45. Stop Pretending You Know Everything, with Alena DeSalvo, Sightly

The best leaders aren't the ones with all the answers, they're the ones willing to ask more questions. Alena DeSalvo didn't set out to work in media; she kind of stumbled into it. Now, as SVP and Head of Marketing at Sightly, she's figuring out leadership, growth, and what it means to build something in real time. This week, host Lauren Douglass sits down with Alena to talk about what's driving her right now; not the polished highlight reel, but the actual messy middle of building a career. They get into how her psychology background shapes the way she thinks about marketing and what she had to unlearn about being a young woman in business (hint: it involves exclamation points, high heels, and firm handshakes). Alena opens up about advocating for yourself when no one's going to tap you on the shoulder, why handwritten notes still matter more than AI transcripts, and her hot take on AI-generated copy that needs to stop. This is a conversation about asking more questions, leaning into what you don't know, and learning to let go of control. It's a great reminder that not every career path is planned - sometimes you just stumble into the right industry and build from there. If you're early in your career, still figuring out how you want to lead, or just trying to find your footing, this one's for you.