Upskilling Your Team for What’s Next

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Overview

In this episode of the Duct Tape Marketing Podcast, John Jantsch interviews Rob Levin, serial
entrepreneur, chairman and co-founder of Work Better Now, and author of
The New Talent Playbook: The Ultimate Guide for Building Your Dream Team.

With over 30 years of experience helping small and mid-sized businesses solve persistent
talent challenges, Rob shares why the traditional hiring “playbook” no longer works. He
explains how the pandemic, generational shifts, remote work, and artificial intelligence
have fundamentally changed the talent landscape.

The conversation explores the hidden talent crisis facing SMBs, why culture is more critical
than ever, how to rethink KPIs in a remote-first world, and what it really means to become
an AI-first organization. If you’re still managing talent like it’s 2016, this episode offers
a roadmap for building a future-ready team.

Guest Bio: Rob Levin

Rob Levin is a serial entrepreneur and business growth expert with more than three decades
of experience helping small and mid-sized businesses thrive. He is the chairman and co-founder
of Work Better Now, a company that empowers U.S.-based SMBs to access highly skilled remote
professionals, particularly from Latin America, to overcome hiring bottlenecks and build
high-performing teams.

Rob is the author of The New Talent Playbook: The Ultimate Guide for Building Your Dream Team,
where he outlines a modern approach to talent strategy in an era defined by remote work,
rapid technological change, and AI disruption.

Key Takeaways

1. The Talent Crisis Is Really a Talent Shift

Despite headlines about layoffs, many small and mid-sized businesses still struggle to fill
critical roles. The skills needed to succeed in large