The Rise of Non-W2 Leadership: Why More Executive Women Are Rethinking Traditional Roles
Wednesday Women
59:26
For years, success followed a familiar script: land the W-2 role, climb the ladder, stay the course. But for many executive women, that model is starting to feel… incomplete.
Today, more leaders are exploring non-W2 paths — entrepreneurship, fractional roles, advisory work, portfolio careers, and independent leadership — not because they’re stepping back, but because they’re stepping into more aligned, sustainable ways of leading.
In this Wednesday Women conversation, we’ll explore:
- What’s driving the non-W2 shift
- How influence looks different when your work spans multiple organizations
- Why the way we “screen for credibility” can unintentionally narrow who gets access to rooms, opportunities, and visibility
- How women at the top are redefining power, impact, and career longevity on their own terms.
Speakers
Melissa Moody
Host & Cofounder @ Wednesday Women
Melissa Moody is an entrepreneur and full-stack marketing executive, and the co-founder of Wednesday Women, a community and executive membership dedicated to amplifying and supporting extraordinary women leaders. She advises a select portfolio of growth-stage companies on marketing strategy, leadership, and execution, and brings more than two decades of experience building clear, user-centered growth strategies across startups and global organizations. A passionate advocate for fast, frictionless products and remote work, Melissa brings a human-centered lens to innovation, leadership, and community-driven growth as she moderates today’s conversation.
Leslie Greenwood
Cofounder @ Wednesday Women
Leslie Greenwood is the Co-Founder of Wednesday Women and Founder of Chief Evangelist Consulting, guided by a core belief that community isn’t a tactic—it’s a force. Through Wednesday Women, she amplifies executive women as their real, remarkable selves, building both a public platform for visibility and a private membership for deeper connection, support, and shared momentum. With 20+ years in customer-facing leadership, Leslie helps companies design community strategies rooted in trust, value, and authentic engagement.
Ellie Wu
Founder & Executive Advisor
Ellie Wu is the founder of CSuiteCX, working with $10M-$100M ARR B2B SaaS companies when board pressure exposes cracks in customer strategy and the right read determines growth, funding, or valuation. After being the operator in that seat and advising hundreds of portfolio companies across different market cycles at Insight Partners, she built an independent practice for the freedom to solve problems traditional roles couldn't and capture the unlimited upside that comes from fully owning her expertise.
Ashley Stamps-Lafont
VP, Customer Success @ QuotaPath
Ashley Stamps-Lafont is the Founder of The Success Rx, an executive coach, advisor, and angel investor — proof that leadership doesn’t have to live in a single box. She has built and led go-to-market and customer organizations across startups and global companies scaling from roughly $5M to $1B+ ARR, and now brings that operator’s perspective to leaders navigating pivotal career and leadership transitions. Known for going deep with frontline teams one day and advising founders and executives the next, Ashley brings equal parts energy, operational rigor, and strategic clarity to the leaders she works with. She is also the creator of the Women of Pavilion Advice Clinic, which convenes experienced GTM leaders to prepare executive women 1:1 for high-stakes recruitment conversations. Her work centers on helping leaders build careers that create impact across organizations, not just within a single title.
The Rise of Non-W2 Leadership: Why More Executive Women Are Rethinking Traditional Roles
59:26