Shift AI Podcast
Hosted by Shift AI
Interviews with tech leaders and C-suite executives on the practical challenges and strategic impact of implementing AI at scale.
This is a weekly interview show focused on the practical application of artificial intelligence in business and government. Host Boaz Ashkenazy talks to CTOs, CEOs, and innovation chiefs from companies like Google, Slack, and MongoDB, as well as public sector leaders, to understand how they are implementing AI. The conversations go beyond hype, focusing on specific challenges like security, workforce training, and building user trust in high-stakes environments.
“Shift AI stands out by securing guests who are directly responsible for AI implementation at major companies and public institutions. The host's consistent, rapport-building interview structure elicits candid details about process, challenges with unions, and the cultural shifts required to make AI work.”
Who hosts this show
Boaz Ashkenazy hosts the Shift AI Podcast, where he interviews leaders about the impact of AI on the modern workforce. He is the CEO and co-founder of Augmented AI Labs and founder of Simply Augmented. His background includes experience at Meta, an early career in architecture, and co-founding several startups.
Credentials & credits
- CEO & Co-founder, Augmented AI Labs
- Founder & CEO, Simply Augmented
- Senior Director AI Infra, Redapt
- Former Product Manager, Meta
- Board of Trustees, Seattle Chamber of Commerce
- Seattle Chapter President, Applied AI Association
Other ventures
- Simply Augmented
- Augmented AI Labs
- Clause
- SuperSmall
- Studio 216
What kind of podcast
- Country
- United States
- Region
- usa
When new episodes drop
- 01AI, Security, and the Courage to Reinvent with Smartsheet CTO Cynthia TeeJun 26, 2026 · 31 min
- 02Building the AI-First City with San Jose Chief Innovation Officer Stephen CainesJun 16, 2026 · 40 min
- 03Unprompted Intelligence in High-Stakes AI with Hebbia CTO Aabhas SharmaJun 9, 2026 · 33 min
- 04Systems Thinking is the Agentic Unlock with Google's LaSean SmithJun 3, 2026 · 54 min
- 05
- 06AI Agent Deployment and Real ROI with MongoDB Field CTO Pete JohnsonMay 15, 2026 · 32 min
- 07
- 08Agentic AI and the Future of Revenue Teams with Outreach CEO Abhijit MitraApr 23, 2026 · 29 min
Notable episodes
- 01Building the AI-First City with San Jose Chief Innovation Officer Stephen Caines
A case study on how a major US city is using AI as a 'force multiplier' for public services, including details on union negotiations and public-private partnerships.
- 02Unprompted Intelligence in High-Stakes AI with Hebbia CTO Aabhas Sharma
A deep dive into the architectural and cultural challenges of deploying AI in finance, explaining how to build trust by combining deterministic and non-deterministic systems.
- 03AI, Security, and the Courage to Reinvent with Smartsheet CTO Cynthia Tee
Provides a clear framework (Model, Copilot, Plugin) for how a major SaaS company integrated AI, with a focus on security and earning enterprise customer trust.
What you'll be asked on this show
Boaz Ashkenazy begins each interview by establishing the guest's personal and professional backstory, consistently asking for their origin story and their first-ever paid job. This rapport-building opening allows for a more grounded and relatable entry into complex topics. He then transitions to the core subject, using pre-interview research to ask specific, informed questions about the guest's work. He often probes for practical challenges, asking about user adoption, internal resistance, and surprising outcomes. A common technique is to summarize a guest's point before asking a follow-up question, which clarifies the topic for listeners and guides the narrative. Some interviews conclude with a signature closing question asking the guest to describe the future of work in two words.
The show is a one-on-one interview format led by host Boaz Ashkenazy. He consistently opens with two personal questions—the guest's origin story and their first paid job—to build rapport before diving into technical and strategic topics. He frequently paraphrases guest responses to confirm understanding and steer the conversation.
Questions Shift AI keeps coming back to
11 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when Shift AI reaches for it.
origin
2- Q.01
“Can you share your background and what led you to your current role?”
This is always the first question, used to establish the guest's credibility and career trajectory.
- Q.02
“Can you tell the audience about your company and its journey?”
Follows the personal introduction to provide context on the guest's organization.
personal
1- Q.01
“What was your very first paid job?”
Asked early in the conversation, this signature question serves as a personal icebreaker to build rapport.
craft
3- Q.01
“What are the specific challenges of implementing AI in a high-stakes environment like yours?”
This question pushes guests to move beyond generalities and discuss industry-specific hurdles.
- Q.02
“Can you give us some specific examples of how this technology is helping people?”
Used to ground the conversation in real-world impact and tangible benefits for end-users or constituents.
- Q.03
“For the end user, what does building trust in this system actually mean in practice?”
Focuses on the practical components and user experience needed to achieve adoption and reliance on AI.
process
1- Q.01
“How are employees or professionals reacting to these new tools and relationships with machines?”
Probes the cultural and human side of AI adoption, exploring user behavior and internal response.
controversy
1- Q.01
“Have you had to engage with unions or other organized labor groups, and how did that go?”
A pointed question asked when relevant to explore the practical, often difficult, negotiations around AI and jobs.
technique
1- Q.01
“How do you think about combining deterministic processes with non-deterministic AI?”
A technical question aimed at understanding the architectural philosophy behind the guest's AI systems.
future
2- Q.01
“What should I tell my kids to study to prepare for this new world of AI?”
A forward-looking question that connects the high-level discussion to future generations and skills.
- Q.02
“How would you describe the future of work and AI in two words?”
A signature closing question used in some episodes to get a concise, memorable takeaway.
Signature segments
- · Asking guests about their first paid job
- · Opening with the guest's career origin story
- · Asking for a two-word description of the future of work
Topics covered repeatedly
Who gets booked here
Guests are typically C-suite executives, founders, or senior directors directly involved in AI strategy and implementation. They come from a mix of established tech giants (Google, Smartsheet), high-growth startups (Hebbia), and public institutions (City of San Jose).
- Cynthia Teeon AI, Security, and the Courage to Reinvent with Smartsheet CTO Cynthia Tee
- Stephen Caineson Building the AI-First City with San Jose Chief Innovation Officer Stephen Caines
- Aabhas Sharmaon Unprompted Intelligence in High-Stakes AI with Hebbia CTO Aabhas Sharma
- LaSean Smithon Systems Thinking is the Agentic Unlock with Google's LaSean Smith
- Kurtis Kempleon The Agentic Platform Hiding in Plain Sight with Slack Senior Director of DevRel Kurtis Kemple
Where to find this show
Audience & reach
Sponsors mentioned in the episodes include Redapt and SuperSmall. The host, Boaz Ashkenazy, is listed as Senior Director of AI Infra at Redapt and a co-founder of SuperSmall, suggesting the podcast is a content marketing channel for his professional ventures.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
Pitch Shift AI
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People also ask
- What is the host's real name?
- The host is Boaz Ashkenazy.
- What is the format of the show?
- It is a weekly one-on-one interview podcast with leaders in technology and business.
- Is the Shift AI podcast still active?
- Yes, based on the recent episode dates, the podcast releases new episodes regularly.
- Who is this podcast for?
- It's for tech professionals, executives, and entrepreneurs interested in the practical application and strategic challenges of implementing AI.
- What makes this podcast different from other AI shows?
- It focuses less on AI hype and more on the specific, real-world implementation details from practitioners at major companies and institutions.
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
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