The Duct Tape Marketing Podcast: "Upskilling Your Team for What's Next"
Host: John Jantsch | Guest: Rob Levin
Release Date: February 26, 2026

Episode Overview

This episode explores the rapidly evolving landscape of talent management and team building for small and mid-sized businesses. Host John Jantsch interviews Rob Levin, serial entrepreneur, business growth expert, and co-founder of Work Better Now, about his latest book, The New Talent Playbook: The Ultimate Guide for Building Your Dream Team. The discussion centers on how talent challenges have shifted in recent years, the impact of generational differences and emerging technologies like AI, and actionable strategies for upskilling teams to drive growth in an increasingly remote, technology-driven business environment.

Key Discussion Points & Insights

1. The Changing Face of Talent Management

• Shift from Talent Crisis to Talent Shift:

  • Rob emphasizes that while headlines focus on mass layoffs and AI-driven job loss, SMBs face a talent shift—the real challenge is finding the right talent with the right mindset and experience, especially for roles requiring an "owner's mentality".
  • "A lot really changed in the pandemic. And the reason I wrote the book is, I saw how the talent market changed... but I also saw how business owners were still running the same talent playbooks as if it was 2016." (Rob Levin, 01:19)

• Generational Changes in Workforce Expectations:

  • Younger generations work differently and prioritize company culture more than previous generations.
  • Business owners must adapt to shifting expectations regarding work-life balance, learning opportunities, and culture.

2. The Hidden Talent Crisis in SMBs

• Mismatch Between Headline Trends and SMB Needs:

  • Despite mass layoffs and talk of a difficult job market for college graduates, SMBs struggle to hire talent with ownership mentality and relevant experience. Layoffs in big companies don’t always generate candidates suited for SMBs.
  • "The skill sets that you need to thrive in a large business are not necessarily the same skill sets that are needed in a small or mid sized business." (Rob Levin, 04:14)

• Remote and Global Talent Strategies:

  • Expanding the talent pool regionally and internationally (e.g., Latin America) is crucial.
  • Hiring remotely presents both challenges and opportunities in finding quality talent.

3. Upskilling as the New Imperative

• Determining Upskill Potential:

  • Business owners must identify new capabilities their companies need and assess whether current employees have the desire and aptitude to upskill.
  • "You have to recognize, well, what is it that you need? And then the question is, do I have somebody on the marketing team that is upskillable? Do they have the desire to learn something new?" (Rob Levin, 08:18)

• Embracing Accessible Training:

  • Abundant, mostly affordable external training resources exist—cited examples include HubSpot and CRM trainings.
  • Owners should invest in training but set clear expectations for applying new skills, and reward those who successfully upskill.

4. The Role and Impact of AI

• AI Demands a Mindset Shift:

  • Many leaders treat AI simply as a tool for automation but need to rethink organizational design and workflows altogether.
  • "At Work Better Now we're using the term 'AI first'… Not to use AI to improve an existing workflow, but let's have that workflow totally redesigned where AI is doing a lot of the heavy lifting." (Rob Levin, 11:13)

• Leaders Need Hands-On Experience:

  • "Every business owner needs to go through a hands-on AI course first... before you can start to look at people on your team." (Rob Levin, 09:33)

• From “Doing” to “Managing” the Work:

  • Employees will shift from performing manual tasks to overseeing and refining AI implementations—requiring new skills and perspectives.

5. Building and Sustaining Culture—Remotely

• Culture as a Defining Factor:

  • Company culture is more vital than ever, especially to attract and retain top talent from younger generations and remote teams.
  • Define and operationalize core company values in hiring, performance management, and daily communications.

• Managing Culture Remotely and Across Borders:

  • Overcommunication is essential (e.g., weekly staff meetings, continual updates, reiterating important information).
  • Key Performance Indicators (KPIs) are vital for clarity, accountability, and employee self-direction in remote setups.
  • "In a remote environment, KPIs are important period. But KPIs for every job and several KPIs when possible, for every single role in the company is extremely important because at least now you have something you can measure people on." (Rob Levin, 15:23)

• Clarity for Employees:

  • Many employees find KPIs helpful as they clarify expectations and provide a sense of how to succeed.

6. Overcoming Resistance and Fears

• Navigating Employee Fears About AI:

  • Employees may worry about AI making their jobs obsolete.
  • Transparent communication is crucial: “We’re providing the training. Your job is safe—in fact, your job's going to be more important than ever.” (Rob Levin, 21:04)

• Continuous Learning and Leadership Adaptability:

  • Leaders must be open to continuous feedback and be willing to revise their approach as technology, markets, and team needs evolve.

Notable Quotes & Memorable Moments

• On the need for a new playbook:

  • “Business owners were still running the same talent playbooks as if it was 2016 and a lot really changed in the pandemic.” (Rob Levin, 01:25)

• On generational perceptions:

  • “You and I are old enough to remember when you used to hear bosses say something like, ‘Oh, they’re lucky to have a job.’ ...That has totally changed.” (Rob Levin, 02:58)

• On upskilling and training:

  • “There’s so much good training out there. Much of it is low cost, if not free…” (Rob Levin, 08:59)

• On embracing AI:

  • “I think every business owner needs to go through a hands-on AI course first.” (Rob Levin, 09:33)
  • “We're now using the term 'AI first.' Not to use AI to improve an existing workflow, but to totally redesign the workflow so AI does the heavy lifting.” (Rob Levin, 11:16)

• On measuring success remotely:

  • “KPIs are as much for that employee as they are for us.” (John Jantsch, 16:47)

• On clarity and remote work:

  • “Overcommunication is critical when teams are remote – everything from weekly meetings to written updates and clear KPIs.” (Rob Levin, 14:22)

• On the opportunity and fear AI brings:

  • “With AI, we just hopefully are not going to have to add a lot of headcount. And yet, you know, we should see improved outcomes.” (Rob Levin, 21:09)

Timestamps for Key Segments

• Introduction & Talent Shifts (00:10–03:29)
• Generational Differences in the Workforce (03:29–04:12)
• The Hidden Talent Crisis for SMBs (04:12–05:57)
• Remote and Global Hiring Strategies (05:57–07:13)
• Upskilling: Process and Opportunities (07:13–10:44)
• AI and Rethinking Workflows (10:44–13:09)
• Company Culture and Remote Teams (13:09–16:24)
• KPIs and Clarity in Remote Work (16:24–18:05)
• AI as a Thought Partner (18:05–19:01)
• Post-publication Learnings & AI Mindset (19:01–20:49)
• Addressing Employee AI Anxiety (20:49–21:59)
• Overcoming Resistance, Final Thoughts & Resources (22:03–22:32)

Additional Resources

• The New Talent Playbook: Search for the title or find Rob Levin’s newsletter/podcast via Substack or other platforms.
• Work Better Now: Information on accessing nearshore/remote talent at workbetternow.com.

This episode is a valuable listen for leaders seeking to adapt their workforce strategies for the new realities of remote work, generational change, and AI. Levin offers both high-level perspective and practical tips for recruiting, upskilling, and empowering your team for business growth.