How Can AI Transform Learning And Development with Leslie Kelley

What happens when organizations say upskilling is a priority—yet fail to deliver beyond day one?

In this episode of The Future of Less Work, host Nirit Cohen sits down with Leslie Kelley, Chief Growth Officer at Absorb Software, to explore why traditional upskilling isn’t cutting it—and what smarter, business-aligned learning looks like. Drawing on findings from Absorb’s new State of Upskilling 2025 report, Leslie explains why only 44% of companies offer training at onboarding, fewer than 10% continue when business needs shift, and why ownership of learning remains so fragmented.

Together, Nirit and Leslie unpack how AI can eliminate the “boring parts” of jobs while personalizing skill pathways, why the half-life of skills is shrinking fast, and how Gen Z is redefining career growth around learning velocity—not promotions. They also highlight why mentorship, coaching, and people-based learning remain the human edge in a digital-first workplace.

If you’ve ever wondered how to close the gap between intent and action in L&D—and how to build learning cultures that actually drive performance—this conversation offers both a reality check and a roadmap for what’s next.

https://youtu.be/oEqT6EyER-4

Guest Information:

Leslie Kelley is the Chief Growth Officer at Absorb Software, where she spearheads innovative growth strategies across product, sales, marketing, customer success, and account management.
With a proven track record in driving revenue and customer satisfaction from Seed through Series E, Leslie excels in aligning complex platforms with customer value. Her expertise spans revenue generation, business strategy, and cross-functional team leadership.
Prior to joining Absorb, Leslie held pivotal roles at 360Learning, SmartRecruiters, and ThirdChannel, where she consistently delivered exceptional results in sales and customer success. Leslie is passionate about challenging the status quo and building bold strategies that deliver unparalleled value to customers.

Upskilling report: https://www.absorblms.com/white-papers/state-of-upskilling-report/

Chapters:

00:00 – Why Is Upskilling Failing Beyond Onboarding?
01:30 – How Can AI Personalize Learning and Skills?
03:40 – Why Doesn’t Upskilling Stick in Organizations?
05:07 – Who Really Owns Employee Upskilling?
06:40 – Why Don’t Leaders Prioritize Learning Time?
08:43 – How Can Upskilling Align with Business Outcomes?
10:24 – What Role Does Culture Play in Learning with AI?
12:27 – Why Is People-Based Learning Still Essential?
14:06 – How Can L&D Drive Business Strategy?
16:14 – What Makes Strategic Learning Collaboration Work?
18:03 – How Can Companies Balance Oversight and Agility in Training?
19:53 – What Does Always-On Upskilling Look Like?
20:56 – How Can Leaders Tie Learning Directly to Business Outcomes?
22:59 – Should Companies Train Customers and Partners Too?
24:16 – What Will Learning Look Like in the Next Few Years?
26:33 – Why Human Connection Matters in Future Learning
28:15 – What Question Should We Ask About the Future of Work?
29:56 – How Is Gen Z Changing Expectations Around Learning?