Leslie Greenwood

Chief Evangelist, Community Strategist, Co-Founder of Wednesday Women, Startup Advisor, Ex-Stay-At-Home Mom

I'm the Co-Founder of Wednesday Women and the Founder of Chief Evangelist Consulting: two ventures grounded in a core belief: community isn’t a tactic, it’s a force.

Wednesday Women began as a ripple in 2023 as a small, intentional effort to elevate executive women. We amplify women’s voices on LinkedIn, on stages, on podcasts, not as polished personas, but as their real, remarkable selves (the woman behind the title). Our public platform is for everyone, and we’ve built a private membership for executive women who want to go deeper with that mission and create connections both help unlock challenges but also are their biggest cheerleaders. 

Through Chief Evangelist Consulting, I help companies design community strategies that create lasting engagement. With 20+ years in customer-facing leadership roles, I approach community as a strategic lever, rooted in trust, value, and connection.

At the heart of everything I do is a belief in the power of evangelism, authenticity, and shared momentum.

And yes — I run on coffee, dark chocolate, trying (and failing) to keep me very vocal dog in check and talking loudly about diversity in tech.

Ambassador

Advocating for Pavilion’s mission of helping every leader and their team achieve their professional potential through community-powered learning. I will be supporting key initiatives, developing and teaching curriculum for Pavilion University and providing over 10,000 members with leadership advice. Join us at joinpavilion.com.

I’ve been seeing a trend….
more women walking away from corporate life to go fractional, consult, or build their own thing.

And I get it.
I did too.

At some point, I realized I’m “consciously unemployable”. 

That’s a choice. 

Not because I can’t play the corporate game (well actually if you know me, I can’t 🤣), but because I finally saw how much of it was built on rules that were never written for us. And I was done building others’ dreams.  

As Sarah Allen-Short wrote,  

“Liberal feminism didn’t ruin the workplace. It exposed it.”
(If you read the NYT article, you’ll get the reference.)

What we’re watching isn’t women giving up. It’s women waking up.

“Lean In” taught women to play the old game. This era’s about building a new one.

When you realize the system was never designed for you, you start creating something better.

(📸: Quote from Sarah’s Substack Work Doula — worth the read.)

 #futureofwork #womeninbusiness #founderlife #fractionalleadership

Leslie Greenwood 

💜 Shining the Spotlight on Exec Women, Co-Founder of Wednesday Women, Community Strategist, Chief Evangelist, Startup Advisor, Ex-Stay-At-Home Mom

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Andrea 🤓 Lechner-Becker and Raja Walia arguing just made my morning!  

That’s all, that’s the post. 💜 

And yes, Erin Kasmarick is still the HubSpot wizard 🧙‍♀️! We 💜💜💜💜her.

AI can’t invent weird. It can’t really do different. This is still where humans have the competitive advantage 

Think about Apple’s “1984” ad.
Or, Coinbase’s random bouncing QR code.

No robot’s out here dreaming those up. 

Those ideas hit because they were so human. Unexpected. Odd.
The kind of weird that makes you stop scrolling and go, “Wait, what?”

That’s what AI can’t fake.

It can totally take your ideas and scale them. But if what you feed it is already kinda basic… it’s just going to spit out more basic.

What’s that mean for us humans? Creativity actually matters more now. Because AI’s like this giant volume knob. Whatever you give it, it just cranks it up.

Bottom line: The magic happens when a human is brave enough to think weird.

We unpack this (and a few more “AI vs. human creativity” hot takes) in the full episode.
Catch it here → https://lnkd.in/gCvusPW6

#MarTech #Marketing #GTM #RevOps #AI

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

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The Battle

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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);}Leslie Greenwood's LinkedIn Performance

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