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

Christina Brady

Luster

Helping GTM teams polish and shine through practice.

CEO & Co-Founder

Pavilion

Chicago Chapter Head

Women in Sales

Head of Community

Loanspark

Advisor

Marketers in Demand

Taking The Lead is our podcast that features conversations with the most Accomplished, Admired and Amazing Female B2B Revenue Leaders.  In each bi-weekly episode, we'll dive into a tactical topic to help our listeners (regardless of gender or seniority level) learn how to be better, faster, and smarter as they navigate the craziness of the Revenue world within B2B Tech. Plus, we'll have a little fun along the way, keeping it candid, real, and transparent. No topic is off the table, and authenticity is the goal.

For show info or to listen to recent episodes, https://marketersindemand.com/taking-the-lead/

Please listen, subscribe, and share!

Host of Taking The Lead Podcast

Spekit 🐙

SVP of Sales

Sales Assembly

Chief Strategy Officer

As our industry’s only Scale-as-a-Service platform, we’re the trusted partner for leading B2B Tech companies on their journey to Scale Better, Scale Faster, and Scale Smarter.

Our frictionless & all-inclusive membership platform provides our members with access to the programs, trainings, certifications, tools, talent, resources, strategy, advisory, and peer connections they need - all in one place

President

Glassdoor

-Presidents Club Award winner - FY20
-3rd line leadership/executive

Head of Sales, Growth

Sales Manager, Enterprise Growth

-Opened, hired, and helped grow the new Glassdoor Chicago office
-Managing a growth team of sales reps, aimed at maintaining and developing relationships
-Achieved 105% of FY17 annual target
-Presidents Club Award winner - FY17

Sales Manager, SMB Growth

Groupon

-Selected to lead a high value pilot team of hand picked reps, aimed at redefining Groupon’s future sales strategy and operation

-Participate in weekly meetings with the CEO to report progress and brainstorm

-Create and implement a new, vertical specific, sales process, value prop, and customer engagement strategy

-Short term success includes 50% increase in team contract productivity, and MOM GP growth

Head of Revenue, Groupon Things To Do

-Managed #1 revenue producing team in Local, over 7M/Quarter, attended presidents club in 2015 for 2014 achievement

-Responsible for developing, training, mentoring, coaching and supervising sales reps on selling skills including, but not limited to: customer site sales calls and lead conversion skills

-Prioritized and allocated resources to ensure adequate support for sales reps

-Monitored and aligned rep activities, including sales volume, deal quality, and pipeline

-Trained sales reps on deal structure and strategy that are proven models for successful achievement of merchant’s desired outcomes

-Ensured sales rep understanding of the cities location, dynamics, consumer demographics, merchant visibility, and accessibility

Divisional Sales Manager

-Delivered on the end-to-end new business development process, including email campaigns, setting/coordinating customer calls, meetings, delivery and creation of follow-up materials, and maintained ongoing contact to grow relationships

-Received Award for Sales excellence in 2012, top 20% of reps

-Consistently exceeded performance metrics and promoted to top 15 market (based on gross revenue) within 9 months

Account Executive

MetLife

-Worked with minimal management selling Metlife products to Group clients. 
-Maintained and grew book of business through aggressive product sales, upsells, and renewals within assigned territory.
-Received Super Starter Award for Sales that exceeded expectation.  Promoted within the first year to a team lead.

Licensed Financial Associate/Account Executive

GTM Builder | Host of Taking The Lead | 2x Demandbase top 100 Revenue Leader | People Leader | SKO Speaker | Animal Enthusiast

With 18+ years of overall SaaS sales experience, covering both land and expand strategies and teams, and 11+ years of executive leadership in the SaaS space, Christina has a proven track record of leading individuals and organizations to growth & profitability through creative, scalable, and targeted strategy. As a former artist, musician, and improv performer, she has a genuine passion for building culture, coaching & developing leaders, and producing top-performing Sales and CS teams across small to enterprise organizations. Christina uses her experience, data driven approach, and people first mentality to revolutionize how revenue teams practice and ingrain learning, skills, and ongoing development. On a daily basis, she is energized by the opportunity to help companies of all sizes grow and make a worldly impact.

taplio

The Battle

Matt Green

Christina Brady

Followers

Posts

Engagements

Likes

Performance ScoreMatt Green's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Matt Green

Christina Brady

Followers

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

Ready to grow your LinkedIn presence?

Performance ScoreMatt Green's LinkedIn Performance