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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Most people in higher ed hear “AI in admissions” and think: “Ah, so… another chatbot.”
In this episode of The VineDown, I sit down with CollegeVine’s own CTO, Chris Coffey, to pull back the curtain on what we’re actually building: autonomous AI agents that act more like teammates than tools with guardrails, reasoning, and real responsibility.
We get into:
- How our first AI recruiter (“Sarah”) went from a wild experiment to an at-scale product engaging millions of students
- Why deploying AI in admissions is orders of magnitude harder than most people think
- What it really means to keep agents “safe” and why guardrails, tools, and moderation matter so much in higher ed
- How agents can triage student tasks (registering for classes, FAFSA, clubs, advising) and prioritize what’s urgent vs. what can wait
- Why Chris says “there’s nobody building agents the way we are building them right now”
- What CIOs get wrong about trying to build their own AI solutions
- And the agent Little Chris wishes he had in college (spoiler: it’s about unknown unknowns, not homework)
If you’ve ever wanted a clear, honest explanation of how AI agents actually work in a high-stakes environment like education (and what’s coming next) this one’s for you.
⏱️ Timestamps
00:00 – Cold open with Chris
02:05 – Meet Chris Coffey, CollegeVine CTO
03:00 – From AI recruiter “Sarah” to an agent platform
04:25 – Why deploying AI at scale is so damn hard
06:10 – Models leveled up. Our architecture had to, too.
08:00 – What “safe” actually means in an AI agent
11:45 – Agents, tools, and responsibilities (AI as a teammate)
14:30 – Long-running relationships: agents that support students for a year+
18:15 – How agents decide what’s urgent vs. what can wait
20:30 – Guardrails + reporting = less fear, more trust
21:55 – Inside Chris’s engineering philosophy
23:40 – Non-determinism: why agents are different from normal software
25:30 – A message to CIOs who want to “just build it themselves”
29:25 – The agent Little Chris wishes he had in college
31:30 – Unknown unknowns and the real value of student-facing agents
33:25 – Looking ahead: where agents and higher ed go next
33:55 – Emily’s closing + why this conversation matters
Listen to this special full episode of The VineDown wherever you get your podcasts!
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