
When the Ladder Has No More Rungs, Here's What to Do, with Natalie Benamou
What if the thing nobody prepares you for is not the hard climb to the top - but the moment you get there and realize there is no next rung? You have done everything right. You have the title, the track record, the team. And you look up and the ladder ends. Today's guest built an entire network for the woman in that exact moment - and she is here to tell you that the ladder running out is not the end of the story. It is the beginning of the most interesting chapter you have ever written.
SUMMARY & GUEST INTRO
If you have ever looked up after decades of climbing and realized the ladder you have been on does not go where you thought it would, Natalie Benamou built HerCSuite for you. She is the founder and CEO of HerCSuite, a portfolio career network for women leaders in the second half of their careers. She has driven over $110 million in revenue as a business strategist and rainmaker. She is the CEO and president of HerHealthX, a nonprofit using agentic AI to bridge the care communication gap for women. And she hosts one of the top-ranked women's leadership podcasts, Women Leaders on the Move. In this conversation, Natalie and Erica compare notes on what the second half of a career actually looks like, what a portfolio career means in practice, how boards work and why women need to stop waiting to be tapped, and what AI is doing to the opportunity landscape for senior women right now.
INSIDE THE EPISODE
- The Titanic Moment. March 2020. Natalie was leading a division in trade shows - hundreds of events on a giant whiteboard - when everything stopped. She was the conductor keeping everyone playing while the ship was going down. By October of that year she knew it was time to fly through the open window. HerCSuite was born from that moment and the Zoom calls with girlfriends that followed.
- Multi-Hyphenate Is the New Career Path. Women in the second half of their careers are not looking for one next thing. They are building portfolio careers - board roles, entrepreneurship, advisory work, thought leadership, all at once. Natalie's Love/Like/Capable framework helps women figure out what they actually want to spend their time on before they jump into anything new.
- Women Don't Have the Luxury of Happy Hours. Erica on the networking gap: women are not building the informal connections that men build over drinks and dinners after work because they are home running households. The connections that get women into rooms and onto boards are the ones that have to be built deliberately - and that is exactly why communities like HerCSuite and HER Collective exist.
- The S&P Board Numbers Went Backwards. Women on S&P boards went from 38% to 25%. That is not progress, that is a reversal. Natalie's response: you gotta open your own doors. Board seats are the highest, hardest position in any company, and nobody is going to tap you on the shoulder. You have to build the visibility, the strategic narrative, and the relationships that get you there.
- CoLab3: The 90-Day Sprint That Builds Revenue and Community at the Same Time. HerCSuite's CoLab3 matches three members into 90-day sprint pods to solve a problem together and generate collaborative revenue. The first cohort built everything from an M&A assessment tool to a cybersecurity business checklist to an AI readiness survey. The model is built on the idea that the right three people in a room for 90 days can generate what none of them could alone.
- Skipping the AI Fundamentals. Erica on the AI gap she keeps seeing: people want to jump straight to autonomous AI workflows without learning how to actually communicate with the machine. It is like skipping vocabulary and grammar and trying to write a novel. The women who will close the AI gap are the ones who do the foundational work first.
- Identify Your Values Before Your Next Move. Natalie's most practical advice: before you make any next career move, know what matters most to you. Family, freedom, title, impact - whatever it is, get clear on it first, because every decision you make will either align with it or cost you something. The women who skip this step are the ones who land in the next chapter and realize it does not fit.
RESOURCES & LINKS
- HerCSuite Network: https://hercsuite.com/
- HerCSuite Membership: https://hercsuite.com/hercsuite-network-where-women-lead-the-future/
- Board Ready Summit: https://hercsuite.com/board-ready-summit/
- Women Leaders on the Move Podcast: https://hercsuite.com/podcast/
- Natalie Benamou on LinkedIn: https://www.linkedin.com/in/nataliebenamou/
ERICA'S RESOURCES & LINKS
Start small with me inside HER Jumpstart:
🤖 Grab your copy of THE AI GAP: https://amzn.to/3OAXAdL
📚 Get my first book, Glass Ceilings and Sticky Floors: https://amzn.to/4uvjbE5
💼 Follow me on LinkedIn: https://www.linkedin.com/in/ericarooney/
📸 Follow me on Instagram: https://www.instagram.com/ericaandersonrooney/
🎵 Check out my TikTok: https://www.tiktok.com/@ericaandersonrooney
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