#StartupsEverywhere: Chicago, ill.
#StartupsEverywhere: Jay Wilburn, Founder & CEO, BestFarewell
This profile is part of #StartupsEverywhere, an ongoing series highlighting startup leaders in ecosystems across the country. This interview has been edited for length, content, and clarity.
Simplifying the Logistics of Loss
BestFarewell is a Chicago-based AI-powered platform that helps families navigate the complex logistics of estate planning and bereavement. We sat down with founder Jay Wilburn to discuss the development of his proprietary SageLink AI, the administrative burden on remote startups, modernized bereavement treatment, and the regulatory hurdles surrounding electronic wills.
Tell us about your background. What led you to BestFarewell?
BestFarewell was inspired by my family's experience after losing our grandfather. His passing left us scrambling to uncover his affairs—a situation that made me realize how unprepared families can be.
I realized there was a desperate need for a tool that helps families align before a loss occurs. With 16 years of experience as a software engineer, I extensively researched the space, talking to funeral directors and families to understand where the systems break down. I’ve spent my career as the "bridesmaid" in various startups. This experience pushed me to finally become the "bride," and to build a solution that ensures families have everything they need before they actually need it.
What is the work you all are doing at BestFarewell?
We provide an AI-powered bereavement support system for family and estate management. It begins with the Family Management System, aka "Family CRM", to centralize documents and information, but it expands into active support during a loss. Users can generate AI obituaries, build dedicated memorial pages, and use our estate planning tools to create readouts for financial advisors.
While our users are families, our business model is business-to-business-to-consumer (B2B2C). We partner with financial advisors and grief counselors, but our primary focus is the employer benefit side. Research shows that an overwhelming majority of employees want a bereavement benefit, yet most companies lack one. We’re also seeing a significant trend of new parents signing up; the moment you have a child, your perspective on mortality and family security changes entirely.
Can you tell me more about the technology you use at BestFarewell and how it enhances the experience?
I built a proprietary AI layer, SageLink, on top of OpenAI and Claude Opus. We did this for security and empathy. For privacy, we ensure family data isn't shared with public models, and we train Sage Link to understand the art of the memory.
Baseline AI models lack the sensitivity required for these moments. Our model is trained on 10,000 memorials and research from funeral directors, so it understands compassion. If the system knows that Aunt Rose was famous for her apple pies, Sage Link will automatically include those details in her obituary. Turning a six-hour, high-stress writing task into a four-minute process gives families the time they need to grieve and support one another.
What is your experience navigating data privacy frameworks?
Data privacy and security are really important because you're dealing with people's personal information, memories, and livelihoods, and it's important to build and maintain customers' trust.
This started before we even launched, speaking with experts to make sure we had everything in place. In order to become fully compliant and certified takes a long time and a lot of money. Part of what we are raising money for is to maintain SOC type II compliance, which is expensive but necessary.
Are there any local, state, or federal startup issues that you think should receive more attention from policymakers?
Policymakers should consider the administrative burden on small, remote-first companies. Navigating different state regulations for things like unemployment insurance or notarization is a massive resource drain. For a solo founder, spending 40 hours on out-of-state paperwork takes time away from innovation.
The most significant barrier for this space broadly is the lack of national uniformity regarding electronic or "e-wills." While the digital age has made many things easier, the U.S. government does not yet recognize electronic wills nationwide. It’s a state-by-state patchwork. This limits our ability to provide a seamless, end-to-end legal experience. If e-wills were standardized, we could partner with more firms to allow users to execute legal documents directly through our platform.
Additionally, I’d love to see policies that encourage companies to treat bereavement as more than just a few days of leave. It often takes weeks for an employee to truly recover from the logistical and emotional weight of a loss. Policies that incentivize companies to provide planning tools would help the 2.8 million families dealing with death every year.
What are your goals for BestFarewell moving forward?
I’m a one-man band raising a $1M pre-seed round to hire and scale our engineering and marketing. My goal is to get into as many company open-enrollment windows as possible. In five years, I want BestFarewell to be a standard bereavement benefit offered by at least 100,000 companies across every state. This isn’t a quick exit play for me; it’s a lifetime company. Death is inevitable, and the generations after us deserve a modern, secure, and compassionate way to manage it. I want to build a safe space where families can focus on memories rather than paperwork.
All of the information in this profile was accurate at the date and time of publication.
Engine works to ensure that policymakers look for insight from the startup ecosystem when they are considering programs and legislation that affect entrepreneurs. Together, our voice is louder and more effective. Many of our lawmakers do not have first-hand experience with the country's thriving startup ecosystem, so it’s our job to amplify that perspective. To nominate a person, company, or organization to be featured in our #StartupsEverywhere series, email advocacy@engine.is.
