Hi, I’m Jill Mastroianni.

When I speak, people lean in—ready to rethink death, planning, and the legacy they’ll leave behind. For more than a decade, I practiced as a trusts and estates attorney, guiding families through grief, decision-making, and the overwhelming logistics that come with death. Now, I bring that experience to stages, workshops, and conversations that matter—offering audiences a new way to think about death, life, and how to prepare for both.

I don’t just show up to speak—I show up to partner. Every talk is thoughtfully customized to meet the goals of your event and the real lives of your audience.

If you’re looking for someone who can bring compassion, clarity, and a touch of lightness to the conversation around death, planning, and legacy—send me a message.

5 Reasons to Book Jill

  • Jill brings clarity, heart, and just the right amount of humor to a topic most people avoid. With a background in law, a gift for storytelling, and a deeply compassionate presence, her talks are disarming, deeply human, and genuinely transformative.

  • Death readiness doesn’t have to be overwhelming. Jill makes it approachable by offering simple steps, real-life examples, and tangible takeaways your audience can use right away to feel more prepared and at peace.

  • Whether she’s speaking to caregivers, professionals, community members, or families, Jill customizes every talk to meet the needs, fears, and hopes of your group—ensuring it resonates deeply and feels relevant.

  • Jill’s talks feel like a conversation with a wise friend. She doesn’t preach. She connects—with authenticity, humility, and insight that moves people to reflect, share, and take meaningful action.

  • From the first email to the final thank-you, Jill is collaborative, thoughtful, and easy to work with. She’s committed to making your event a success and creating a positive experience for both your team and your audience.

To find out more, send Jill a message.