Elizabeth Fierman

The most expensive mistakes in my life didn't begin as crises. They began as conversations I didn't want to have. A conversation with an employee who wasn't the right fit. A conversation with a peer when trust started to erode. A conversation with a customer whose expectations were changing. And sometimes, the hardest conversation of all was the one I needed to have with myself. At the time, avoiding those conversations felt reasonable. I told myself I needed more information, better timing, or the right words. Looking back, I realize I wasn't waiting for any of those things. I was avoiding discomfort. The problem is that reality doesn't wait. Relationships drift, trust erodes, small issues become big ones, and opportunities quietly disappear. The conversations we avoid don't go away, they compound. Like interest on a debt. The longer we wait, the more emotional and expensive they become. One of the biggest leadership lessons I've learned is that difficult conversations rarely get easier with time. They almost always become harder. Today, when I catch myself hesitating, I ask one simple question: What conversation am I avoiding? More often than not, I already know the answer. The challenge isn't finding the right words. It's finding the courage to stop waiting. #leadership #FutureOfWorkWork #learningrning #growthmindsetet #humancapitalmanagement #presenceunderpressure

If your team runs on Google, this one's for you! Robin is now live on Google Cloud Marketplace, which means you can apply your existing Google Cloud commitment directly to your Robin purchase. Got Google Cloud credits and a workplace that needs fixing? This is about as easy as it gets. More details here: https://lnkd.in/gmuskPVM

For most of my career, I've been collecting lessons. Over the past few years, I finally decided to write them down. After more than 25 years in leadership, one IPO, multiple company exits, incredible successes, painful failures, and some of the hardest moments of my life, one belief kept surfacing. Leadership isn't about having all the answers. It's about how you show up when no one has them. 9/11 taught me that, the financial crisis reinforced it and COVID proved it again. Some of life's hardest personal moments made me truly understand it. Technology will continue to change. Markets will continue to change. Business models will continue to change. The leaders who thrive won't be the ones who predict every change correctly. They'll be the ones who remain grounded, tell the truth, adapt quickly, and help others move through uncertainty. This idea became a book, Presence Under Pressure, releasing in the next couple months. Over the next few weeks, I'll share some of the lessons that helped shape it. I hope they resonate with those of you leading through uncertainty today. #Leadership #LeadershipDevelopment #HumanCapital #Growth #PresenceUnderPressure 

Today, I'm honored to share that I've been named to the Boston Globe Media 2026 Tech Power Players list, recognizing 50 of the most influential and interesting leaders shaping technology across New England—a recognition that also reflects the work being done through AI-Powered Women and the extraordinary ecosystem helping bring it to life. What began as a conference at MIT last year has rapidly grown into a global learning platform for workforce readiness and human-centered AI leadership. We've brought together technologists, psychologists, anthropologists, philosophers, neuroscientists, artists, mindfulness practitioners, founders, researchers, and enterprise leaders to wrestle with a question that feels increasingly urgent: How do we ensure increasingly intelligent systems are guided by conscious, responsible, deeply human leadership? The question that keeps me up at night isn't whether AI will become more intelligent. It's whether humans will. Organizations are investing billions in AI while underinvesting in the human systems required to realize its value: leadership, workforce readiness, governance, culture, trust, and change management. Far fewer are asking the harder question: What kind of humans, leaders, organizations, and societies must we become as these technologies grow more powerful? That is the work of AI-Powered Women. Women are often closest to the human consequences of these systems—through leadership, governance, education, ethics, communication, caregiving, and organizational culture—yet remain underrepresented in many of the technical, capital, and executive decisions shaping AI's trajectory. But that gap is not just about women and diversity. It's a leadership, workforce, and innovation issue. We're building the leadership capacity, technical fluency, research, frameworks, networks, and economic opportunities that enable women not just to adapt to the future of AI, but to help shape it. THANK YOU to Boston Globe Media for recognizing this work, and to our global network of ambassadors, speakers, partners, researchers, educators, sponsors, and thousands of women around the world who have contributed their voices, wisdom, and leadership to this growing movement. Full list of the 2026 Tech Power Players: https://lnkd.in/eNWxtm-9 __________________________________________________________ For those who feel called to engage, there are three pathways into this work: 1) Attend our conference at MIT this September: https://lnkd.in/emnuiYTd 2) Get Your Organization Involved: https://lnkd.in/eERC-Kmx 3) Invest & Partner: help scale our platform as an investor, sponsor, or ambassador, visit https://lnkd.in/eHbThAdD to learn more.

After 3.5 years, I’m officially closing an unforgettable chapter as VP of Marketing at Repsly. This experience gave me far more than career growth — it was a true career highlight. I had the opportunity to lead teams across marketing and business development, build meaningful work, take creative risks, keep learning, and accomplish more than I thought possible. To my team: I’m deeply grateful for your talent, trust, and constant collaboration. You made the hard work fun and the wins even more rewarding. We climbed mountains together — literally and figuratively ☺️⛰️ To the leaders and colleagues who supported me, thank you for always believing in me. To Jeff Lord, CPA, and to my parents (who won’t see this), nothing I accomplish happens without your constant support 🫶 I’m leaving with a full heart, immense pride in what we built together, and real excitement for what’s next. But before that starts, I owe a couple kids a day off from school to eat donuts, draw unicorns, and play soccer. ✨

When I was going through my own career transition, so many people in my network showed up for me. Conversations, perspective, introductions. It made a bigger difference than I can really put into words. Two months into my role as Director of Selection at Northwestern Mutual, and I’ve been thinking a lot about how to pay that forward. So consider this me doing my part now. Think of me as your unofficial career coach who happens to have a few unique opportunities to share. If this sounds even a little familiar... You’re a mid to senior level professional who has built a solid career but feels that nudge that there might be something more out there. I’d love to connect. I remember how real that feeling can be. It can also feel like you’ve invested too much to pivot. But what I’ve seen in just two months here is how powerful it can be when experienced professionals channel their skills, networks, and drive into something more entrepreneurial. I’m selectively bringing on a few career changers into our Lakewood office as financial advisors. The people who tend to thrive are relationship driven, self-motivated, and excited by the idea of building something of their own. The long term draw is pretty simple: impact, independence, and income. I’m lucky to do this alongside an incredible network of talented people, many of whom have made this same leap themselves. If any of those feelings sound familiar, I’m always happy to have a confidential, low pressure, exploratory conversation. And if someone came to mind while reading this, I’d really appreciate the introduction.

We just updated Robin's mark. It's the second time we've meaningfully reworked the brand, but it's the first time that it's actually felt like us.