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By deploying Lisa, their Observe.AI VoiceAI Agent, Boundless Learning engages prospective learners at scale, helps individuals take the next step on the right education and career path, and connects qualified students to human advisors without adding operational burden.
Boundless Learning partners with universities to support student acquisition, enrollment, and retention. A core part of that mission is ensuring that prospective learners who have expressed interest in continuing their education have a clear, timely path to speak with an advisor and understand their options.
Over time, the team saw a gap emerge between learner intent and learner experience. Learners showed interest but did not always move forward at the right moment. Advisors were forced to balance serving active prospects with repetitive outreach that delivered diminishing returns. This created both a learner experience gap and growing pressure on advisor capacity.
“When considering the large volume of prospective learners who had raised their hand at some point, we wanted to think about how we could create more opportunities for meaningful connection,” says Chris Martin, Enrollment Operations Manager at Boundless Learning.
The challenge was not a lack of demand. It was a scale. Advisors are most impactful when they have high-quality conversations about goals, programs, and next steps. But reaching large populations of prospective learners consistently and quickly had become increasingly difficult to do with human outreach alone.
Boundless Learning approached AI outreach as a way to extend access and continuity of engagement, not replace the human connection at the center of the learner experience.
“We wanted to think about how AI could best serve us in populations where we’ve got really high volume of contacts we want to reach out to,” says Lucy Lomas, Director of Learner Experience Enablement at Boundless Learning. “And we wanted to think about how that connects to our human staff.”
Lisa, Boundless Learning’s AI Agent, was designed to engage prospects early, understand intent, and guide learners to the right next step. For some, that meant booking time with an advisor. For others, it meant transferring the conversation to a human in the moment so they could dive into program options, career goals, or enrollment requirements.
“When we look at the opportunities presented by AI, we led with, ‘How can AI best support our biggest value, which is our people,’” says Martin. “AI can help us create more opportunities for connection and then get learners to the experts when it matters.”
“AI can help us create more opportunities for connection and then get learners to the experts when it matters.”
- Chris Martin, Enrollment Operations Manager, Acquisition & Retention
As a result of deploying a proactive outbound Voice AI agent, advisors were not just freed up. Their role became more strategic and more human, with more time for complex, emotional, or high-stakes conversations. Lisa focused on connecting with prospective students, and advisors focused on what those students needed in their learning journey.
Because Boundless Learning operates across multiple university partners, outbound communication is subject to strict compliance requirements. Every interaction must include recorded line statements, transparency about Boundless Learning’s role, and disclosure when the caller is an AI assistant.
“Compliance was the first thing we focused on,” says Crystal Michaelson, Quality Improvement Manager at Boundless Learning. “We needed to make sure the AI was following the same rules our human agents follow.”
Lisa was built with those requirements embedded into every interaction. Over time, the team found that automated outreach improved consistency on required disclosures and reduced risk, creating a more reliable and auditable front-end experience for learners and partners alike.
“It is significantly easier to sleep at night knowing that Lisa is doing all of our compliance statements,” says Michaelson. “With human agents, we have to coach and reinforce that daily. With Lisa, we get that consistency by d“It is significantly easier to sleep at night knowing that Lisa is doing all of our compliance statements. With human agents, we have to coach and reinforce that daily. With Lisa, we get that consistency by default.”
- Crystal Michaelson, Quality Improvement Manager at Boundless Learningefault.
The first version of Lisa was tightly scripted. This gave the Boundless Learning team confidence in early deployment, especially around compliance and messaging. As they observed real conversations, Boundless Learning worked with Observe.AI to gradually give the agent more flexibility to respond naturally to learners.
“What we learned was that the more freedom we allowed the AI to respond to how learners were actually engaging, the better the conversations became,” says Lomas.
As the agent evolved, Boundless Learning refined pacing, tone, and conversational flow. The result was outreach that felt more natural, handled a wider range of responses, and created more productive handoffs to human advisors.
The team also discovered that learners were more open in explaining their situation to the AI agent, whether that meant sharing updated goals, current enrollment elsewhere, or reasons they were no longer pursuing a particular path. That insight helped Boundless Learning maintain cleaner records and better understand learner intent across their partner network, improving how institutions engage and support learners over time.
Creating more opportunities for learner progress without added burden
By using AI agents to handle high-volume initial outreach, Boundless Learning expanded the number of learners who could be engaged without pulling advisors away from complex, high-touch conversations.
In practice, this meant more learners reached at the right moment, more opportunities created for advisors to step in when human judgment mattered, and a smoother path for prospective students to get guidance on programs and next steps.
“We’ve been able to create meaningful opportunities for people who otherwise may not have connected with us again,” says Martin. “And we’ve done that without reassigning staff or changing how advisors focus their time.”
“We’re excited about how AI can help us remove friction across the learner journey. When we can take administrative weight off our teams and be more proactive with students, everyone wins.”
- Chris Martin, Enrollment Operations Manager, Acquisition & Retention
With proactive outreach established as a foundation, Boundless Learning is now exploring additional ways AI can support learners throughout their journey, from enrollment reminders to follow-ups that help students stay on track academically.
The long-term vision is not just more outreach, but better-timed, more supportive engagement that helps learners move forward with confidence.
“We’re excited about how AI can help us remove friction across the learner journey,” says Martin. “When we can take administrative weight off our teams and be more proactive with students, everyone wins.”
