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

Todd Caponi

Sales Melon

A consumer behavior research study changed my life. While that may sound odd, it fueled my fire to take a wide range of behavioral science, research and data, and use those elements to drive simple solutions into the sales and sales/revenue leadership world. I now speak and teach revenue organizations and their leaders on leveraging transparency and decision science to maximize their revenue capacity.

Founder, Speaker (CSP®) & Workshop Leader

The Sales History Podcast

Bringing the incredible (and sometimes strange) brains from the profession of sales' past to the 2020s.

Sales History Nerd & Host

Matt Holt Books

A simple framework applicable in every common business-to-business sales scenario for building trust and leaving negotiating anxiety behind. (LAUNCHES JANUARY 27TH, 2026 - PRE-ORDER NOW)

Author, Four Levers Negotiating™

Ideapress Publishing

Author, The Transparency Sale & The Transparent Sales Leader

GlassHouse.biz

Board Advisor

Sales Assembly

Advisory Board Member

National Speakers Association

Certified Speaking Professional (CSP®)

ShoppingGives

VentureSCALE

Managing Director

Entrepreneur In Residence

PowerReviews

During my tenure as SVP of Sales & Chief Revenue Officer, PowerReviews became the fastest growing tech company in all of Illinois (according to Deloitte - period of 2014-2017)

Chief Revenue Officer

As it turns out, being transparent sells better, retains better, grows better & leads better. I speak (CSP®) and teach revenue organizations how we as human beings engage, prioritize, and decide - then how to use that knowledge (for good...not evil!) in their 𝐦𝐞𝐬𝐬𝐚𝐠𝐢𝐧𝐠 (informal and formal), 𝐧𝐞𝐠𝐨𝐭𝐢𝐚𝐭𝐢𝐧𝐠 and 𝐫𝐞𝐯𝐞𝐧𝐮𝐞 𝐥𝐞𝐚𝐝𝐞𝐫𝐬𝐡𝐢𝐩. 

I wrote two award-winning books about it, 𝘛𝘩𝘦 𝘛𝘳𝘢𝘯𝘴𝘱𝘢𝘳𝘦𝘯𝘤𝘺 𝘚𝘢𝘭𝘦 and 𝘛𝘩𝘦 𝘛𝘳𝘢𝘯𝘴𝘱𝘢𝘳𝘦𝘯𝘵 𝘚𝘢𝘭𝘦𝘴 𝘓𝘦𝘢𝘥𝘦𝘳. I have a third book coming out in January of 2026 called 𝘍𝘰𝘶𝘳 𝘓𝘦𝘷𝘦𝘳𝘴 𝘕𝘦𝘨𝘰𝘵𝘪𝘢𝘵𝘪𝘯𝘨.

I am a multi-time C-Level sales leader, a behavioral science and sales history nerd, and have led in seven different roles - including at two companies through successful exits. One of them had a double exit (IPO, followed by an exit valued at ~$3B) 

I achieved the exclusive status of CSP® (certified speaking professional) in 2024, which only ~500 active speakers have achieved in the world.

Founder, Speaker & Workshop Leader

A consumer behavior research study changed my life. While that may sound odd, it fueled my fire to take a wide range of behavioral science, research and data, and use those elements to drive simple solutions into the sales and sales leadership world.

It’s the first week of November. The leaves are falling. And so are the fake expiring discounts!

B2B selling organizations everywhere are already telling prospects, “This offer expires November 30th!” or “Prices go up after December 18th!”

👉 Ya know…those “expiring discounts” don’t accelerate deals. They slow them down. Right?

Think about your own buying habits.

If there’s clothing or electronics you’ve been eyeing, and you know Black Friday is coming, do you buy now?

Of course not. You wait—because you’ve been taught that prices will drop right after Thanksgiving.

Now step into your buyer’s shoes. What have we taught them?

Your “end-of-month” or “holiday” discount sends the same signal:

“If I didn’t do anything to get this discount, there’s probably more coming if I wait.” Or at the very least, they know when to ask for the moon.

So they wait.

Be honest...when December 18th comes and goes, will your discount really disappear if they sign on December 26th?

Probably not. But ok…I’ll go along. If said discount actually does go away, haven’t you just trained them to wait again next time you offer it? End of January? End of Q1? 

The better path? Mutual alignment.

“There’s tremendous value in our ability to predict our business. There’s value in our ability to forecast accurately; we make better investments, allocate resources effectively, and keep investors happy. If you can help us improve that predictability, that’s something we’re willing to pay for in the form of (requested concession).”

I know, that’s a generic sentence, and there’s more to it. But take a breath before throwing your coupons around this Fall. 

I go much deeper on this in my upcoming book, Four Levers Negotiating, releasing January 27, 2026 (available for pre-order now).

p.s. This is just one of The 7 Deadly Sales Negotiation Sins I shared with Armand and Nick on their most recent episode of the 30 Minutes to President's Club podcast. Get it wherever you listen!

Transparency Nerd | Sales Historian | Keynote Speaker (CSP®) | Sales & Leadership Trainer | 3x Author

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