"The secret is you don't let the old man in." - Sam Allen, quoting Clint Eastwood

In his first official interview as CEO of Iterable, Sam Allen joins host Jacqueline Freedman for an unfiltered conversation on leadership, AI, and the future of marketing technology. 

Drawing on lessons from the Marine Corps and Salesforce, Sam shares his philosophy of servant leadership, why AI should act as a marketer’s co-pilot, and how companies can move beyond “vendor” status to become trusted advisors. He also reveals his strategic vision for Iterable’s future and what CMOs must do to stay relevant in today’s fast-changing Martech landscape. 

If you’re a marketing leader navigating AI disruption, growth, or organizational change, this episode is for you.

Highlights

• How servant leadership and radical transparency build resilient teams.

• Why AI should empower marketers as a co-pilot, not a replacement.

• The strategic vision behind Sam Allen’s move to Iterable.

• How to win the AI talent war by prioritizing culture.

• Practical steps to strengthen marketing and sales alignment.

• Why Martech stack consolidation is key for long-term growth.

Timestamps

• 00:00 – Introduction & Guest Welcome

• 00:43 – Rapid Fire Questions

• 03:42 – Leadership & Personal Insights from the Marine Corps

• 05:33 – Transition to CEO of Iterable

• 09:24 – AI & Innovation at Iterable (Nova)

• 14:11 – Ethics & the AI Talent War

• 18:04 – Moving Beyond Vendor Status with Customer Relationships

• 20:02 – Navigating Budget Constraints

• 21:07 – Standing Out in a Competitive Market

• 22:33 – Personal Insights & Martial Arts

• 23:04 – The Future of Marketing Technology

• 25:13 – Ethical Considerations in AI

• 32:31 – Advice for CMOs & Marketing Leaders

• 37:23 – Podcast Recommendations & Closing Remarks

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