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Estate planning has traditionally been one of the most overlooked, avoided, and intimidating conversations between advisors and their clients. Yet, for many families, ensuring that a legacy is protected and transferred smoothly is just as critical as wealth building and investment strategy. At this year’s Future Proof Festival, Cody Barbo, Co-Founder and CEO of Trust & Will, shared how his company is reshaping the industry by bringing estate planning into the modern age—specifically through a new platform for advisors, EstateOS.
Launched in June 2025, EstateOS is the first intelligent estate planning platform built for professionals. With features like AI-driven document extraction, plan scoring, and secure client plan visibility, it is designed to help advisors initiate and maintain estate planning conversations that historically have been difficult to start, harder to manage, and even harder to keep updated. The goal: to empower advisors to create stronger, longer-lasting relationships with clients while providing essential services that protect families’ legacies.
A Vision Rooted in Personal Experience
For Barbo, the story of Trust & Will is deeply personal.
“We started this business for ourselves,” he explained. “My wife had lost her dad when we began dating, and their family went through probate—it was a total mess. At the time, I didn’t have the money to hire an attorney, and what was available online just wasn’t good. So with my co-founders Daniel and Brian, we built a more modern, affordable solution. Now, eight years later, we’ve helped over a million families with their estate plans.”
That core mission—to make estate planning accessible—soon evolved. In 2020, advisors began reaching out, asking if Trust & Will could provide tools for their clients. From those early conversations, Trust & Will designed its advisor platform, which now supports more than 20,000 advisors across RIA firms and large broker-dealers.
EstateOS: Building Confidence for Advisors
Advisors may know estate planning is essential, but many struggle with how to incorporate it into client discussions. Barbo has seen this challenge firsthand.
“Advisors would tell me, ‘I know my clients need this, but I don’t know how to bring it up.’ That’s why we built EstateOS. With our intelligent estate assistant, an advisor can input a client’s scenario—say they’ve moved states, had children, or bought a new property—and get expert-level answers in seconds. It prepares the advisor to walk confidently into that meeting and deliver value right away.”
The platform doesn’t just stop at conversation support. EstateOS introduces tools like Plan Strength, a system that ranks the health of an estate plan from red to green, much like a credit score. Advisors can also upload legacy PDF documents from clients’ older estate plans, with the system instantly generating a snapshot summary and surfacing planning opportunities.
For firms managing hundreds or thousands of households, these features create efficiency, uncover new assets, and reveal opportunities that advisors might have otherwise missed, strengthening both compliance and long-term planning quality.
Empowering Families, Simplifying Complexity
Estate planning carries emotional weight. Families often avoid the topic until it becomes urgent, creating added stress for both clients and advisors. EstateOS is designed not only to streamline the creation and updating of documents but also to help families stay connected through visibility and secure sharing features.
One unique feature is legacy contacts, which allow clients to proactively share their estate plan with family members and revoke access as needed. Barbo relates this directly to his own experience:
“When we started the company, my parents had never mentioned their estate plan to my brother or me. I didn’t know where it was or even if their attorney was still practicing. Now, in my own plan, my wife and my mom have direct access. If something happens, they can log in and have everything they need. That’s the kind of peace of mind we want advisors to deliver to their clients.”
This approach streamlines not just planning but also transitions. Having acquired a probate company, Trust & Will has already supported more than 4,000 settlements. Knowing that the documents hold up in court—and ease what can be one of the most difficult times for families—reinforces the platform’s credibility.
Scaling Insights for Firms and Institutions
For larger enterprises, EstateOS translates into robust data and actionable insights. Trust & Will partners with firms like Fifth Third Bank, Northwestern Mutual, and LPL Financial to surface new opportunities for client engagement and asset discovery.
Barbo offered an example: “Fifth Third Bank launched a free will offer for its four million clients last quarter. Tens of thousands took advantage. Many upgraded to a trust—which means they have assets and planning needs. That’s a huge discovery opportunity for the bank’s advisors and planners, and we can provide reporting that helps deepen those relationships at scale.”
By leveraging aggregated data, firms gain new visibility into coverage gaps, tax planning needs, and even insurance opportunities—all while enhancing client trust through a seamless, advisor-led experience.
The Future of Intelligent Estate Planning
Looking ahead, Barbo sees Trust & Will’s growth trajectory tied directly to the needs of advisors and their clients. Future developments include a life events engine, designed to proactively anticipate when a plan may need updating (marriages, moves, new children), and expanded tools for related stakeholders, including estate attorneys and planned giving professionals.
“My dream,” Barbo said, “is that estate planning becomes more of a behind-the-scenes process. People can live their lives, and advisors—armed with platforms like EstateOS—will know when to step in and guide them. Estate planning doesn’t need to be something people dread or only touch every few decades. With technology, it can be intuitive, proactive, and always up to date.”
Trust & Will’s mission remains consistent: to help families protect their legacy. But as EstateOS continues to develop, it also sharpens the advisor’s toolkit, equipping professionals with the structure, clarity, and guidance they need to make estate planning a natural extension of wealth management.
Why This Matters to Advisors
For financial advisors, building relevance in an increasingly commoditized investment landscape requires going deeper into the aspects of planning that truly matter to families. Estate planning is one of those areas. With EstateOS, advisors not only have a simplified path to addressing client needs but can also establish themselves as the trusted partner guiding families through life’s most important transitions.
As Barbo put it: “Even with all of the technology we’ve built, our proudest success metric is still getting clients to complete their plans. Advisors have incredible relationship equity with families, and when we give them the tools to turn those conversations into action, everyone wins.”
Lesrn more about Trust & Will by visiting their website here.
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