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

Time & Relationships Consulting

While I excel in full-time roles, with 20 years in revenue-generating positions and an extensive network, I’m also available for fractional consulting to help companies drive revenue growth, build partnerships, and leverage the power of connections and content.

𝐀 𝐟𝐞𝐰 𝐩𝐫𝐨𝐣𝐞𝐜𝐭𝐬:
• Facilitated collaboration between podcast production companies, B2B SaaS marketing teams, and a SaaS employee advocacy business to enhance content marketing, sales engagement, and podcast performance
• Strategic partner for a business intelligence and marketing analytics platform in the legal industry
• Created a sales strategy for a startup tackling restaurant food waste with order management.
• Developed a $125k/year sponsorship model for a student-athlete company.

𝐋𝐞𝐭’𝐬 𝐜𝐨𝐧𝐧𝐞𝐜𝐭 𝐭𝐨 𝐝𝐢𝐬𝐜𝐮𝐬𝐬 𝐡𝐨𝐰 𝐈 𝐜𝐚𝐧 𝐡𝐞𝐥𝐩 𝐲𝐨𝐮𝐫 𝐛𝐮𝐬𝐢𝐧𝐞𝐬𝐬 𝐠𝐫𝐨𝐰.

Principal

I’ve sold podcast ads and sponsorships, managed three podcast listening platforms, engaged with hundreds of podcasters, and worked for an AI company deeply connected to the podcasting industry.

With this unique perspective and experience, I consult and coach businesses to launch their own podcasts and existing podcasters looking to:
1️⃣ Expand their Distribution
2️⃣ Grow their Audience
3️⃣ Monetize effectively
4️⃣ Build their content into a brand and business
5️⃣ Overcome fears, reframe limiting beliefs, and develop a success mindset

𝐑𝐞𝐚𝐝𝐲 𝐭𝐨 𝐭𝐫𝐚𝐧𝐬𝐟𝐨𝐫𝐦 𝐲𝐨𝐮𝐫 𝐩𝐨𝐝𝐜𝐚𝐬𝐭 𝐢𝐧𝐭𝐨 𝐚 𝐩𝐨𝐰𝐞𝐫𝐟𝐮𝐥 𝐛𝐫𝐚𝐧𝐝? 𝐋𝐞𝐭’𝐬 𝐜𝐨𝐧𝐧𝐞𝐜𝐭.

Podcast Coach & Consultant

As a podcast industry veteran, I bring immense value through my deep understanding of the hard work involved in creating a successful podcast. I offer energy, knowledge, and experience to help podcast hosts craft compelling episodes with engaging and share-worthy content. I’m also passionate about promoting the podcasts I appear on across my social channels to help amplify their reach.

𝑇𝑜𝑝𝑖𝑐𝑠 𝐼 𝑆𝑝𝑒𝑎𝑘 𝑂𝑛:
𝐓𝐡𝐞 𝐀𝐫𝐭 𝐨𝐟 𝐏𝐨𝐝𝐜𝐚𝐬𝐭𝐢𝐧𝐠:
With years of experience running multiple podcast platforms, I dive into the strategies, tools, and insights that drive podcast success and growth. I share actionable tips for creating standout episodes and growing a podcast audience.

𝐍𝐞𝐭𝐰𝐨𝐫𝐤𝐢𝐧𝐠: 𝐓𝐡𝐞 𝐏𝐨𝐰𝐞𝐫 𝐨𝐟 𝐑𝐞𝐥𝐚𝐭𝐢𝐨𝐧𝐬𝐡𝐢𝐩𝐬
"Life is about Time & Relationships." I provide practical strategies for effective networking, building lasting relationships, and thinking long-term to foster success both professionally and personally.

𝐁𝐫𝐚𝐧𝐝 𝐁𝐮𝐢𝐥𝐝𝐢𝐧𝐠 𝐟𝐨𝐫 𝐒𝐮𝐜𝐜𝐞𝐬𝐬:
Drawing from over a decade in media, I offer actionable insights on leveraging brand-building techniques to create new opportunities and stand out in today’s competitive marketplace.

𝐆𝐫𝐢𝐭 & 𝐑𝐞𝐬𝐢𝐥𝐢𝐞𝐧𝐜𝐞: 𝐌𝐲 𝐓𝐮𝐫𝐧𝐚𝐫𝐨𝐮𝐧𝐝 𝐒𝐭𝐨𝐫𝐲
Everyone faces challenges, but how you respond defines your journey. I share my personal story of career burnout and mental health challenges and offer valuable lessons on developing resilience in the face of adversity, helping to normalize stigma, and help others feel less alone.

𝐌𝐞𝐧𝐭𝐚𝐥 𝐇𝐞𝐚𝐥𝐭𝐡 𝐌𝐚𝐭𝐭𝐞𝐫𝐬:
Having navigated high-pressure corporate environments and personal growth, I speak openly about mental health. I aim to provide support, inspiration, and actionable advice for those struggling with their own challenges.

Podcast Guest

RevGenius

Always curious to improve my skills, learn from others, and be a part of a network to grow. 
As a member of RevGenius, I demonstrate my desire to learn and my growth mindset.

RevGenius is a group of revenue-generating sales and marketing professionals brought together to learn, share, support, and grow with each other.

Member

Partnership Leaders

As a member of Partnership Leaders, I continue to elevate my strategic thinking and connections leading to solutions and be a part of a community to turn to for help and learning. Always be curious and drive revenue and value.

Partnership Leaders is the industry association for Partnership/Channel/ Alliances/Business Development leaders. Their mission is to elevate the role of partnership leaders at their companies and provide a vibrant online community through virtual events, curated professional networking opportunities, and educational resources to drive success for our members.

Podcast(H)er

With years of experience supporting podcasters and small business owners, a unique perspective, and experience with podcasting, I consulted with Podcast(H)er to assist in creating a platform for female business owners serious about utilizing podcasting as part of their overall business engine.

If you're a female podcaster, looking to learn, grow, and monetize, check out the Podcast(H)er community
https://www.podcasther.com/a/2147831026/uXaXhApi

Head of Relationships

castmagic

As a relationships-focused revenue generator with experience running three successful podcast platforms, I joined an AI-focused SaaS startup to bring a human-centered approach to a technology-driven space.

As Head of Relationships and Humanization Consultant, I helped shape the company’s identity to feel more approachable and personal in an increasingly automated world. By creating conversations and fostering connections, I made customers want to engage with us rather than just use the product.

Joining in the third month, with MRR at $1,000, I served as the ultimate utility player:

𝗣𝗮𝗿𝘁𝗻𝗲𝗿𝘀𝗵𝗶𝗽𝘀 => Evaluated tech integrations, partnered with aligned companies and created co-marketing webinars.

𝗦𝗮𝗹𝗲𝘀 => Led direct outreach, demos, webinar series, event participation, podcast guesting, and affiliate/referral program management.

𝗖𝗼𝗺𝗺𝘂𝗻𝗶𝘁𝘆 𝗮𝗻𝗱 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 => Grew a Slack community to 1,400+ members, led onboarding and weekly office hours, developed training resources, and improved product adoption while reducing churn.

Through our SaaS AI platform, I enabled Small Businesses (SMB) and Mid-Sized companies to save time, grow revenue, and maximize their content output. In our first year, I contributed to growing revenue from $0 to $1M ARR, scaling the customer Slack community to over 1,400 members, and successfully launching an affiliate/referral program.

𝗠𝘆 𝗺𝗼𝘁𝘁𝗼:
"Life is about Time & Relationships. It's about opening connections and conversations, as you never know where they may lead."

𝗧𝗵𝗲 𝗿𝗲𝘀𝘂𝗹𝘁:
I created a customer-first environment that humanized our AI platform, building brand equity through authentic connections, fostering community growth, and driving revenue while increasing adoption and decreasing churn. It’s the little things—those human touches—that made our success possible.

Maple Media

I was hired by the founder to build out new revenue streams, expand product offerings, explore licensing opportunities, and grow paid subscription revenue for a mobile app/subscription/advertising platform. I was enthusiastic to learn multiple new products and industries, think strategically about how to build revenue, and expand my business development and partnership skills, 

During my tenure, I learned about the podcast industry, and grew the revenue from $52k/year to $1M+/year, expanding the product offering and growing our audience. My success was recognized as I was enlisted to be a judge for a leading podcast award.

I established 20+ strategic partnerships in the legal and accounting industries, reaching 10% TAM, and evaluated technical product integrations and a reseller channel.

Sourced 8 licensing contracts with leading financial firms to improve data and content for our financial product and evaluated a product offering for a new revenue channel.

Director of Global Sales, Business Development & Partnerships

Freebird 

I was hired by the founders to lead the non-endemic revenue strategy for a rideshare rewards platform. I believed in the mission, was energized by the culture, and had an opportunity to utilize my advertising background in a new and unique medium.

I had great success opening conversations with brands to build out the roadmap for monetizing the platform. Recruited partners in the Fintech space and other rewards platforms to co-market to acquire 1000s of new users, coming in 20% below marketing CAC. Negotiated a 6-figure tactical deal with an NHL hockey team. Assisted in adding restaurants and retailers to the endemic portion of the platform. 

I was able to demonstrate my ability to be a resourceful self-starter and tenacious problem-solver, willing to roll up my sleeves to meet the needs of a startup beyond the duties hired for. I learned about the engineering challenges of a startup built on the foundation of other companies. 

Unfortunately, due to Covid-19, the company was forced to close operations.

Director Of Sales And Business Development

Jungle Creations

I was approached to open the West Coast office for an award-winning UK-based startup, leading the operations and sales initiatives. The opportunity to take my positive can-do attitude, track record of consistently meeting or exceeding sales performance goals, and be incredibly hands-on for a startup was a great growth challenge for me.

I was focused on building revenue and brand equity on the West Coast, working with brands and agencies to drive better business outcomes by leveraging our best-in-class video production, creating compelling video content, and utilizing our massive scale for distribution. 

During my tenure, I established a warm, collaborative office culture, generated over 40 RFPs valued at over $3M, and closed multiple deals ranging from small to 6-figure, by creating new business and existing relationships. Operations were closed unexpectedly due to platform changes that severely impacted the company's overall monetization.

Director of US Sales & Business Development - West Coast

CBS Corporation

With CBS separating its radio division, our team joined the CBS Radio organization. I continued my growth as a consultative seller and transitioned from a national digital seller to a strategic role on the Altitude Integrated Sales Group, utilizing all of CBS Radio's assets to assist brands and agencies with solutions to meet their goals.

I continued to gain new business while growing existing accounts. Our podcast business was in the early stages, so I was able to help build out the framework, create proprietary reporting, become a subject matter expert, establish new relationships, and be the lead seller on the team for the West Coast in 2017.

Our team launched a complex longer sales cycle product, branded content, and through an existing relationship and a new one, I was able to sell 2 strategic 6-figure deals. One a 6-part 60+ minute web series that involved the complexity of production, talent, and advertising.

As CBS Radio was being sold to Entercom, I was approached to open the office for a UK-based startup in the social content/branded content space and took the challenge to help them establish a West Coast office.

Director, Strategic Partnerships – West Coast

Eventful was acquired by CBS Local in July 2014. Being naturally curious and seeing the opportunity for growth, I stayed with the company as it provided me the opportunity to expand my advertising knowledge and skillset, offering more complex and strategic solutions (experiential, native, podcasting, digital).

In 2015 I was the #1 sales rep on the team, with $800k+ revenue obtainment.

Account Director- National Sales

Eventful

I joined former co-workers at a startup with the opportunity to join a fast-paced, high-growth company to make a giant impact by generating new business and expanding my knowledge by learning a unique solution around data, email, and content.    

In the 2 years there, before we were acquired by CBS Local, I achieved a 22% close ratio. Developing relationships with brands directly and advertising agencies, I was the first seller to generate new business in 3 verticals (Automotive, Consumer Package Goods, and State Lottery). I successfully closed business with restaurants, CVBs, Retail, Attractions, Events, Beauty, and Electronics.

I learned how to overcome the challenges of being a small company in a competitive advertising space and found success by understanding agency and company structures, identifying key decision-makers and budget owners, and engaging with them continuously to foster relationships by traveling to conferences and across the western states for meetings and presentations. I constantly increased revenue and closed 6-figure long-sales cycle deals.

Account Director

Revenue Generator 💰│ #Partnerships Builder 🧱 │ People Connector 🤝 │ #Podcast Consultant 🎧 │ Lifelong Learner 💡 │ #opentoconnect

𝐖𝐡𝐚𝐭 𝐝𝐫𝐢𝐯𝐞𝐬 𝐦𝐞?
Building meaningful connections, staying curious, and creating opportunities that make an impact. I’m inspired by the people I meet, the ideas we share, and the growth we can achieve together. 

𝐌𝐲 𝐒𝐭𝐨𝐫𝐲
From growing up with Chicago roots to earning my marketing degree at USC (Fight On✌️), my journey has been shaped by an entrepreneurial spirit and a passion for helping others thrive.

I’ve gone from exceeding sales quotas and managing teams at Yahoo! to leading partnerships at startups, where I developed innovative revenue streams and built communities that drive business growth. Along the way, I’ve earned a reputation as "the guy who knows someone" or "the guy with the answers."

𝐇𝐨𝐰 𝐈 𝐂𝐫𝐞𝐚𝐭𝐞 𝐈𝐦𝐩𝐚𝐜𝐭:
• Revenue Generation: Designing and executing creative go-to-market strategies, partnerships, and programs that open up new revenue streams.
• Community-Driven Growth: Building customer communities that drive sales, reduce churn, open partnership opportunities, generate content, and build advocates. 
• Customer-Focused Solutions: As Head of Relationships, I listen to people, connect them to solutions and opportunities, and channel their feedback into product improvements, partnerships, and brand advocacy.

𝐖𝐡𝐲 𝐂𝐨𝐧𝐧𝐞𝐜𝐭𝐢𝐨𝐧𝐬 𝐌𝐚𝐭𝐭𝐞𝐫:
Life is about Time and Relationships—you never know where one conversation today might lead. Building authentic connections is at the core of everything I do, both personally and professionally. 

Take whichever cliché you want, but I love them all:
• “Success in business is all about relationships. It's about trust, respect, and loyalty.” – Jack Welch
• “Business is all about relationships. Build them, nourish them, and always be honest and transparent.” – Richard Branson
• “You can never go wrong by investing in relationships.” – Gary Vaynerchuk


𝐖𝐡𝐞𝐭𝐡𝐞𝐫 𝐲𝐨𝐮’𝐫𝐞 𝐥𝐨𝐨𝐤𝐢𝐧𝐠 𝐭𝐨 𝐢𝐦𝐩𝐥𝐞𝐦𝐞𝐧𝐭 𝐚 𝐫𝐞𝐯𝐞𝐧𝐮𝐞-𝐟𝐨𝐜𝐮𝐬𝐞𝐝 𝐜𝐮𝐬𝐭𝐨𝐦𝐞𝐫 𝐜𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲, 𝐞𝐱𝐩𝐥𝐨𝐫𝐞 𝐩𝐚𝐫𝐭𝐧𝐞𝐫𝐬𝐡𝐢𝐩𝐬, 𝐥𝐞𝐚𝐫𝐧 𝐚𝐛𝐨𝐮𝐭 𝐩𝐨𝐝𝐜𝐚𝐬𝐭𝐢𝐧𝐠, 𝐨𝐫 𝐞𝐱𝐜𝐡𝐚𝐧𝐠𝐞 𝐢𝐝𝐞𝐚𝐬, 𝐥𝐞𝐭’𝐬 𝐭𝐚𝐥𝐤. 
𝐎𝐧𝐞 𝐜𝐨𝐧𝐯𝐞𝐫𝐬𝐚𝐭𝐢𝐨𝐧 𝐜𝐨𝐮𝐥𝐝 𝐨𝐩𝐞𝐧 𝐭𝐡𝐞 𝐝𝐨𝐨𝐫 𝐭𝐨 𝐬𝐨𝐦𝐞𝐭𝐡𝐢𝐧𝐠 𝐚𝐦𝐚𝐳𝐢𝐧𝐠.

---

When not succeeding at work, you can find me hiking, deep in self-growth discovery, going to a concert or sporting event, traveling, or kicking back with a drink—always with a smile on my face (or smirk). 

MB= ENTJ
DISC= DI (Initiator)
Enneagram= 3 (performer)
WHY.os = Better Way ➢ Clarify ➢ Make Sense

Greg Wasserman

Video is the topic right now.
Someone helped me understand a nuance to the problem I haven't heard yet.

Big thank you Doug Downs, for the great conversation
And for pointing out something I hadn't heard mentioned.

Doug edits 𝘢𝘶𝘥𝘪𝘰 and 𝘷𝘪𝘥𝘦𝘰 differently for his clients. 
Not just slightly. 
Entirely with the 𝗹𝗶𝘀𝘁𝗲𝗻𝗲𝗿 𝗮𝗻𝗱 𝗺𝗲𝗱𝗶𝘂𝗺 𝗶𝗻 𝗺𝗶𝗻𝗱.

He knows an audio-only experience is consumed differently from video. 
Different audience. Different behavior. Different expectations.

So he puts in the extra time to craft both versions
🎥 A video that fits how people watch. 
🎧 An audio edit that fits how people listen.

It takes more work. 
But it delivers a better experience. 
And when you create for 𝘩𝘰𝘸 𝘱𝘦𝘰𝘱𝘭𝘦 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘤𝘰𝘯𝘴𝘶𝘮𝘦, your engagement and metrics follow.

Everyone's talking about Video Video Video.
But no one's talking about ensuring you're editing the two for their appropriate mediums.

This was the first time I’d heard someone say they consciously do this.

I've heard that 50% of those watching the video are only listening.
Few are talking about how they are editing their content to ensure this.


Steve Stewart — curious what you’re seeing from editors in the Podcast Editors Academy. 
Are others starting to take this approach?

Relationship Generator 🤝 │ Partnerships Builder 🧱 │ Community Cultivator 🌱 │ Revenue Accelerator💰 │ Podcast Consultant 🎧 │ Humanization Strategist 🤖 │ Open to Connect 🙋🏻‍♂️

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