Voice
Gaby
0:00/1:34
Gaby is BetterSure’s AI agent who began by booking complimentary will consultations for every client and has since evolved to draft complete wills end-to-end through natural conversation.
Year :
2025
Industry :
Insurance
Client :
Bettersure
Project Duration :
6 weeks
Background:
BetterSure approached us with a clear and pressing need: how to better activate their existing client base and deliver meaningful value after the initial sale. For many customers, buying a home and taking out insurance is a milestone moment — but one important step was often left incomplete: putting a will in place. Although BetterSure included a complimentary will consultation as part of their policies, uptake remained low. This created a missed opportunity both for clients, who lacked an essential safeguard, and for BetterSure, who wanted to reinforce their role as a trusted, full-service provider.
Our Task :
To address this gap, we launched Gaby, the very first AI agent developed by Nineteen58. Her role was designed to bridge the follow-through gap and ensure clients made use of the service already available to them. Specifically, Gaby was tasked to:
Call and engage the entire client base in natural, conversational interactions.
Congratulate new homeowners on their milestone and remind them of the importance of having a will in place.
Clearly explain that a complimentary consultation was included with their policy, removing any uncertainty around additional cost.
Seamlessly book a consultation with a human advisor by identifying a suitable time and syncing directly into the advisors’ calendars.
Challenge :
The scale of the outreach posed the primary challenge. To manually contact every customer, congratulate them, explain the service, and then secure a booking would have required a substantial and costly human workforce. Even then, consistency in messaging and follow-through would have been difficult to achieve. Gaby solved this challenge by:
Engaging the entire client base in a short period of time, something not feasible with human agents alone.
Proactively handling the booking process, which significantly reduced friction and improved customer follow-through.
Creating a customer experience that felt simple and natural: no lengthy forms, no waiting on hold, just a quick interaction that resulted in a confirmed appointment.
Evolution :
While Gaby’s initial role was to activate existing clients and secure bookings for consultations, her capabilities quickly grew as both the client and the technology matured. Over time, she expanded beyond scheduling into the full drafting of wills, collecting all necessary details through conversation and generating completed documents. This marked a major evolution in her function:
From a booking assistant that handed off to humans, she became a specialist AI legal assistant capable of delivering the service herself.
This progression demonstrated the adaptability of AI agents — starting with a narrowly defined task and scaling up to deliver full service at enterprise quality.
For BetterSure, this meant not only improved engagement but also tangible operational efficiency, with more clients completing wills without requiring the same level of manual intervention.
More Agents
Voice
Gaby
0:00/1:34
Gaby is BetterSure’s AI agent who began by booking complimentary will consultations for every client and has since evolved to draft complete wills end-to-end through natural conversation.
Year :
2025
Industry :
Insurance
Client :
Bettersure
Project Duration :
6 weeks
Background:
BetterSure approached us with a clear and pressing need: how to better activate their existing client base and deliver meaningful value after the initial sale. For many customers, buying a home and taking out insurance is a milestone moment — but one important step was often left incomplete: putting a will in place. Although BetterSure included a complimentary will consultation as part of their policies, uptake remained low. This created a missed opportunity both for clients, who lacked an essential safeguard, and for BetterSure, who wanted to reinforce their role as a trusted, full-service provider.
Our Task :
To address this gap, we launched Gaby, the very first AI agent developed by Nineteen58. Her role was designed to bridge the follow-through gap and ensure clients made use of the service already available to them. Specifically, Gaby was tasked to:
Call and engage the entire client base in natural, conversational interactions.
Congratulate new homeowners on their milestone and remind them of the importance of having a will in place.
Clearly explain that a complimentary consultation was included with their policy, removing any uncertainty around additional cost.
Seamlessly book a consultation with a human advisor by identifying a suitable time and syncing directly into the advisors’ calendars.
Challenge :
The scale of the outreach posed the primary challenge. To manually contact every customer, congratulate them, explain the service, and then secure a booking would have required a substantial and costly human workforce. Even then, consistency in messaging and follow-through would have been difficult to achieve. Gaby solved this challenge by:
Engaging the entire client base in a short period of time, something not feasible with human agents alone.
Proactively handling the booking process, which significantly reduced friction and improved customer follow-through.
Creating a customer experience that felt simple and natural: no lengthy forms, no waiting on hold, just a quick interaction that resulted in a confirmed appointment.
Evolution :
While Gaby’s initial role was to activate existing clients and secure bookings for consultations, her capabilities quickly grew as both the client and the technology matured. Over time, she expanded beyond scheduling into the full drafting of wills, collecting all necessary details through conversation and generating completed documents. This marked a major evolution in her function:
From a booking assistant that handed off to humans, she became a specialist AI legal assistant capable of delivering the service herself.
This progression demonstrated the adaptability of AI agents — starting with a narrowly defined task and scaling up to deliver full service at enterprise quality.
For BetterSure, this meant not only improved engagement but also tangible operational efficiency, with more clients completing wills without requiring the same level of manual intervention.
More Agents
Voice
Gaby
0:00/1:34
Gaby is BetterSure’s AI agent who began by booking complimentary will consultations for every client and has since evolved to draft complete wills end-to-end through natural conversation.
Year :
2025
Industry :
Insurance
Client :
Bettersure
Project Duration :
6 weeks
Background:
BetterSure approached us with a clear and pressing need: how to better activate their existing client base and deliver meaningful value after the initial sale. For many customers, buying a home and taking out insurance is a milestone moment — but one important step was often left incomplete: putting a will in place. Although BetterSure included a complimentary will consultation as part of their policies, uptake remained low. This created a missed opportunity both for clients, who lacked an essential safeguard, and for BetterSure, who wanted to reinforce their role as a trusted, full-service provider.
Our Task :
To address this gap, we launched Gaby, the very first AI agent developed by Nineteen58. Her role was designed to bridge the follow-through gap and ensure clients made use of the service already available to them. Specifically, Gaby was tasked to:
Call and engage the entire client base in natural, conversational interactions.
Congratulate new homeowners on their milestone and remind them of the importance of having a will in place.
Clearly explain that a complimentary consultation was included with their policy, removing any uncertainty around additional cost.
Seamlessly book a consultation with a human advisor by identifying a suitable time and syncing directly into the advisors’ calendars.
Challenge :
The scale of the outreach posed the primary challenge. To manually contact every customer, congratulate them, explain the service, and then secure a booking would have required a substantial and costly human workforce. Even then, consistency in messaging and follow-through would have been difficult to achieve. Gaby solved this challenge by:
Engaging the entire client base in a short period of time, something not feasible with human agents alone.
Proactively handling the booking process, which significantly reduced friction and improved customer follow-through.
Creating a customer experience that felt simple and natural: no lengthy forms, no waiting on hold, just a quick interaction that resulted in a confirmed appointment.
Evolution :
While Gaby’s initial role was to activate existing clients and secure bookings for consultations, her capabilities quickly grew as both the client and the technology matured. Over time, she expanded beyond scheduling into the full drafting of wills, collecting all necessary details through conversation and generating completed documents. This marked a major evolution in her function:
From a booking assistant that handed off to humans, she became a specialist AI legal assistant capable of delivering the service herself.
This progression demonstrated the adaptability of AI agents — starting with a narrowly defined task and scaling up to deliver full service at enterprise quality.
For BetterSure, this meant not only improved engagement but also tangible operational efficiency, with more clients completing wills without requiring the same level of manual intervention.