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

Neil W.

CEOs call me when ok is not good enough - Fractional CRO @revenue•x | Founder @PORCH

Revenue is everything - and nothing else matters.
It's true - revenue solves all problems.  

But to get it - in todays market - it's all about execution. 
GTM execution is the only moat anymore. 

And if you don't know how or don't have a team that gets sh!t done and moves fast, you are in a heap of trouble. 

You don’t need more ideas. You need people who can lead and execute and get sh!t done.

That's my superpower - Creating, building and executing GTM plans that generate pipeline and revenue. 

I focus on early-stage and medium-sized businesses to BUILD and EXECUTE GTM experiments to accelerate sales. I work in partnership with CEOs to build the foundational elements, processes and skills required for a successful GTM.

To learn more about weitzmanGTM, check out www.weitzmangGTM.com or DM me.

--

I am also the Founder of PORCH - an exclusive club for international and immigrant entrepreneurs for the personal side of the journey (the stuff that accelerators don’t do). To learn more about the PORCH, check out www.porchcommunity.com.

--

I try my best to...
- Punch up and go high when others go low 
- Admit mistakes
- Follow logic and reason
- Stick to the POP principles (Passionate, Optimistic, Perseverance).
- Keep my 100% Say/Do ratio

Co-Founder and Executive Coach

Your blueprint for starting and growing your fractional or consulting business.

Everyone loves the “young founders”.
Build a startup at 22.
Get on the Forbes 30 under 30.
Raise $5M before you can legally rent a car.

But here's the truth nobody wants to talk about:
The average age of a successful startup founder is 45.
(Before you ask me - Source: Harvard Business review)

Not 25. Not fresh out of school. 45!
And that makes complete sense:
You've seen what works (and what's complete garbage). 

You've built relationships that actually matter. You know your strengths and stopped pretending to be someone you're not. You've failed enough to know how to recover.

Ray Kroc was 52 when he started McDonald's. 
Vera Wang launched her fashion line at 40. 
Sam Walton opened the first Walmart at 44. 
Colonel Sanders franchised KFC at 62.

I spent 17 years at Nielsen before starting weitzmanGTM at 43. I was 48 when i started PORCH with Hunter after learning what accelerators fail at. And I have a new company we are launching soon (stay tuned!). 

These are not large unicorns (to say the least) but for me it took the right alignment of risk, courage, innovation and ambition to make it happen. 

I'm still figuring sh!t out. Still experimenting. Still failing and learning.

There's no magic age where you're "supposed to have it all figured out."
And there's definitely no such thing as "too late."

Want to start something? Start it. Want to pivot? Pivot. Want to try that idea you've been sitting on? Try it.

Your experience isn't baggage.
It's your unfair advantage.

🤙Neil Weitzman

Getting sh!t done to grow (when “ok” is not good enough) | GTM Advisor - Fractional CRO / Operator | Founder of PORCH

Sales might be the worst career for 90% of people today.

Sounds harsh, but let’s be real. Most people get into sales for the hype, not the heat.

They see the commissions, the fancy titles, the “six-figure OTEs” on LinkedIn.…

but not the stress, the constant rejection, or the daily reinvention this job demands.

If you can’t:

→ Communicate clearly under pressure
→ Learn fast when everything changes
→ Adapt your playbook constantly based on the market and human behavior
→ Build trust with people who don’t need you yet

Then sales will eat you alive.

Because this game isn’t about charm anymore.
And, it’s not just about a steak dinner and tickets to the game. 
It’s about business acumen.

You’ve got to understand finance, negotiation, psychology, tech, data, and yourself.

The truth?

The top 10% of sellers aren’t the loudest. 
They’re the sharpest.
They change constantly. 
They learn constantly. 
They move faster and respond sooner. 

If you want easy money, go somewhere else.

The market’s evolving and buyers are smarter than ever before.
And the only ones still closing are the ones who’ve evolved with them.

So before you jump into sales for the paycheck, ask yourself:

“Do I actually want to work for it?”

Hot take: Torturing your sales team until they hit bigger numbers isn't actually a GTM strategy.

Raising quotas doesn’t increase revenue.
In fact… it usually kills it.

I’ve been saying this for years:
Revenue is everything. Nothing else matters.
But the way you get that revenue?
That matters a hell of a lot.

And here’s what I’ve learned (the hard way):
The tighter you squeeze a sales team, the worse they perform.

Companies love the “raise the quota → raise the revenue” fantasy.
I’ve never once seen it actually work.

Here’s what does work;
Lower the quota.
Make the goalpost predictable.
Give your reps room to breathe.

Because when reps feel safe, confident, and “in control,” their performance skyrockets.

When they feel like they’re constantly failing?
Everything tanks -  morale, momentum, pipeline, and yes… revenue.

I’ve tested it multiple times across different teams:
Cut quotas by ~20% → Revenue per rep increases.

Not because reps suddenly get better …but because pressure shifts from survival mode to winning mode. And winning compounds.

Look, I know t’s not magic.

You need leadership, coaching, standards, and a real GTM plan behind it.
But let’s stop pretending quota inflation is a strategy.

It’s not. It’s a CFO shortcut disguised as motivation.

If you actually want more revenue?
Build confidence, consistency and momentum.
That’s the real hack.

What’s your experience?
Do higher quotas help or hurt? 👇🏽

112,732 people have been laid off in 2025. In 2026 Asad Zaman predicts 500K - 1M cuts in US tech. HOLY F!


Thats a lot of people who want to work and will have a hard time finding jobs. 
There is a lot of them out there right now. 

Some of them are reading this or you know someone looking for a job.

Let's f'in help them. 

Because being worried about feeding your family is the worst feeling in the world. I have been there and if you haven't. count yourself blessed.

Let's help someone find a job today.

PLEASE Tag someone, repost, comment or do something to help someone find a job 💚

--

EXEC / LEADERSHIP ROLES:

SVP Sales Kasada (PST timezone only)/ Nick Rieniets 
https://lnkd.in/ervQJn2B

VP Marketing Momentus Technologies / Nicole Smith 
https://lnkd.in/ehYkMhzp

VP of CS Channelscaler  / Jason Moore 
https://lnkd.in/eJhea2Tb?

VP Product at Tilt Brandon Salisbury 
https://lnkd.in/eEKtwhVv

Head of Marketing at N.Rich / Markus Ståhlberg 
https://lnkd.in/eHyngj_u

SVP Sales (PST time zone only) at Kasada / Nick Rieniets 
https://lnkd.in/ervQJn2B

Head of Sales / VP Revenue - Breakout AI Marketing org / Kelsey Robinson Christopher Gannon 
https://lnkd.in/e7Cje9Vh?



MANAGEMENT / IC ROLES:

Sales Manager at Macrobond / Jason Brausewetter 
https://lnkd.in/exjjRP_v

AE at Space Dinosaurs / Joseph Krasko 
https://lnkd.in/e3F8X25s

Sales Enablement & Operations Manager at Greenlight / Matt Wolf 
https://lnkd.in/e6e2rdSU

Sales Operations Analyst/Manager at Keynes Digital / James C. 
https://lnkd.in/egwj4JnS

5 more SALES roles here from Sales Talent Agency / Asad Zaman 
https://lnkd.in/eDbEWqzM

➕ 147 more open jobs from GTMfund portcos (I am a proud LP) https://lnkd.in/eDVVMeDA


Check Asad's prediction here: https://lnkd.in/eiK2qwQp?

P.S For more, ring the bell on LinkedIn and follow me at GTM of GTFO https://lnkd.in/eN7BWyJb

How come we don’t have a closed lost reason code that says “I fucked up” ?

Our closed lost deal data is shit because we likely dont even realize it was our fault and if we do, we wont often own our mistakes in the data like that.

Unfortunately sales reps are often the reason we lost.

That not an insult it’s just the truth.

We didn’t 
- do great discovery
- we talked more than we listened
- we never crated urgency
- didn’t help the champion create an effective business case for the CFO
- didn’t multi-thread properly and never understood that Sally loved the competitor and was influential to others


All of these things are fixable
The first step is admitting I’m right
The second step is ensuing the process is right
The third step is coaching on it. 


Matt Green just wrote a good post last week that touches on this - go read it.

The quickest way to expose a broken revenue org is to watch how they hire. I see it all the time as a fCRO. 


I am handed a paradox. Asked to rebuild a revenue engine but do not own the full calendar. Yet, my mandate is often to hire people who will outlast me.

I have lived this from every angle. Years inside corporate as the interviewee who did seven rounds for a role. 

Countless hours as the interviewer trying to separate charm from competence. 
Now as a fractional CRO who has to pick builders fast and leave behind a team that wins without me.

Here's how I approach hiring when clock, culture, and calendar are not all mine.

1) Story first. Scope second. Process third.
Strong people select strong stories. Before reqs or scorecards. Write six simple lines.

Why we exist
Who we serve
The problem we solve
What winning looks like
What you will own 
How we behave when things get hard

This becomes the spine for everything 


2) Speak like a human and activate warm networks
Jargon repels the people you want on your team. Rewrite everything in plain English. Ask the CEO to record a 2min video explaining the mission and telling the company story. 

People are attracted to candor and simplicity. 


3) Use video to filter for energy, clarity, and curiosity

CV's list dates and jobs but anyone can write anything - especially now. 
Video shows us the human. I ask every candidate to record a video answering a few prompts

Tell me your story
Why does the problem we solve excite you
Why are you a fit
What is one question you would ask our customers 

If they won’t do the video. Disqualified. 

Score each on energy, clarity, and curiosity from one to five. 


4) Interview on data, not vibes
I've seen the loudest voice in the room push through a hire because “she had great energy.” The deal board paid for that mistake.

Use data-driven hiring - assign two competencies to each interviewer with fixed questions and a simple one to five score. Average the scores, set a bar, and only hire when the numbers clear it.

Use the Google and Amazon hiring method. Do NOT hire if anyone on the interview team disagrees. 

𝘕𝘦𝘦𝘥 𝘢 𝘵𝘦𝘮𝘱𝘭𝘢𝘵𝘦 𝘧𝘰𝘳 𝘢 𝘥𝘢𝘵𝘢-𝘥𝘳𝘪𝘷𝘦𝘯 𝘩𝘪𝘳𝘪𝘯𝘨 𝘴𝘤𝘰𝘳𝘦𝘤𝘢𝘳𝘥? 𝘔𝘦𝘴𝘴𝘢𝘨𝘦 𝘮𝘦. 


5) Tell the messy bits before they sign
Share everything. Transparency ⬆️ trust and ⬆️ retention. 
Share runway, quota math, win rate, tech stack, and the top risks you see. 
A-players get excited when they see the full field and tourists opt out. 
If you don’t want to be honest ask yourself why.


6) Treat candidate experience like brand experience
Do not ever ghost someone. This is their life, respect it. 
You were in this position once. 


Fractional leaders are not paid to be busy. 
We are paid to raise the bar and leave things better than when we got there. 



Full post here Pavilion's Independent Operator
https://lnkd.in/eGAdWqBc

Follow me @GTM or GTFO: https://lnkd.in/eN7BWyJb

weitzmanGTM – The Fractional Hiring Mandate

If you're in sales, you need to hear this.

Because most reps think their quota was set through deep analysis, AI models, market intelligence, and months of strategy work.

Nope.

Let me tell you how it actually happens in the majority of cases (especially with early-stage companies) because I’ve been in those rooms for 20+ years.

It usually sounds something like this:

CEO: “We did $3M last year… so let’s aim for $9–10M next year.”

CFO: “Love it. Looks great on the board deck.”

Board: “Perfect. Growth story locked.”

CRO: “ummmm… ok this is cool, but how are we doing this?”

And then the fun begins.

Nobody’s talking about:
→ CAC
→ Win rates
→ Sales cycles
→ Pipeline quality
→ Territory coverage
→ Product readiness

Nope, they’re reverse-engineering a number and hoping the math magically works.

Then someone says:

“Can we just… increase quotas and add a few reps?”
“Wait  let’s just get them to work harder!”

And boom - YOUR number is born.

Not from data but from hope. 

Here’s the part nobody tells you:

A delicious cake starts with the ingredients. 
A great year of hitting quota starts with the ingredients. 
They start with truth.

✔ What does our current engine actually produce?
✔ What levers do we realistically control?
✔ What talent do we have, and what talent do we need?
✔ What risks exist in the system today?

That’s where real revenue planning comes from.

After decades in GTM, here’s my rule:

If the target isn’t tied to data, capacity, and repeatable motion, it’s just a wish.

And wishes don’t pay bonuses.

AI isn’t the threat. Isolation is. 
AI is exposing the leaders that were never really leading in the first place. 

I watched a Simon Sinek clip this morning, and it hit me harder than I expected.

Here’s the part that stuck with me 👇🏽

We keep talking about AI, efficiency, automation, scaling GTM…
But the real advantage inside any company is still the same thing it’s been for decades:

Human connection.
Trust.
Risk management.
Attitude.
Work ethic.
And Strong Motivational Leadership. 

Sinek made a brilliant point:
Most of what we call “leadership problems” today aren’t caused by AI or Gen Z or hybrid work.

They’re caused by the same old issue:
People don’t feel seen, supported, or safe enough to ask for help.

I see this often. 

Teams aren’t failing because the work is hard.
• They don’t feel protected when things go sideways
• They’re scared to admit what they don’t know
• They feel disconnected… even inside the same Slack channel that you thought would solve everything about remote work. AI isn’t the threat. Isolation is.  
• They’re aren’t practicing and getting real-time coaching 


Strong leaders set the tone and lead by example.
• They defend their team and have their back
• They admit their own mistakes quickly and openly and they ask for help
• They bring the team together often (even when remote) - through SKOs, events, regular meetings, fun for the sake of fun, training and learning together.
• They implement a culture of practice and coaching - maybe the most important element to long-term team success IMO (BIG fan of Avarra for this -  check out my “Expectation Setting coaching use case here: https://lnkd.in/eQRpe3_2)


I believe that your GTM process breaks when trust breaks.
It accelerates when trust compounds.

AI can automate workflows, analyze pipelines, tighten ops and help in many areas. 
But it can’t replace clarity, empathy, or a leader people want to follow into the next quarter.

So ask yourself, 

Does your team trust you? 
Are you leading by example? 

Are you setting a culture of practice, of real-time coaching, defending them when needed, admitting your own mistakes, asking for help, leading with optimism, etc.?

Because how you answer that question will define your next 12 months more than any new shiny object you bring in.

the Canadian tech scene lies to itself  
Tobias Lütke from Shopify tweeted "Alex absolutely nails it here with every part of this"

The Canadian tech / start-up world lies to itself - basically saying..
• SRED sucks
• MaRS sucks
• Advice to founders is a net negative value
• Don't need more mentors/introductions


IMO the major reason is because most accelerators/incubators rely significantly on government funding and as such worry more about getting the funding, keeping their jobs, and hitting useless metrics than doing what actually matters and moving the needle for founders.

According to ChatGPT

Government funding to accelerators 
Canada = High / USA = Low   

Reliance on public money 
Canada = Very high / USA = Minimal   

Private VC involvement 
Canada = Moderate / USA = Very high   

University programs 
Canada = Publicly funded / USA = Endowment or corporate funded   

Corporate accelerators 
Canada = Some / USA = Tons   

Likelihood a random accelerator receives gov money 
Canada = High / USA = Low  

Canada: Most programs rely on public funding to operate.
United States: Government supports founders, not the accelerators themselves.


Listen to the whole thing Other Stuff Podcast with Alex Danco from Andreessen Horowitz - it's good stuff. 
https://lnkd.in/eTHrpEuR


What do you think?

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