My guy mentions he's been emailing him. Ten times over a few months. Zero response.

The CRO laughs. "Oh, I don't read my inbox anymore. Just email my chief of staff if you want to get a hold of me."

Not "Sorry man I'm swamped." Not "Shit I think it went to spam."

He literally doesn't open his inbox. Ever.


Here's what's wild about this moment we're in:

We've spent three years building AI that writes better emails, crafts better subject lines, personalizes at scale. Meanwhile, the entire ENT buying committee has collectively decided to ignore ALL of it.


Every inbox will be perfect in 12 months. Every email will look hand-crafted. Every message will reference that podcast you were on or that article you wrote.

Which means every email will still be just noise. It'll be "better" by today's standards, but noise nonetheless.


But a handwritten note? That's a human being who gave a shit for 90 seconds.

That CRO gets 847 emails a day. 840 of them are vendors who "noticed he recently raised a Series C" or "thought his CEO's comments on the last earnings call were really compelling."


AI didn't kill email outbound. AI made it so good that everyone's doing it. 

Which is what killed it.


There's a huge shift right now going back towards relationship selling. It would be a bit romantic to think it's because it's noble or pure.

But in reality, we're going back to it because AI made everything else worthless.


Handwritten notes. Showing up at the conference. Actually knowing someone before you try to sell them something.

Sure, old farts like me might think it's romantic. But at the same time, you can also just consider it math.


When everyone can send a perfect email, nobody's reading email.

And yeah, the kinda stuff this guy did is harder. That's why it works.

CRO of Sales Assembly | Decent Husband, Better Father

Jen Allen-Knuth

Founder, DemandJen | Sales Trainer & SKO Keynote Speaker | Dog Rescue Advocate

I help B2B revenue teams stop losing pipeline to buyer status quo. I'm a former Enterprise seller who carried quota for 18 years, closing 7-figure deals with Fortune 500 brands. Now, I run DemandJen, a sales-training firm trusted by Autodesk, GE, G2, IBM, Bloomberg, Instructure, Sprout Social, and more.

From conference stages to company Sales kickoffs, I'm known for:

- Buyer-Centric Frameworks – Practical playbooks for defeating buyer status quo in outbound pipeline generation, running executive-level discovery, building a point of view on cost of inaction (COI), and gaining consensus with larger Enterprise buying groups. 

- Story-First Messaging – Techniques that replace product pitches with problem-centric narratives that buyers remember.

- Engaging Delivery – A direct, humorous style that keeps even your most tenured reps taking notes.

Featured in Forbes, Sales Hacker, and 200+ podcasts, I combine real-world stories with data-driven insight to move audiences from inspiration to application. When I'm not on the road, you’ll find me in the Chicago suburbs chasing my 4 rescue dogs and 4 step-kids.

Head of DemandJen

Delivering SKO keynotes & virtual workshops that won't put your teams to sleep.

B2B Sales & Marketing teams have tried to earn buyer time and attention with a strategy of "more". 

More dials.
More emails.
More content.
More "value" and ROI.

But, 2023 showed us "more" is expensive and no competition against today's risk-averse B2B buying teams.

Instead of motivating the team to do “more”, I help empower teams to defeat customer status
quo and to make their sales conversations a competitive advantage.

AMs and AEs - try this.

Pick a customer or prospect who recently bought from you and needed executive buy-in for the purchase. 

Ask them this Q:

“Would you be willing to share what visuals you used to make the business case to your CXO for this purchase?”

I used to send my prospects a 40ish page slide deck with a detailed implementation plan. 

The first time I asked a prospect this, they emailed me 4 slides. None of my 40 slides were in it.

Instead, it was:

Slide 1 - framed the business problem and “so what” 
Slide 2 -  framed how they were solving it today and what negative consequences were resulting from that approach 
Slide 3 - alternative solutions they explored (3 of them, one was DIY, two were vendors) + pros and cons
Slide 4 - our solution and why they preferred it 

One of the best lessons I ever learned.

Meet Elsie ❤️

This 5 year old sweetheart LOVES every human and dog she meets. 

At 5 years old, she’s past all that puppy mischief, but still has plenty of joy and tail wags to share. 

She’s gentle, loving, and ready for a home with someone who will love her as much as she loves them. 

Not sure if you’re ready to adopt? Foster her! It’s completely free. 

Photo credit: Nicholas I. Knuth 📸 

Available at Many Paws Global Rescue in Palatine, IL.

(PS - if you’re looking for Saturday plans, I’ll be at Buffalo Creek Brewery in Long Grove, IL for a Many Paws adoption event today from noon-3. Come meet your future sidekick ❤️)

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The Battle

Matt Green

Jen Allen-Knuth

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Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Matt Green's LinkedIn Performance

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