Rick Watson

Oh, Shift! Where AI Meets SaaS Leaders

Business EN ↓ 10 episodes

The Oh Shift! podcast is no longer active, and future interviews will be displayed on https://www.watsonweekly.com/In a tech world bursting with hype, this new podcast cuts through the noise. The series features candid conversations with software C-Suite leaders—from seed-stage to public companies—who are navigating the seismic shift AI is bringing to product, marketing, and operations. Forget the fluff. These are real discussions about restructuring teams, evolving codebases, and embedding AI in company culture—without silver-bullet thinking. If you're leading a software company into the next...

Author

Rick Watson

Episodes

We Are Moving! 28.01.2026 0:42

Hi everyone! We have some exciting news. Over the last year, Oh Shift! has been the place where AI meets SaaS leaders. We want to streamline your listening experience. Instead of checking two different feeds, we're bringing everything under one roof. From now on, our leadership interviews are moving to the Watson Weekly. You might already know the Watson Weekly for its Monday eCommerce digest. Wel...

From Best-Kept Secrets to AI Operating System: How OneStock Is Industrializing Agents 07.01.2026 42:29

Welcome to the ninth episode of Oh, Shift!: Agentic Software Leader Series, where we cut through the hype and have candid conversations with software leaders navigating the seismic shift of the AI era. This series is designed for founders and operators who are focused on building internal AI momentum without relying on silver-bullet thinking. In this episode, host Rick Watson talks with: Karthik M...

From Code to Outcomes: Yotpo’s Tomer Tagrin on Authentic AI, Agents, and Trust 17.12.2025 33:12

“Change isn’t painful—resistance is. Today, Yotpo co-founder Tomer Tagrin shares how his teams ship outcomes over code, why 70% of support tickets are now deflected by AI, and how to keep authenticity and trust when LLMs are everywhere.” Welcome to the eighth episode of Oh, Shift!: Agentic Software Leader Series, where we cut through the hype and have candid conversations with software leaders nav...

The QA Mindset That Companies Need To Adopt For The AI Future with Jason Cottrell 19.11.2025 43:30

Welcome to the seventh episode of Oh, Shift!: Agentic Software Leader Series, where we cut through the hype and have candid conversations with software leaders navigating the seismic shift of the AI era. This series is designed for founders and operators who are focused on building internal AI momentum without relying on silver-bullet thinking. In this episode, host Rick Watson talks with: Jason C...

How Elastic Path Uses Paved and Unpaved Roads To Grow AI Adoption with Bryan House 05.11.2025 46:54

In this episode, host Rick Watson talks with: Bryan House, CEO of Elastic Path, discusses AI's transformative impact on commerce. OpenAI's instant checkout exemplifies AI's shift toward directly monetizing transactions, leveraging its vast user base and memory capabilities for personalized shopping. House discusses how ElasticPath embraces AI through Model Context Protocol (MCP) to streamline stor...

Agentic Merchandising and AI Native Startups with Vinod Kumar 22.10.2025 46:37

In this episode, host Rick Watson talks with: Vinod Kumar, CEO of Syntheum AI and formerly Head of Global Business Insights & Growth at Demandware/Salesforce CommerceCloud. He shares insights on leveraging AI in e-commerce and startups amid rapid technological change. He identifies trust as the top concern, emphasizing the need to earn and maintain it quickly to enable users to offload tasks t...

Empathetic Usage of AI Ensures Less Complexity and More Efficiency - With Alex Sayyah 08.10.2025 34:03

In this episode, host Rick Watson talks with: Alex Sayyah, CEO of Aleran Software, a B2B ecommerce platform tailored for industrial manufacturers, discusses the company's pivot from serving sales agencies to focusing on industrial manufacturers with complex sales needs. Aleran integrates AI tools, such as CPQ, PIM, and order management, atop ERP systems to streamline sales processes. Alex emphasiz...

How BetterCommerce Ended Siloed Information with Vikram Saxena 24.09.2025 36:19

In this episode, host Rick Watson talks with: Vikram Saxena, the Founder of BetterCommerce, a modular, composable B2B e-commerce platform designed for small to medium-sized businesses. Saxena has also worked at Vsworx Information Systems, HCL Technologies, and Axtrum Technologies (formerly BlueThread Solutions). This episode can be seen as an example of a developer/practitioner using AI to experim...

The Future is Less If Then And More Prompts, Agents, and MCP - A SVP Looks to the Future 10.09.2025 23:17

In this episode, host Rick Watson talks with: Shailesh Kumar, SVP of Engineering at Salesforce, is the Head of Engineering for Salesforce Commerce & Retail Cloud. He previously served as SVP and Head of Engineering at ClickUp and VP of Engineering at MuleSoft, both of which were acquired by Salesforce. This episode can be seen as an AI primer that will benefit those who listen to this wide-ran...

AI Adoption: From Skepticism to Evangelism - Lessons from a Tech CTO 03.09.2025 38:12

In this inaugural episode, host Rick Watson talks with: John Shao, Co-founder and CTO of Pipe17, a fast-growing player in the e-commerce order management space. John shares his journey from being an early AI adopter to becoming a company-wide evangelist for AI adoption. John discusses his experience with the wide range of employee reactions to AI, from those who find it game-changing to others who...