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.

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

Stepping away from a traditional executive role can feel risky — especially when you’ve spent years building a career.

Four years ago, I was there myself, in a career transition, after decades of experience building new offerings, taking them to market, fixing businesses and starting up business units. 

Resources are scarce even in large companies and the politics….holy cow. ☠️

After many interviews being told I was overqualified, companies didn’t need “all that”, the run around, ghosting, and our “roles are narrower than what you do”…..I was SO FRUSTRATED. 😡

Eventually, I quit looking for a job and started to make my own. StartStak.ai now in its third year, is where my passion for entrepreneurship meets purpose.

I’m excited to lead an upcoming educational session for the Chief network for executive women who are exploring entrepreneurship as a potential next chapter, especially while in between roles.

In this session, I’ll share:

- How I transitioned to becoming a founder
- What I wish I had known before making the leap
- How to evaluate entrepreneurship as an alternative to corporate paths
- Practical guidance on early-stage business planning and go-to-market execution
- Managing your mind on the journey and avoiding burnout

At StartStak, we’re building an AI-native platform designed to help founders take any idea further, faster — and get to market with precision. Our mission is to broadly enable entrepreneurship, not just talk about it.

This session will be for leaders who are asking:

"What’s next — and could building something of my own be it?”

Chiefs, check the app and join me on the 28th at 12 EST. 

For anyone else interested who is not a Chief member, let me know and we will have another one of these events in the StartStak Arena soon!


#Entrepreneurship #CareerTransition #Founders #Leadership #StartStak #AINative #Chiefs


https://lnkd.in/gKXFeDmG

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

We are a global team. 🌎 

Team #StartStak, is a skills first company. The criteria I look for is you are the best at what you do. I really don't care where you live. 

"Back to the office" is for companies with real estate and leadership issues. I don't have either of those problems, but understandable, many companies do. 

Our team is based across many time zones including UK, US, Brazil, Pakistan, India, Canada, Nigeria and The Philippines - which will evolve as we grow. This is not about "labor arbitrage", this is about speed, precision and accuracy. 

StartStak operates by way of a meticulous follow-the-sun model that runs continuously across all time zones. Our software development, content, marketing, product, design and media teams all work in carefully coordinated handoffs across various projects and deliverables. This means progress doesn’t pause when one region logs off — it’s passed forward into another set of capable hands - like a business relay race. 🏃‍♀️‍➡️

Every single person uses #AI within their work, for their specific domain. However, everyone is Accountable, Responsible and in Control (from my TED Talk 3 years ago) of their work. This means, quality of the work is very high and each individual "owns" the work output. 

"AI did it", does not fly here. What we have learned is “AI-Slop” takes more time to unwind, so we take care of how AI is part of our daily work. 

Clear ownership, strong process, shared context, and deep trust in each other’s technical expertise allows StartStak.ai to produce the output of a company five times our size. 

This type of operating model allows for impressive efficiency, but only works because of the people who form our skills first team. When we hire, we are looking for unique talent, broad skills, the ability to context switch across many projects, operate independently, though we work as a team and make decisions together along the way. 

This has led to a culture of transparency, discipline, and respect. Teams have to think not just about their own work, but about what the next team needs to succeed. Our global design with the right people in the right jobs is an extreme advantage that includes diverse perspectives.

As we continue building StartStak — and the systems we design for early stage founders — this follow-the-sun operating model matters because founders have zero time, and we really understand this. ⌛ 

While Silicon Valley is working 9-9-6 and venture backed companies have a DoorDash budget because "in person" in an office is required, we are doing something different. 

We don't always get it right, but this model is proving to be what works for us. Resilient companies are built by teams with high trust, accountability and who know how to "move together" for whatever the challenge of the day is. 

There are a lot of challenges to building a successful company. If “team issues” isn't one of them, you are many steps ahead in whatever it is you’re trying to do. 

#Startup

AI isn’t a side project anymore - it’s becoming the operating system of modern companies. 

AI is at the heart of everything we do at StartStak.ai, from day 1. This is what it means to be an #AI-Native.

I’m excited to be joining Tadas Jucikas, PhD (CEO, Genus AI) and Serge Gershkovich (Head of Product, SqlDBM) for an upcoming panel conversation with DataCamp on what it actually takes to build an AI-native enterprise.

We’ll go beyond tools and hype to talk about:
👉 How org structure needs to change for AI-first execution
👉 Where leaders get stuck when moving from experimentation → impact
👉 What not to do when scaling AI across teams

Whether you’re building from scratch or transforming an existing business, this is about turning AI ambition into real outcomes.

📅 Feb 11, 2026- 11AM EST
🎙️ Panel-style discussion

Build An AI-Native Enterprise 
Register here https://lnkd.in/g9ks_Gr7
Hope to see you there 👋 

Rhys Phillips Richard Cotton

#AINative #Leadership #AITransformation #Founders #Startups #EnterpriseAI

Product–market fit is one of the most talked-about concepts in SaaS, yet one of the least understood in practice. 

Everyone has metrics for what success looks like after PMF, but almost no one talks honestly about what it feels like while you’re in the thick of it, before the metrics begin.

We’ve partnered with SaaStock to run a qualitative, multi-cohort study to observe founders living inside PFM. By really understanding “the messy middle”, better frameworks can be built to guide founders through the most difficult part of the company building journey.

Valuable insights are already emerging from our 4 cohorts; the Seekers, Survivors, Scalers and the Stranded that are challenging common industry narratives. 

From our Survivors group, the early insights from founders who made it through the ‘Messy Middle’ have a few things in common:

- PMF didn’t feel like a breakthrough. It felt like constraint.
- The riskiest phase wasn’t failure, it was when it’s ‘almost working’.
- They listened to customers, but filtered requests carefully.
- Patterns emerged before metrics. Metrics came later.
- Focus wasn’t optional. It was survival.
- False positives looked like momentum without repeatability.

And for this cohort, they report, there is never “comfort”. 

Post-PMF isn’t easier — just quieter and heavier, with more responsibility that looks and feels like stewardship.

If you would like to join this cutting-edge industry research, click the link below or DM me: 
https://lnkd.in/gU48Hvc4

#PMF #SaaStock #ResearchInitiative #StartStak #MessyMiddle #Entrepreneurship #Business

If you’ve been watching the AI conversation from the sidelines, this is your moment to step in.


I am excited to be leading the Dallas Chief #AI Series along with Priya Reddy.

We designed these two sessions for leaders who don’t want another technical deep dive or high level overview — they want clear guidance, confidence, and thoughtful discussion about how AI actually shows up in leadership and work.

Our first session, AI Foundations for Leaders, is a smart, grounded entry point for new Chief members who want to learn alongside peers, ask honest questions, and leave with practical ways to lead through change.

No jargon. No hype. Just leadership, perspective, and new connections across a powerful community of women.

📍Dallas | January 29
Industrious Plano, Plano
4 PM to 7 PM CST

If you’re new to Chief — or considering joining — this is a great place to start. Ping our community manager Kim Carpenter, PCC. She has an incredible year planned!

https://lnkd.in/gyB9eZZR

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Leslie Greenwood

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