Hebba Youssef (I Hate It Here), Kailey Cartwright (SurveyMonkey), and Alex Simmons (Boon) explored:
HY
Hebba Youssef
Chief People Officer
I Hate It Here
KC
Kailey Cartwright
Global Lead, Learning & Development
SurveyMonkey
AS
Alex Simmons
Founder & CEO
Boon
What We Covered
AI is reshaping L&D faster than most teams can adapt. This session brought together HR leaders from I Hate It Here, SurveyMonkey, and Boon to discuss why AI-first strategies fail without culture, how L&D is evolving into reskilling engines, and what the future holds for coaching and career development.
Key Takeaways
1
AI isn't the strategy, mindset is
Adoption means nothing without cultural readiness.
2
L&D must evolve into Reskilling & Development
Replace rigid programs with agile, skills-first learning.
3
The manager role is being unbundled
Most can't coach 10+ directs, expect tech and third parties to fill the gap.
4
Career paths are going nonlinear
Skills > titles. Growth will be dynamic and AI-augmented.
5
Culture beats tooling
Power hours and Slack threads outperformed formal training in driving adoption.
What We Discussed
In this session, we explored:
Why "AI-first" strategies fall flat without curiosity, culture, and core competencies
How leading companies are reshaping L&D into reskilling engines
Real-world experiments in manager enablement, tool adoption, and org-wide upskilling
The future of coaching, career paths, and management itself
Leadership development is changing fast. We're helping teams rethink how they build adaptability, skills, and culture at scale.