On-demand session · 34 minutes Recorded live at Convene 2026

What your CISO is looking for

Workforce risk in the AI era — a candid conversation for security awareness, training, and human risk management leaders who want a real seat at the leadership table.

Living Security CEO Ashley Rose sits down with Edna Conway — former Chief Security Officer of Cisco's Global Value Chain and Chief Security & Risk Officer for Microsoft Cloud — to unpack what boards and CISOs actually want from your program. Hint: it isn't completion rates.

Ashley Rose Ashley Rose CEO, Living Security
Edna Conway Edna Conway Security executive & advisor
Full session · 33:59
Why watch

Your program says people completed training. Your CISO hears activity — not risk.

Meanwhile the game has changed: AI agents now share your people's identities, permissions, and attack paths, and attackers move in seconds while most programs still report quarterly.

Ashley and Edna get specific about the gap between what awareness programs report and what leadership actually needs to see — and how to close it.

10% → 73%

Roughly 10% of your workforce drives 73% of your risk. Cyentia research

22 sec

The speed of an attacker handoff. Quarterly reporting can't keep up.

3

Questions every program should be able to answer for the board.

What you'll learn

In 34 minutes, you'll walk away knowing:

The framework

Activity tells you what people clicked. Risk tells you what could happen next.

Completions, click rates, thumbs-ups on training modules — none of it answers the questions leadership is actually asking. Edna, who has chaired boards and sits on risk and audit committees, asks the same four things every time.

If your program can't answer those today, this session is your homework.

01 What am I seeing?
02 How are you monitoring it?
03 How are you prioritizing it?
04 And tell me — with empirical data — the difference it's making.

— Edna Conway, on what she asks every program owner

Speakers

Two people who have sat on both sides of the table

Ashley Rose

Ashley Rose

CEO, Living Security

Ashley leads Living Security's mission to transform security awareness into AI-native human risk management — giving security teams visibility into workforce risk across humans and AI agents, in one view.

Edna Conway

Edna Conway

Security executive & advisor

Former Chief Security Officer of Cisco's Global Value Chain (228,000 third parties) and Chief Security & Risk Officer for Microsoft Cloud. Board director, risk and audit committee veteran, member of the U.S. Information Security and Privacy Advisory Board, and member of Living Security's Executive Advisory Board. A self-described straight shooter — and it shows.

From the session
“If I use this platform properly, I'm going to tell you how much revenue I protected. How many people I protected. How much innovation I protected. And they will stop and listen to that.”
Edna Conway
“If we keep bringing the same report to the board — we checked the box, everybody got trained, our phishing click rate dropped half a percent — we're not going to get the budget we're looking for.”
Ashley Rose
“I just saw this in the news — what are we doing about it? If you're reactive to that, you've already failed.”
Edna Conway

Ready to report risk instead of activity?

See how The Living Security Platform correlates behavior, identity, and threat signals to show workforce risk posture — humans and AI agents in one view — and proves your program is driving incidents down.

Get a demo Explore The Living Security Platform