DiscoverBold Moves: How Did You Know?What It Takes To Be First: Ashley Cheretes on Leading Prudential's AI Revolution
What It Takes To Be First: Ashley Cheretes on Leading Prudential's AI Revolution

What It Takes To Be First: Ashley Cheretes on Leading Prudential's AI Revolution

Update: 2025-10-07
Share

Description

We're live on Substack! Join us: kristenrocco.substack.com

Being the first is bold. No one has gone before you. There is no playbook. You are charting the course, sometimes confidently because of your immense conviction and sometimes courageously because your gut sense is leading you.

Being the first… that’s the theme of this episode with Ashley Cheretes, Director of Gen AI at Prudential Financial.

When Ashley applied for a new director of Gen AI role at her organization, this is exactly what she confronted: an interesting job description in an emerging space that no one in her organization–or anywhere else for that matter–had ever done before.

When you make your bold move, you’re going to be the first in some capacity. The steps to achieve your vision will look blurry.

I asked Ashley how she is navigating being the first to help us all in our Bold Move firsts. From keeping a "kudos folder" to overcome bad days to figuring out how to overcome her stakeholders’ hesitations about a new technology, she shares practices you can embrace to help you confidently lead and navigate the path when no one has gone before you.

Ashley teaches us her tips for:

  • Overcoming imposter syndrome.
  • What to do when you don’t have all the answers.
  • How to break through the status quo to influence change
  • And much more

This episode is a powerful two-for-one. You'll get actionable advice on the skills needed to be first in your bold move, alongside critical insights into AI from one of the industry's foremost experts. Ashley shares the same expertise she's brought to stages at Adobe Summit, The AI Leaders Forum, Boston University, and Vanguard, making this a can't-miss conversation.

Stay tuned until the end for her rapid-fire answers to your pressing questions about AI:

  • Where do you see AI being the most effective? What problems is it solving for businesses?
  • What are AI’s limitations?
  • What are the AI courses you recommend?
  • What’s the predictive capability of gen AI?
  • What’s Agentic AI?

Connect with Host Kristen Rocco

On Substack: https://kristenrocco.substack.com/

On LinkedIn: https://www.linkedin.com/in/kristenrocco/

Take the listener feedback survey: https://forms.gle/hBBKkKFVfbfzCFREA

Connect with Guest Ashley Cheretes

On LinkedIn: https://www.linkedin.com/in/ashleycheretes/

Comments 
In Channel
loading
00:00
00:00
x

0.5x

0.8x

1.0x

1.25x

1.5x

2.0x

3.0x

Sleep Timer

Off

End of Episode

5 Minutes

10 Minutes

15 Minutes

30 Minutes

45 Minutes

60 Minutes

120 Minutes

What It Takes To Be First: Ashley Cheretes on Leading Prudential's AI Revolution

What It Takes To Be First: Ashley Cheretes on Leading Prudential's AI Revolution