There are two things most organizations skip when deploying Microsoft Copilot — and they happen to be the same two things that made Charles Schwab's rollout work.

The first: structured discovery work done before a single license goes wide. Not assumptions about what employees need — actual conversations across the business about what's broken, what's too manual, and what no tool has ever fixed. The second: getting IT and security in the room first, not last.

Howard Hecht, managing director of workplace technology at Charles Schwab, led the Microsoft Copilot rollout. He explains the discovery process Insight guided them through, how they structured training in deliberate layers, how they handled the "AI is taking my job" anxiety with data instead of talking points, and the real employee wins that made the case across the organization — including a marketing campaign that went from four weeks to 30 minutes, and a team member with dyslexia who described Copilot as brightening up her day.

If you're planning a Copilot deployment or trying to get more out of one that hasn't landed the way you hoped, this is the blueprint. JUMP RIGHT TO…

– 00:00 Welcome + cold open: Why the security team got the first Copilot licenses

– 00:47 Introduction and episode overview

– 02:19 The scale: where Schwab is today and where they're headed

– 02:36 What drove the decision to move forward with Copilot

– 04:42 Why Schwab partnered with Insight instead of going direct to Microsoft

– 05:32 The homework no one does — mapping real problems before a single license goes out

– 06:33 Early win: from a four-week campaign to 30 minutes

– 08:10 A second early win: Copilot and accessibility

– 08:48 Addressing the "AI is taking my job" anxiety

– 11:51 The move Howard is most glad they made upfront

– 13:21 What this rollout would have looked like without Insight

– 17:47 Where Copilot puts Schwab ahead of competitors

YOU'LL HEAR ABOUT:

• Why the security team got the first 20 Copilot licenses — and how that single decision changed the entire rollout trajectory

• The discovery process Insight guided Schwab through before any broad deployment

• How they structured training so it built real capability instead of just checking a box

• How to address the "AI is taking my job" anxiety with aggregate data instead of reassurances

What Charles Schwab Figured Out About AI Adoption That Most Companies Skip | EP 19