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

Lindsey Fine Coaching

Drawing on almost 20 years of experience and a track record of delivering results at some of the most notable tech companies in the world, I help founders and sales teams cut through the noise and sell with clarity, confidence, and consistency. 

Here's how I can help:

Sales Coaching – Go from sporadic pipeline to consistent revenue
Storytelling & Messaging – Turn complex ideas into clear, compelling narratives that actually land
Call Coaching – Get real-time feedback on live or mock discovery/demos to sharpen delivery and boost confidence
Workshops & Speaking – Sessions that teach you how to sell without selling out
Advising – Fractional support for early GTM motion and strategic visibility

Available for 1:1 coaching, VC portfolio support, and live workshops.

GTM & Growth Partner 

hubble

Here's how I can help:
- Sales coaching 
- Storytelling & messaging for GTM/fundraising
- Discovery & demo call reviews

Book here: https://www.hubble.social/lindseyfine

Mentor

the old girls club

The old girls club is a virtual gathering space for talented women and non-binary people working in male-dominated industries. Members are committed to giving and receiving non-performative & tactical support in the form of intros, insights, examples, guidance and resources.

Member

Sales Assembly

Featured Thought Leader

Chief

Chief is the only organization specifically designed for the most powerful women executives to strengthen their leadership, magnify their influence, and pave the way to bring others with them. It's mission is to drive more women into positions of power and keep them there.

WorkTango Inc.

SVP of Sales

Dyspatch

Empower your team to create, innovate, and grow with the Dyspatch Email Builder. 

Dyspatch is an industry-leading solution for email production and management. With Dyspatch, you can build engaging, interactive emails, without having to write code. By leveraging a custom modular email design system, non-technical teams can deploy beautiful, on-brand campaigns faster and achieve greater operational efficiency.

VP of Sales

Amazon Business 

Head of Mid Market Sales - Food Service & Hospitality and Information Technology

Sales Leader, Amazon Business

Amazon Business is a new marketplace on Amazon.com that combines the selection, convenience and value customers have come to know and love from Amazon, with new features and unique benefits that address the needs of businesses.

Amazon Business provides a unique shopping experience with access to hundreds of millions of products, business-only selection, free two-day shipping, business pricing, multi-user business accounts, approval workflow and much more

Corporate Advisor, Amazon Business

iDonate

Despite an increase in wealth, the world's level of giving has been stuck at 2% for decades. Our mission is to transform charitable giving by changing the way the world thinks - and more importantly, acts - around giving. We develop software and services accessing billions more in potential gifts to support the organizations that are trying to make a difference.

Enterprise Account Executive

Dropbox

Dropbox Business gives IT the administrative tools they need. Manage users, monitor activity, and control sharing permissions, all from one central Admin Console.

Enterprise Accounts - Dropbox Business

Growth-Focused, Compassionate Leader | Amazon, Salesforce, Meta & Dropbox Alum | CHIEF Member | Mom²

I’ve been told “you’re not good enough” more times than I can count.

When I applied to early decision to Cornell, my Chemistry teacher laughed at me. She wasn't wrong for that - I got straight up rejected. But “no” on a piece of paper wasn’t going to cut it. I called the Dean of the school every single day until he finally took my call. He told me exactly why I didn’t get in, and what I needed to change. A year later, I walked through the doors as a student.

𝗧𝗵𝗮𝘁 𝗺𝗼𝗺𝗲𝗻𝘁 𝘀𝗵𝗮𝗽𝗲𝗱 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴. 𝗜𝘁 𝘁𝗮𝘂𝗴𝗵𝘁 𝗺𝗲 𝗵𝗼𝘄 𝘁𝗼 𝗮𝗱𝘃𝗼𝗰𝗮𝘁𝗲 𝗳𝗼𝗿 𝗺𝘆𝘀𝗲𝗹𝗳 — 𝗰𝗹𝗲𝗮𝗿𝗹𝘆, 𝗱𝗶𝗿𝗲𝗰𝘁𝗹𝘆, 𝗮𝗻𝗱 𝘄𝗶𝘁𝗵𝗼𝘂𝘁 𝗮𝗽𝗼𝗹𝗼𝗴𝘆.

Since then, I’ve built a career leading sales at some of the biggest names in tech. I’ve also been fired while six months pregnant and told to pretend it was my choice. I’ve lost a parent while fighting for a leadership role. I’ve been told I was “too emotional,” underestimated, rejected, and sidelined.

Each experience redirected me toward something I couldn’t see coming: a chance to grow differently, to lead differently, to prove resilience isn’t about never breaking — it’s about what you build after.

What drives me now isn’t the titles or logos — it’s developing people and creating clarity. That shows up in the enablement programs I design, the leaders I coach, and the brand partnerships I choose.

I work with:

- 𝗕𝗿𝗮𝗻𝗱𝘀 who want authentic partnerships rooted in real stories and human connection.
- 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 and revenue teams who need clear, confident messaging and enablement that sticks.
- 𝗔𝘂𝗱𝗶𝗲𝗻𝗰𝗲𝘀 who crave speakers willing to share the truth, not just the highlight reel.

My superpowers? Connection, clarity, and turning challenges into growth.

I believe in pushing back against hustle culture and building success on honesty, resilience, and compassion. If you’re a brand looking for an authentic partner, a company needing enablement that actually gets adopted, or a team that wants to sell with clarity — let’s talk.

Lindsey Fine

Grateful for all who've served - especially mine. 

This is my Dad. 
Many years before I ever understood what service really meant. 

His service shaped how I lead, how I parent, and how I show up. 

He taught me that it wasn't just about sacrifice. 
It's about quiet strength. 
Integrity. 
Doing the hard thing because it's right, not because it's easy. 

To every Veteran: thank you for setting the standard for the rest of us to strive to meet. 🇺🇸

Sales Leadership Coach & Fractional Revenue Partner | Coaching leaders. Guiding teams. Driving revenue. | Amazon, Salesforce, Meta, Dropbox Alum | Mom²

Today's high was 67. 

My kids lost it when I told them.  

IYKYK.

I tried to give something away for free.
No one wanted it.

Last week, I listed a perfectly good IKEA rug on my local “Buy Nothing” group.
No stains. No damage. 
Just no longer needed. 

Crickets.
One person commented, then vanished.
That was it.

So I deleted the post and relisted the exact same rug on Facebook Marketplace for $40.

Within minutes, my phone lit up.
Multiple offers.
Sold in an hour.  

Same rug. Same photos. Same platform.
Only one thing changed: the price.

We assume “free” makes something irresistible.

But often, it does the opposite.
“Free” can make people suspicious.
It can signal: cheap, broken, not worth my time.

A price, on the other hand, communicates value.
It says: This is worth something.
It creates fairness instead of charity - an exchange, not a giveaway.

In business - and life - pricing is rarely just about money.
It’s about meaning.
It’s how we tell the world what something is worth... and what we believe about ourselves.

We all do it. 
We downplay what we're good at. 
We overgive. 
We under charge. 
Then wonder why others don't see the value we do. 

But value isn’t just what you offer. It’s how you frame it.
When you treat your work as valuable, others usually follow.

Sometimes the best way to help something find its place isn’t to give it away.

It’s to price it right. 

What's something you used to undervalue ...until you priced it right? 

📸 of said rug
which happens to be designed by Zandra Rhodes (a renowned British fashion and textile designer)

I saw genius marketing this week. 

And it happened in a Target parking lot. 

Sunday night. I realize we're out of milk, snacks - basically everything. 
I put in an order for Target delivery and set my phone down.

I came back later to messages from my shopper. 
The last one is a picture of their car with a note saying they were on their way.

I recognize the car instantly.
A  bright red Tesla covered in super hero dog illustrations. 

Groceries arrive. 
I start unpacking ..and there's a card inside. 

"Our day job delivers therapy and Rosie's magic pups to kids in need. In lieu of a tip, consider a small gift" with a QR code. 

Done. 

Turns out, the founder of The RosiePups Project delivered my groceries. 
He turned a side hustle into a moving billboard for his mission. 

No ad budget. 
No agency. 
No funding. 

Just creativity and the willingness to use what he already had. 

We're always wanting more. 
More budget. 
More time.
More resources.

But  sometimes the smartest move is looking at what's right in front of us. 

What part of your everyday could become an opportunity?

Most 'underperformance' I've seen as a leader wasn't a skills problem.
It was a clarity problem - with a little fear hiding underneath. 

I learned the hard way. 

I assumed people knew what I meant. 
I assumed they'd speak up if they were stuck.
I assumed silence meant understanding. 

And you know where I'm going here.. when we assume..(I'll let you fill in the rest 🤣) 

Everything shifted the moment I started asking one simple question: 

"What's blocking you?" 

Not in a performance-review way.
Not in a "prove yourself" way. 
Just genuinely curious. 

Most people want to do well.
They just don't want to look lost. 

When clarity goes up, fear goes down.
And performance follows. 

Clarity + safety > more training and tools.

If you're leading through panic, you're not leading.

It's Monday morning. 

If you're a sales leader and you managed not to ping your reps over the weekend - congrats, you get to keep your "leader" title. 

If you didn't? 
Time to re-evaluate. 

Your team doesn't need a weekend pipeline panic from you.
They need to see what calm confidence looks like. 

Great leaders don't create urgency 24/7. 
They create safety so people can sustain it Monday through Friday. 

Share this with the leader who models calm under pressure.

Leaders don't crack from pressure. 

They crack when they lose perspective. 

The higher you climb, the easier it is to confuse urgency with importance. 

When everything feels loud, step back.
Zoom out. 
Get above the noise. 

Decisions get a lot easier when you're looking at the full picture, not just the two feet in front of you. 

Heavy week? 
Zoom out.
Perspective is a performance tool.

taplio

The Battle

Matt Green

Lindsey Fine

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The Battle

Matt Green

Lindsey Fine

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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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