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

Elizabeth McCalley.eth 🦋

StartStak.ai

An AI-Native firm with expertise in emerging technology enabling growth through new markets and buyers.

AI services are focused on business strategy & go to market, defining business value for buyers, routes to market, launching new products and portfolio (re)positioning.

CEO & Founder

Pavilion

CEO Member & DFW Chapter Leader

Panzura

Repositioned the company's software portfolio into a new market to capture higher value buyers focused on analytics. Developed corporate messaging aligned to CEO industry imperatives, and advised on a go-to-market strategy engaging alliances & tech ecosystem partners to accelerate growth. Engaged with analyst firms such as IDC and Gartner to gain alignment on market approach and define value for new line of business buyers of analytics and insights.

CRO Advisory- Vice President of Strategy & GTM

Salesforce

-  Established business strategy for business unit start up; sales strategy and Go-To-Market for new $1B channel within Salesforce enabling outsourcing providers of IT, Horizontal and Vertical digital process services. 
- Defined market, process service types & scope with near- and longer-term priorities.
- Identified key obstacles and barriers to success. 
- Defined TAM and financial requirements/resources for GTM team to operate successfully.

RVP New Business Unit Startup: Industry Portfolio Executive

Led partner sales team for Healthcare and Life Sciences industry vertical for GSIs & SI partners. Drove 229% of plan for new logos, resulting in 35% YoY growth, and achieved $218M in ACV, marking 20% YoY growth. 67% partner engagement and a 13% YoY growth.
- Salesforce FY21 Peak Performance Club Winner
- Led First Salesforce Chicago Marathon Team for the National MS Society, Raised 71K

RVP Partner Sales Alliances, Healthcare & Life Sciences

Workday

- 125% of plan. National Sales Team for Healthcare ERP, $50M Revenue Closed
- New business development for enterprise sales of Workday’s ERP platform 
- Buyers: CFOs, CHROs, CIOs, COOs and SVP SCM
- Engaged and created value for Workday alliance partners aligned to market goals.
- Built 50M in pipeline. Closed 12M TCV with the largest post-acute care organization in 8 months.

Sr. National Account Executive, Healthcare Key Accounts

- Corp Strategy: Led cross functional strategic projects to guide product management and sales teams to bring Watson Health analytics offerings to market.
- Analyzed and documented market requirements for cloud industry solutions within Life Sciences Real World Evidence and Value Based Care, incorporating both payers and providers.
- Created strategy framework for Life Sciences product managers responsible for business analytics & insights offerings.
- Defined market requirements and buyers of $1B analytics solution area of Real World Evidence (RWE). 
- Established point of view for the application of emerging technologies in the healthcare market including cognitive, interoperability, blockchain and cloud platform data services.

Watson Health Market Strategy & Development, Value Based Care & Real World Evidence 

- Led large cross functional team to create strategy, product and solution requirements as well as Go-To-Market for Watson Health’s data platform-as-a-service. 
- Developed use cases for data and analytics services targeted at healthcare and life sciences buyers.
- Led competitive market analysis, evolving business requirements, market opportunity sizing and established points of competitive differentiation for the Watson Health Cloud Platform.

Sr. Offering Portfolio Manager- Watson Health Cloud

- Led IBM’s Global Healthcare Cloud Strategy with responsibility for making recommendations to capture solution selling market opportunity in healthcare for various business models.
- Developed healthcare market messaging, created seller enablement assets and client facing communication for multiple cloud based industry solutions. 
- Drove 75M+ in revenue for cloud based solutions supporting IBM regional healthcare field teams. 
- Contributed research and writing for several IBM Healthcare Industry papers

Global Healthcare Industry Solutions Sales Executive

- Managed an enterprise Business Analytics Software team to drive LOB sales across 28 large accounts. Example clients: Exxon, Pepsi, American Airlines, Sprint, USAA, and Walmart. 
- Rebuilt and refocused team by setting sales goals, forecasting management, sales process discipline, structured call planning as well as on-boarded 
professional hires into IBM. 
- Developed 50M in new pipeline in 6 months positioning key wins at Sprint, USAA, and Exxon. 
- Gained knowledge of advanced analytics and cognitive principals such as pricing elasticity, market basket analysis, process improvement and consumer insight/intimacy.

Enterprise Sales Manager- Business Analytics Solutions

- Led 45+M in competitive new logo B2B enterprise software sales, developing new market in Texas.
- Strategic focus on collaboration, analytics, data management, security, application and data integration. 
- Led several “First-in-Industry wins” at national accounts like Tenet and MD Anderson.
- 2008 (108%, 21% YTY Growth) 2009 (304% of FY 399% YTY growth) 2010 (172% of FY 220% YTY growth) 2011 (130%), 100% Club Award 2009, 2010, 2011, IBM National Eagle Award

Sr. Software Account Executive- Healthcare

- Responsible for IBM B2B enterprise sales to The Texas Medical Center in Houston; executive relationships, leading complex solutions and consulting services sales. 
- Grew territory 103% exceeding revenue and signings targets. 2006 (118%), 2007 (114%), (2006) IBM VP Award, Pacesetter, 100% (2005), 111% (2004), 100% (2003), IBM Leadership Award, IBM Rookie of the Year

Healthcare Client Account Executive

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

I have one heck of a partnership to announce today! 🥳

I care deeply about two things: doing meaningful work, and making the path easier for others to be successful too. 🤝

#Founders who are choosing to build a business from nothing already won, just by making that brave choice. The $0-3M path is very hard, even for founders with significant experience.

There is a pattern in the market whereby many early stage companies get stuck in what we call, "The Messy Middle". Peter Walker posted an excellent picture of this on X last week…..and I annotated it! 😃 (Hope that’s okay).

The Messy Middle is that really uncomfortable and unpredictable stretch after an MVP and before “traction” or stabilizing metrics investors love like NRR, LTV, CAC, pipeline velocity that tell the clear story called "Product Market Fit" (PMF). 

PMF is the most important milestone of an early stage company. Waiting list sign ups don’t count!

There are no clear startup industry metrics nor accepted frameworks for this part of the early company journey, because there is little empirical data. 

Navigating this part of the journey feels like a mirage in the desert.....or a gauntlet one survives. 

I believe there are valuable patterns and insights we can uncover from qualitative information, so we can take the guess work out of getting to PMF.

As such, I am thrilled to announce StartStak.ai will be leading new ground breaking research in partnership with SaaStock, the leading global events company for early stage founders. 💜 🩷 🤝 

Our collaborative research initiative is called: "The PMF Gauntlet: A Qualitative Deep Dive into the Founder’s Journey from Hypothesis to Market Pull".

#StartStak will be leading first party research on four cohorts of founders across different stages of their PMF journey, gathering valuable, qualitative insights around how they navigate ambiguity, evaluate opportunity, and make important calls when the path forward is as clear as mud.

Our shared goal is to build a practical, evidence-based framework to develop new tools for this often elusive phase of getting to market stability. In my heart of hearts, I am a researcher and this just fits with everything we are about!

This work is a natural extension of both StartStak’s mission and SaaStock’s commitment to supporting early-stage teams led by Alexander Theuma. We are thrilled to be working with Chloë Dormand, David Umpleby and the team!

Take a look at #SaaStock here: https://www.saastock.com/

#StartUps #PMF #Entrepreneurship

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

Our stealth founders…🥷

We LOVE them and we are in on it:

👉The careful planning 
👉The excitement 
👉The “I can’t believe we are really doing this 😳….FINALLY🥳”.
👉The consternation.😅
👉The calculating risk. 

That last part is why they call us. 📞

When you are self funded, are under crazy time pressure and can make no mistakes implementing your new company, the only company you call is StartStak.ai.🙌

We have a LOT of Gmail addresses, crazy weird data on our founder buyer journeys and it is super fascinating. 

These founders have no existing websites, you cannot find the name of their company on LinkedIn and lots of other clues that they are in serious stealth mode. 

It’s all greenfield and a super fun ride. We have a number of teams like this now…planning. 

We have the darkest of the dark funnels.

#Stealth #Founders #Sprint

graphical user interface, text, application, chat or text message

The center of the world for the future of financial services will be built in Dallas!

Welcome to Texas, Coinbase! 

The largest U.S.-based crypto exchange has chosen the Lone Star State as its new home, a strong signal that Texas is now the hub of digital-asset innovation.

We’re proud to see more industry leaders planting roots here!

🦃 Happy Thanksgiving! 

This is one of my favorite holidays of solid cooking and spending time with my family.

It is also a good time to pause to appreciate all the people who make StartStak.ai possible. 🩷 

I am grateful for the early stage founders who trust us and show up every day with courage and conviction to do the work.

Our partners who work with us on innovative ideas and breaking ground on things that have never been done before. 🙌 

And the people on this team who bring excellence every day - the early mornings and late nights, the expert work and process discipline, the problem-solving, the moments of creative breakthrough, and all the messy parts in-between.

Building anything meaningful is a human first effort.

I hope today brings you all good rest, great food, and the chance to be present with the special people (and pets) in your life. Cheers from Harvey Cat. 💜

Thank you!

#Thanksgiving #StartStak #Family #Friends #Holidays

On Saturdays, I work more than any other day of the week, uninterrupted. 


This morning, I am thinking about the word "architecture". In the post AI era, architecture is not about how technology fits together. An AI-Native architecture is also people and process, but unlike our usual understanding.

Digital transformation is evolving more quickly than we understand at this point. I think in the future (soon), architecture for AI-Native companies will be discussed as the "company architecture" because #AI is doing work along side, and in collaboration with people, who have machine specific expertise.

Fact: 👉 You CANNOT scale down architecture, only up. 

This is the reason monolithic applications have a hard time going down market to support tiny companies. Their services are not composable in a way that is consumable for the "long tail" of the market. This is why companies like AWS can support tiny workload and mass scale at the same time. This is also why Microsoft and Salesforce are in deep trouble- among other reasons. 

As it relates to AI-Native companies and their people....

In traditional companies, jobs are containers. Fixed scope. Clear edges. One person, one box on the org chart. Your polymaths might get two or three.

AI‑native companies don’t work like that.

In AI-native companies, a person’s “role” is less about a function and more about a surface area of responsibility. They range across product, ops, support, strategy—wherever the problem lives. Where their knowledge ends, they extend themselves with AI. Research, drafting, analysis, coordination, even parts of execution are offloaded, multiplied, mirrored.

This approach helps avoid waste, bloat and unnecessary spending provided these people are deeply skilled in how they work, as well as their edges.

In our case, the output of one person at StartStak.ai isn’t 1:1 with a normal FTE. It’s closer to a small team—five, ten people’s worth of motion—depending on how far they lean into the supermodels and advanced tools.

That’s why the question “How many FTEs do you have?” misses the point. It assumes a world where people, process, and technology are separable and scale linearly. 

In an AI‑native "company architecture", technology is also like people. It thinks with you, works beside you, and erases the old math and myth of scale.

Headcount is the wrong unit.
Capability is the right one.

Our unit economics are going to be a thing to study. I am excited for that future. 

#AI-Native #StartStak #Leadership #BreakingBoundaries #NoRules

As a reminder, technology is not innovation. 🚫 

Innovation is a new idea, a way of solving a problem or doing something differently. Usually, innovation is born from constraints and testing limits.

Some of the best innovations do not even use technology at all. 

There is a term from psychology that applies here called "functional fixedness". 

What is that?
👉 Functional fixedness is a cognitive bias that causes people to see an object only in its traditional or most common use, limiting their ability to find new solutions to a problem

I think it extends beyond only objects to complex concepts as well.

What I see in the #startup space is a lot of this exact problem. 
👉 The same business plans, business models and GTM strategies 
👉 The same playbooks for growth
👉 The same formulaic pitch decks, competitions and the investor flywheel
👉 The same boring ideas of what successful founders need to "have" and "be" in order to be successful

The #founders who are the innovators, never get stuck on "one thing". By definition the most talented founders are those with new ideas and can get them done, 👉  no matter what. 

AND...the craziest part, is that #investors, who are naturally risk adverse, often cannot see them, because of "functional fixedness". 

This is the literal definition of an "innovator" spoken by the great Thomas J. Watson.

“Follow the path of the unsafe, independent thinker. Expose your ideas to the dangers of controversy. Speak your mind and fear less the label of 'crackpot' than the stigma of conformity. And on issues that seem important to you, stand up and be counted at any cost. ”

I have some crazy ideas alright. 

Our clients who love us do too. This is why we resonate and do 10 impossible things before breakfast building new companies. 🐛 

Happy Monday ya'll.

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