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 couldn’t find any women experts. 
I don’t know any women speakers. 
I didn’t realize I built an entire exceptionally homogeneous event. 🤯

Seems to be a good day to remind everyone that if you’re looking for expert speakers for your event, I have an easy resource. 

Go to a certain website that might be where I work.  

Hit “Get Involved”

Hit “Find Speakers” 

Search a list of over 300 executive women. Ungated, free, keyword searchable.  

Reach out to them and say you found them thru Wednesday Women.  

Kinda easy actually. 


#noexcuses #nomoremanels #executivewomen #keynotespeakers

Leslie Greenwood 

💜 Bringing public awareness and private support to executive women, Co-Founder of Wednesday Women, Community Strategist, Chief Evangelist, Startup Advisor, Ex-Stay-At-Home Mom

🗓️I’m posting this on March 1 on purpose.

Because honoring Black women should never be confined to the shortest month of the year.

And as the mother of two amazingBlack women, this is personal for me.

Black History Month may end on the calendar, but the brilliance, leadership, influence, and impact of Black women do not.

So rather than letting the moment pass with February, I want to carry it forward.

I’m grateful for the Black women whose voices shape conversations, challenge assumptions, build companies, lead teams, create culture, and move all of us forward.

Not just in history.

The work is to keep noticing, keep crediting, keep amplifying, and keep showing up long after February ends.

March 1 felt like the right day to say that out loud. 💜

#BlackHistoryMonth #BlackWomenInLeadership #WednesdayWomen

29 new friends 
15 Wednesday Women members 
2 board members 
4 states 
A flight delayed until 4am 
Tears and cheers for a long awaited job offer. 
A gator 
Service beyond expectation 
Not only beautiful wines but the science and history behind them 
Local women artisan vendors - the honey chocolate 🤯
A celebrity chef - yes I got a selfie!! 
Gifts galore 

The biggest gift? 🎁 

Seeing these women take time away from demanding jobs, new babies, intense job searches and their families just for themselves.  

A little restoration, weaving the spider webs of connection, and possibly that well needed nap on the way back to the city.  

As one member said more than once, “I’m proud I’m putting myself first.”  I couldn’t have said it better myself.

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So you show up at the coffee shop you made a reservation for your event 15 minutes early as requested and no one is there. 

🚫 It’s closed. 
Lights are off. 
20 women are mingling outside.
Probably an event planner’s nightmare.

But they don’t have “Super Sam”! Samantha Archuleta found us an alternative location within five minutes that would be setting up our table on our walk over. Amazing! 

Sometimes things are just meant to happen. Our coffee was delicious, we got in a few hundred extra steps, we still had an amazing time learning about each other and finding ways we could support one another. 

And the extra bonus? Avotoasty is a woman owned business. Thank you to Sofia Guglani and your amazing team for working on the fly and helping us have an amazing event. We will absolutely be back. 

Robyn, Gwyneth Borden, Michelle Ji-Yeun Kim, Annette Sung, Holly Hon, Paula Mantle, Christina Mitine, Christina Singh, Aimie Vargas. Barbara Leavitt, Frankie, Michelle King, Gurlene Kaur, Arvita Tripati, MBA, Nellie Wartoft, Jieun Lee, ⚡️ Lori Dunn , Heidi Dickert, Mabel Liang

❓Who are the women in enablement I should know?

I’m looking for women who deserve more spotlight for the work they’re doing to help teams perform, influence strategy, and drive real revenue impact.

In my opinion, a lot of women in enablement are doing work that goes far beyond what the title suggests. They’re building the systems and momentum behind high-performing revenue teams. 

Honestly, many of them look a whole lot more like “revenue activators” than the traditional label gives them credit for.

And yet, some of the most strategic people driving revenue are still not getting enough visibility. 🤨

Let’s change that. 💜

Tag them in the comments or send in a nomination.

#womeninenablement #wednesdaywomen #revenueactivators

Now, how did Starbucks know that I was going on a work trip this week? #ubecoldfoam for the win.  

Wednesday Women nails representing.  

Bye Dallas, hello San Francisco and Napa! 💜

Let the travel hacks commence.  

1) Buy Wednesday Women purple suitcase because you saw it in the Morning Brew newsletter (brand partnership? 🤙😁💜).

2) Order your coffee as you’re driving into the airport or as you’re deplaning.  No long  line to then wait forever for your coffee.  Girls gotta have caffeine first thing.  

3) At least in Dallas, you no longer have to go to the airport to get TSAPreCheck. I got mine at Staples. #gamechanger 

4) When you’re traveling, do “community “everywhere”. Meaning reach out to your community and set up coffee dates.  I’m in SF and have coffee and dinner already planned for tonight.  Also 2 coffees and drinks set up in Seattle at the end of the month.  These are outside of our official events.  

5) Bring a good book. I’m always thinking about the experience and psychology of our events and reading Unreasonable Hospitality is taking this to a whole new level. 

Teach me! What other tips should I be using?  #travelhacks #sanfrancisco #wednesdaywomen

International Women’s Day sharing a date with Daylight Saving Time feels almost poetic.

A day about women.
A day with more light.

There are so many brave women I know who aren’t afraid to step into the light and just as many who aren’t afraid to /gently push/nudge/or shove, if necessary, another woman toward it.

Not every brave woman is the one at the center.

Sometimes she’s the one…
…making the intro.
…giving the endorsement.
…opening the door.
…sharing the opportunity.
…passing the mic.
… giving another woman that nudge to be seen.

That matters.

I’m grateful for the women I know who own their brilliance.

And I’m equally grateful for the women who see brilliance in someone else and refuse to let it stay hidden.

That kind of generosity can change careers, confidence, communities…all of it.

Take your turn shining in the spotlight or shine it on someone else. 

We need both. 💜

#InternationalWomensDay #WomenSupportingWomen #WomenInLeadership #WednesdayWomen

What did you do this week at work? I learned how to pitch better. You may be thinking, I don't sell anything. I don't need to know how to pitch. Well, I wholeheartedly disagree. 

I was lucky enough to host a Wednesday Women Members-Only Session with the iconic Precious L. Williams RainmakingSpeaker who talked with us about Positioning with Precision.  As you can tell, we were soooo bored and no one had any fun while learning sooooo much. 😉 

Here are a few bits of wisdom I took away from the call. 
Packaging is how you show up. 
Positioning is how the market perceives your value. 
Pitching is how you communicate that value to close. 

Everyone needs to know how to pitch well.

✅Job hunting - Pitching! 
✅Getting a raise or promotion - Definitely pitching. 
✅Talking to investors - They don't call it a "pitch deck" for no reason. 
✅Getting paid your worth to speak - Yep, still pitching. 
✅Sharing your business with a prospect - Well, duh! 
✅Getting your toddler to get dressed - You guessed it.
✅Asking your significant other to take out the trash - 😁 

So let's just say, we left with a lot of wisdom and fired up to implement it. 

But don't take it from me, I'm obviously biased. 

"Absolutely amazing session. I loved the energy and the information shared was on point. Thanks." 

"This was such a great lesson packed session - very practical, with tips I can and will implement immediately. Thank you Precious and WW."

Elizabeth McCalley.eth 🦋

CEO @StartStak | Strategy & GTM | Advisor | TED Speaker | Pavilion Executive + Chief Member I AI Artist & Practitioner

Hello! I’m Elizabeth McCalley 🦋, CEO of StartStak, an AI-Native company focused on early stage companies. With a passion for enterprise software, emerging tech, and services, I have dedicated my career to driving revenue for organizations. 

My approach is grounded in making non-obvious connections and staying steps ahead of market trends. I synthesize complexity and provide a clear, big-picture perspective to guide organizations into the future. I thrive on the challenges and opportunities that emerging tech solutions present.

StartStak is pioneering how companies utilize AI to get to market with precision. We are in the business of enabling the art and science of revenue and to help companies to stop pivoting.

🔹 StartStak specializes in: 🔹
- Market Strategy & Insights 
- Product Marketing
- Content Marketing
- Digital Marketing 

🔹 Principal Executive Skills🔹
- Enterprise Software and Services Sales Leadership
- Market Strategy & Business Development
- Alliance Management
- Executive-Level Presentations
- CXO Relationships & Negotiation
- Team Building
- Strategic Planning
- Market Research & Analysis
- Product & Portfolio (Re)Positioning
- Understanding of Emerging and Startup Technology Markets
- Analyst Engagement
- Web3 Fluent & Crypto Native

#StartStak #AINative #analytics #AI #StartUps #entrepreneurs #Strategy #Innovation #SaaS #Growth

elizabeth.mccalley@startstak.ai

Executive Member

Stealth Founders…..the ones still working in corporate, we love them. 🥷🏻

For the last few months, three founders have been finishing their corporate chapters. While they were doing that, StartStak.ai was building out their company. Really.

We are becoming a black ops go-to-market team. I have stealth founders in pipeline, who all still work in corporate. What they fear, is wasted time and money.

That's a healthy fear. 

Most startups launch and then try to figure it out. They piece together branding, hire outbound help, marketing freelancers, experiment with tools, rewrite their messaging three times, buy clay tables, pivot twice, and call it “iteration”…”lean startup”. 🙄

That isn’t iteration. It’s fragmentation and it’s expensive when you have one shot. The entire objective of navigating the “messy middle” of product market fit, is to get through it as fast as possible. That’s it.

There is one company designed for exactly that. #StartStak.

We don’t launch fragmented companies. We engineer cohesiveness BEFORE day one.
→ Brand architecture, the voice, the visual system
→ The markets they operate in and how the GTM is segmented by priority
→ Product narrative, messaging, strategic positioning, competition
→ The ideal customer, discrete personas, why they buy and why they “do nothing” 
→ Economic logic, acquisition motion, the data, system and processes

All aligned before the first announcement, because product-market fit isn’t luck. It’s architecture.

We are engineering coherence into new company business plans and that gets operationalized in the entire go-to-market. And, we are getting faster at this.

What we have come to understand is the reason StartStak companies have pipeline the day they launch is because we are experts in systems, data, process and execute with precision.

No, we are not a marketing company. We are a Product Market Fit company.

This week, we have a new company going live and it won’t look like a startup trying to find itself. This company will look deliberate. Calibrated and established. 

That’s the difference between “just launching” and “product market fit engineering”.

We don’t play startup. We design outcomes.

Why does this matter? Because time is money. 

#Launch #Startup #BreakingRules
https://lnkd.in/gw9JmA26

Founder & CEO @StartStak.ai | Strategy & GTM | TED Speaker | AI Practitioner & Artist | Chief Member

It took me one hour to fire a vendor yesterday and switch platforms...because their AI sucked a lot and got in the way of our business.

This is the fastest way to get fired as a vendor.

This is how it went down.
8:45 am- I got a notification our account was frozen for an unknown reason on the day we deliver client newsletters....hours before our deadline.

We don't miss deadlines at StartStak.ai. Ever.

10 min later while chatting with support, the support AI thought it was "GREAT, our account was suspended and said, 'we don't do compliance tickets, that's someone else'...in a happy chipper tone. I was PISSED. 🤬 

I asked them to call me....so I can talk to a live person. Nope.....just and AI professing to be a person. 

15 min later we are researching a different platform and started a free account. We grabbed our audience data.....and started onboarding making backup plans.

30 min later I got an email from the compliance team saying, "oh sorry, this was an error" with no explanation, no phone call. 

Meanwhile their support AI is asking if I want a discount. ☠️ 

NO. I AM GONE. Churned just like that after being a loyal paying customer for years. Scott said, "ya no, I built what we need in an hour, let's bounce".

You will hear a lot about Jack Dorsey cutting jobs because AI is awesome and replaces people. I think the worst place you can implement AI is in customer facing functions. 

I predict, CHURN is going to go way up for companies who use AI to interact with the their customers, prospects and customer facing suport.

Mark my words. Good news is we have new software to play with. 

We hit our deadline. 💪

How can we engage a community on what people are doing in AI? 🤔 

no like…where the rubber meets the road with your mind, your machine and your actual work? 

AI Show and Tell. Yep. 😃 

Like kindergarten, but BETTER because it is in a room full of Chiefs, where power meets purpose and we find our center focused on our individual missions.

You are probably reading everywhere that AI projects fail and “AI isn’t valuable” etc. Well, thats probably because there is a real problem in people understanding how to apply AI to their daily work. 

AI is not a search engine or a question and answer system- at all. AI is a system of engagement and play. These systems are fuzzy. Using AI is a skill, it takes practice and we are ALL learning.

Start with one. You. One use case and a problem YOU can solve.

A practical framework for AI and just about anything:
👉 What is the problem?
👉 How were you hoping to solve it?
👉 What was the AI tool, model, prompt and process used?
👉 What were the inputs?
👉 How was it applied?
👉 What was the outcome and why did it matter?

So, this is what we will be doing this Thursday at Industrious in Plano at 4 PM. 
📣 Calling ALL Dallas Chiefs, come learn with us in #AI so you can Lead On. Check the portal and sign up. Link in the comments.👇

Anyone in Dallas who wants to join this incredible community contact Kim Carpenter, PCC. The Dallas Ft. Worth community is in a race to have the HIGHEST engagement across all cities. We are just a little competitive. 😜 💚 

We got some Texas pride showin’ here ya’ll. 🤠

This feels like a full circle for me. 🔥 

I always loved my time at #Workday. The people there are top notch, professional and excellent. I met Steven years ago in the Dallas office.

He called last fall and said, "Liz, help me launch my company." I said, "Yep, that's what we do at StartStak.ai". 🥷🏻

StartStak + Porterhouse SLED became an integrated team to get that job done. Launch the company, while the team wraps up their jobs, do it fast, excellent with no mistakes! GO! 🏃‍♀️‍➡️ 

We have been in a dead sprint for the last months designing and operationalizing the company strategy, brand identity, product messaging, content, site, unique data and launching 6 campaigns simultaneously to hit the Workday SKO deadline. 🤯 

It has been awesome half crazy and a demonstration of our skills as a team who designs companies that are cohesive, Day 1. They already have pipeline!!

Porterhouse SLED is about to take the Workday public sector market by storm, with StartStak in their corner! 💜 

#Startup #Launch #NoPivots

Today, Porterhouse SLED, a Workday Adaptive Planning Services Partner, announced today its official launch. 🚀 

By introducing a new model for public sector finance modernization, they aim to dramatically reduce the time, disruption, and risk traditionally associated with budgeting and planning transformations.

Built exclusively for state and local government, higher education institutions, and water districts, Porterhouse SLED combines deep public sector domain expertise aligned to industry standards with AI-assisted implementation accelerators, to deliver solutions that address industry specific challenges.

The firm enters the market at a critical time. 
👉 Public sector finance teams are facing tighter budgets, 
👉 Heightened scrutiny from auditors and governing boards, 
👉 Workforce shortages
👉 Increasing compliance complexity

Most budgeting and planning solutions were designed for private-sector enterprises with far larger budgets and staffing capacity. 

This is where industry accelerators and AI-assisted delivery can drive efficiency and consistency to establish a new standard for the SLED industry.

Porterhouse’s leadership team is widely recognized for helping establish and scale Workday across public sector institutions nationwide.

Get in touch bids@porterhouse.ai or https://porterhouse.ai/

Workday Partners #PublicSector #HigherEducation
https://lnkd.in/gHYH53FW

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