Simplify, Streamline, Automate
Episode Overview
Sean and Ari sit down with Bob Strong, AVP of Service Operations at Assurant, to talk about what it really looks like to run IT service teams in an AI-first world. Bob shares how automation and virtual agents are improving resolution quality, accelerating documentation, and reshaping frontline roles while also touching on a hard truth: AI is only as good as the knowledge and governance behind it.
Key Takeaways
- AI is making automation “front and center” by taking on the grunt work that used to consume human bandwidth. Bob describes how agents can handle repetitive effort like summarizing tickets, drafting resolutions, and accelerating troubleshooting, allowing frontline teams to focus more on customer outcomes.
- The IT job isn’t disappearing; it’s changing into “AI agent management.” As virtual agents become part of daily operations, Bob explains how service teams are learning to validate outputs, guide the agent down the right path, and continuously improve workflows based on what the bot did well (or missed).
- Knowledge quality becomes a make-or-break dependency for agentic success. One of Bob’s biggest lessons: legacy knowledge content is often outdated, overly verbose, and written for humans rather than execution. To make AI useful, teams need a feedback loop that prevents agents from repeating failed troubleshooting paths.
- Deflection changes your service desk metrics, because the work that remains is harder. As bots handle the simple break-fix issues, the calls that reach humans trend toward novel, complex problems. That shift forces a rethink of productivity metrics (less “how many calls,” more “did we solve it?”) and supports a more “white glove” service model for high-impact cases.
- The north star is experience, and CSAT has to evolve to match conversational service. Bob shares how Assurant is exploring CSAT measurement that feels native to the interaction (lightweight, conversational feedback instead of yet another post-ticket survey) with the goal of capturing more signal without exhausting users.
FAQ
Q: How does AI change the day-to-day experience for frontline service teams?
A: Bob explains that AI can remove a lot of operational friction (drafting documentation, summarizing incidents, and supporting troubleshooting) which helps agents resolve issues faster and more consistently. But it also shifts responsibility: humans still provide context, validate outcomes, and guide the agent until trust is earned.
Timestamp: 3:20–4:48, 10:36–11:31
Q: What’s the biggest hidden blocker to getting value from virtual agents?
A: Knowledge. Bob points out that many organizations have years of outdated or human-oriented documentation still active in their systems, and bots will surface it unless it’s cleaned up. Modernizing knowledge into clearer, action-oriented steps (and removing irrelevant legacy content) is essential for reliable agent performance.
Timestamp: 6:45–7:40, 14:20–15:04
Q: How should IT leaders measure success as bots deflect more tickets and calls?
A: Bob’s primary measure is customer satisfaction (CSAT), and he emphasizes making it part of the interaction rather than relying on traditional surveys. He also notes that deflection changes the nature of human-handled work, which means success should be measured by outcomes and quality, not volume or speed alone.
Timestamp: 16:23–18:31
