Seven Cities, Eight Weeks, and Why I Spent Fall 2025 Living Out of a Suitcase

The Method Behind the Conference Marathon

You know that moment when you realize you've been building something in a vacuum? That was me, eighteen months ago, sitting in our Montreal office, designing features for trust officers based on assumptions rather than observation. Sure, we had user interviews. We ran focus groups. We analyzed workflows until our eyes crossed. But there's something fundamentally different about being present where the work actually happens.

So this fall, I did what any rational CEO would do: I became a conference nomad. Seven cities. Eight weeks. More hotel coffee than any human should consume. From Fort Lauderdale's September humidity to Delaware's October chill, I planted myself at every major trust conference that would have me.

Why? Because software that actually works doesn't come from assumptions, it comes from understanding the reality of trust administration, not the theory.

The Geography of Trust Administration

The roadshow covered more ground than a traveling circus:

• Fort Lauderdale, FL - Florida Trust Conference in the retirement capital of America
• Portsmouth, NH - The Tri-State Trust Forum, where New England pragmatism meets fiduciary excellence
• Hershey, PA - Yes, Chocolatetown. The Pennsylvania Wealth Management & Trust Conference between the pumpkin decorations
• Nashville, TN - Tennessee Trust & Wealth Management Conference, complete with genuine southern hospitality
• Vestavia, AL - Alabama's Annual Trust & Wealth Management Symposium, intimate and insightful
• Wilmington, DE - Delaware Bankers' Association Trust Conference in the trust capital of America
• Toronto, ON - Risk Mitigation in Estate Planning and Administration, *more legal and estate admin but a flight was taken to be able to speak to professionals in person!

What the Conference Circuit Revealed

The presentations ranged from cryptocurrency estates to multi-generational wealth transfer strategies. Session after session revealed the complexity trust officers navigate daily, they're part therapist, part detective, part accountant, and somehow expected to excel at all three simultaneously.

The pattern became clear after the third conference: similar challenges, different scales. Florida sessions focused on volume and efficiency. Delaware discussions centered on navigating intricate trust structures. Tennessee presentations addressed multi-generational family business transitions. Each region brings its own flavor to the same fundamental challenges.

But what came through clearly was the palpable dedication in every session, every panel discussion, every networking break. These professionals aren't just processing paperwork. They're guardians of legacies, shepherds of family wealth, and often the steady hand during life's most difficult transitions.

The Education Between Sessions

Conference sessions taught the theory, but the exhibit halls and networking breaks revealed the reality. Watching demonstrations of current software "solutions," hearing the questions trust officers asked vendors, observing what sparked genuine interest versus polite nodding, these moments were invaluable.

The disconnect was obvious: most software treats trust administration like it's still 1995. The creative workarounds I heard about, spreadsheet systems, manual processes, duplicate data entry, aren't signs of resistance to technology. They're evidence that the technology hasn't caught up to the profession's needs.

Building From Reality, Not Assumptions

Being present at these conferences, not just as a vendor but as an active participant and observer, changed our entire approach. Attending sessions on trust accounting reform, regulatory updates, and emerging challenges provided context that no user interview could capture.

The questions trust officers ask, the problems they discuss over coffee, the solutions they've cobbled together, these insights can't be gathered from a distance. They require presence, patience, and genuine interest in understanding the profession beyond surface-level pain points.

What Happens Next

Seven cities taught me that trust administration isn't broken, it's been underserved by technology. The sophistication of modern trust work, the complexity of regulations, the nuance of family dynamics, all of this deserves software built by people who understand the depth of the profession.

Every mile traveled, every session attended, every booth conversation it all pointed to the same conclusion: the trust industry doesn't need another software vendor making assumptions. It needs partners who invest the time to understand that behind every estate is a family, behind every trust is a story, and behind every screen is a professional managing incredible complexity with insufficient tools.

The Future We're Building

Here's what became crystal clear across every conference: the future of trust administration isn't about replacing trust officers it's about amplifying their expertise. The complexity I witnessed isn't going away. Digital assets, international real estate, multi-generational planning, evolving tax landscapes - these challenges will only intensify.

But imagine this: What if your software actually learned from your workflows instead of forcing you into rigid processes? What if it could recognize that a QTIP trust requires different documentation than a special needs trust, and automatically adjusted its requirements? What if new team members could learn your firm's specific approaches through intelligent, in-platform training that adapts to their experience level?

This isn't science fiction. It's what happens when you combine genuine understanding of trust administration with thoughtful application of automation and AI. Not AI that tries to replace judgment, but AI that eliminates the mundane - the duplicate data entry, the manual calculations, the document hunting. AI that recognizes patterns in your work and suggests efficiencies you hadn't considered.

Think about it: every trust officer I met has developed their own system of workarounds. They've created brilliant solutions to software limitations. What if we could learn from all of these solutions collectively? What if your software could configure itself based on whether you're managing a simple revocable trust or a complex generation-skipping trust? What if it could train your junior staff not just on generic trust administration, but on your specific firm's best practices?

The future of trust administration is collaborative intelligence, human expertise enhanced by technology that actually understands the work. It's about building entire trust teams that can scale their impact without sacrificing the personal touch that makes this profession essential.

Our Commitment

The suitcase is unpacked (finally), but the engagement continues. Because building software for trust professionals isn't a conference booth exercise, it's an ongoing commitment to understanding and serving the people who make this industry work.

We're not just building features based on what we heard this fall. We're building a platform that continues to listen, learn, and evolve with the profession. Every workflow, every edge case, every creative solution you've developed, these aren't problems to be standardized away. They're insights to be understood and intelligently supported.

To everyone who stopped by our booth, attended the same sessions, or shared their perspectives: thank you. You're why Estateably exists, and you're why this fall's roadshow was just the beginning.

Stay tuned: More ABA Trust School Lessons will be posted before year-end, continuing our series that uses analogies to demystify complex trust administration concepts.