Trust & Will scales compassionate customer support with their AI agent
facing the challenges of a high-stakes industry
Estate planning is an emotionally charged task where people must make deeply personal, life-defining decisions. For Trust & Will, providing clarity, empathy, and accuracy wasn’t just important—it was mission-critical.
“Our customers aren’t just asking, ‘What’s my account balance?’” explained Sophie Heller, Head of Member Support. “They’re navigating life-altering decisions about their estate plans—decisions that demand empathy, trust, and expertise in every interaction.”
Trust & Will’s initial scripted chatbot offered basic support, but was not able to handle the nuanced situations that our members contact our support team about every day. “Many of our members really struggled with the old bot,” Heller added. “In addition to the classic looping experience people encounter with a scripted bot, it also lacked the empathy required for the types of questions on our members’ minds.”
With a lean team managing growing demand, the limitations of the scripted approach became increasingly evident. Trust & Will needed a solution capable of blending scalable support with the human touch their customers valued most.
introducing Will-E, the AI agent
Recognizing the need for a more skilled AI solution, Trust & Will partnered with ada to launch an AI agent they affectionately named Will-E. Unlike its predecessor, Will-E leverages generative AI and the best artificial intelligence models to provide scalable, automated resolutions that combine efficiency with the quality of human-like interactions.
"Our customers are making some of the most important decisions of their lives, and Will-E has helped us deliver the empathy and clarity they need."
To ensure that generated responses are always safe, accurate, and relevant, the AI agent is designed to only pull information from company content. This is especially important in highly regulated industries such as legal tech.
Trust & Will wanted Will-E to be properly equipped with the content it needs to successfully service customers, so they invested in overhauling their knowledge base. The team thoroughly audited and revamped their knowledge base, closing content gaps and collaborating closely with ada experts to optimize performance.
“We knew Will-E could only be as good as the information we provided,” said Heller. “The transformation was night and day. Instead of outdated or incomplete data, we gave Will-E the tools to succeed right out of the gate.”
"One of the biggest selling points of Will-E has been how human it feels. We’ve literally had to remind members that they weren’t speaking with a real person. That kind of feedback validates everything we aimed to achieve. Will-E has been a game-changer, significantly reducing escalations and making a huge difference in improving the customer experience while lightening our team’s workload."
transformative results for customers and teams
Will-E’s introduction marked a turning point for Trust & Will’s service operations. By covering routine inquiries, Will-E empowered the team to focus on high-stakes, emotionally charged cases. "We’ve gone from firefighting to delivering white-glove service. Will-E doesn’t just handle inquiries, it gives us the bandwidth to be there for our customers when they need us most,” said Heller.
"Our AI Agent, Will-E has transformed how we approach customer support. By handling inquiries, it’s freed our team to focus on high-value, white-glove interactions. It’s not just about efficiency; it’s about giving our team the bandwidth to provide empathetic support for complex, nuanced questions."
Will-E’s conversational fluency also tackled persistent customer frustrations. For example, many of our users frequently struggle with applying promotional codes to their purchases. The old chatbot couldn’t work out how to help them, which resulted in conversations having to be escalated to human agents. “Will-E would simply say, ‘Don’t forget to hit the apply button,’ and that small guidance eliminated so much confusion,” said Ashley Tridle, Support Supervisor. “It’s those little, thoughtful interventions that reduce noise for our team while creating a seamless experience for our customers.”
This shift has been a game changer for their customers and team alike.
"Like most support teams, our team works hard to provide uninterrupted coverage during major holidays when the rest of the company is OOO. This past Thanksgiving, though, I was delighted to offer the team a fully dark 4 day weekend, knowing that Will-E was there to keep our operations running smoothly. It's been huge for morale to allow the team extended time over the holidays to recharge outside the support queues."
enhancing the AI Agent through coaching
The key to Will-E’s ongoing success? Using ada’s advanced coaching tools to continuously improve is performance. The Trust & Will support team treated Will-E like a new team member, dedicating significant time to its training and continuous improvement.
By doing this, Trust & Will could refine its responses to stay aligned with evolving customer needs.
"Coaching Will-E is like training a new employee—but faster and more consistent. By aligning the AI Agent with updated FAQs and real-time insights, we’ve created a self-improving system that delivers personalized support to our customers at scale."
This iterative process allowed Trust & Will to identify knowledge gaps and make targeted improvements, ensuring Will-E stayed responsive and effective. Coaching also surfaced actionable data, helping prioritize resources for the greatest impact.
metrics that matter
Trust & Will’s collaboration with ada has reshaped customer support with measurable success.
“Our metrics give a clear picture of how much value Will-E contributes to our support experience,” Heller said. “Our live chat experience isn’t just about automating tasks – although that has been huge for my team – but we also are able to deliver a conversational experience that maintains a high standard of trust and empathy for our members.”
“In less than a year, Will-E has grown and maintained a steady 70% automated resolution rate,” Heller added. "It's been a major factor in allowing us to offer world-class support from a small but mighty in-house team.”
looking to the future
With Will-E’s success, Trust & Will is exploring new ways to scale their impact. While maintaining our 70% automated resolution rate remains a priority, we’re also excited to explore what’s next. There’s so much potential with ada to streamline backend workflows,” said Sophie Heller, Head of Member Support. “
Trust & Will sees Will-E as more than an automation tool—it’s a critical partner driving their journey toward sustainable growth and profitability. “With ada, we’ve found a scalable solution that aligns with our values,” Heller concluded. “We’re excited to see how Will-E evolves alongside us.”
Interested in learning more about Trust & Will's journey? Watch their webinar on how to interview AI agents for customer service .