Oh, Shift! Where AI Meets SaaS Leaders

We Are Moving!

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. Well, now you can tune in on Wednesdays for the same great interviews and webinar conversations you've enjoyed here. Please take a moment right now to search for the Watson Weekly in your podcast player and hit follow. You don't want to miss our next conversation. Check the show notes for the link and thanks for making the shift with us. Watson Weekly – Apple Podcast: https://podcasts.apple.com/us/podcast/the-watson-weekly-your-essential-ecommerce-digest/id1577388393 Watson Weekly – Spotify: https://open.spotify.com/show/3oJL7jnlDFwJdqQPYD1oS5

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

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 Marudur, VP of Strategy at OneStock, a founder-led order management platform used by retailers to orchestrate complex omnichannel operations. Karthik’s a veteran of retail tech and supply chain—he helped build large-scale OMS programs and brings a pragmatic, ‘business-problem-first’ view to AI. We go inside a founder-led Order Management Software company where a quiet internal bot has already rewired sales, support, and product—and a new ‘config agent’ aims to turn six months of set-up into minutes. If you’re leading teams through AI without rewriting everything, this one’s for you. OneStock's AI initiatives include a configuration agent that compresses traditional setup times from months to minutes by dynamically configuring and simulating order workflows, improving operational efficiency and profitability. They build a data lake from sources like Confluence and Jira to power AI tools that assist sales, marketing, product, and development teams. Security and privacy are managed carefully, with legal teams involved in testing. Marudur emphasizes the importance of measuring the adoption and ROI of AI tools, maintaining agility in technology choices, and evolving from internal experimentation to co-innovation with customers.  The discussion also covers the emerging role of MCP in providing contextual, conversational AI experiences beyond traditional APIs. The episode highlights a pragmatic, business-focused approach to integrating AI in SaaS retail solutions, advocating for starting small, learning continuously, and aligning AI efforts with real business outcomes. #Ohshift #ai #ordermanagement #agent

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

“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 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: Tomer Tagrin, Co-Founder and CEO of Yotpo, explores Yotpo's comprehensive reset in culture, strategy, product development, and go-to-market approaches driven by AI and post-COVID realities.  Emphasizing authenticity as a superpower, Yotpo focuses on building trust with customers and agents in an AI-first world, particularly through enhancing reviews and loyalty programs.  Tagrin acknowledges execution challenges, and Yotpo divested some products to focus on core strengths.  AI is transforming engineering roles, accelerating coding, prototyping, and customer feedback analysis, while also reshaping support and sales functions.  Yotpo has invested in external expertise to improve product development and is experimenting with agentic commerce to adapt to new market dynamics.  The interview highlights the importance of culture change, transparency, and continuous learning within the company. It also discusses the future of commerce across multiple channels and interfaces, such as voice, and stresses the need for brands to maintain authenticity amid increasing AI-driven interactions.  Tagrin advises leaders to embrace change, remain humble, and focus on long-term growth despite short-term challenges.

The QA Mindset That Companies Need To Adopt For The AI Future with Jason Cottrell

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 Cottrell, CEO of Orium and incoming president of the Mach Alliance, discusses the profound shift AI is causing in business culture, hiring mindsets, and workflows, comparing it to past pivots like Agile adoption. He stresses that managing change is harder than the technology itself due to initial fear and hesitancy. Orium has adopted a forward-leaning strategy to stay ahead, integrating AI into workflows and emphasizing the QA mindset crucial for building reliable AI agents.  Jason outlines a four-stage employee progression model for AI adoption—from resistance to transformative use—and highlights peer learning and safe environments as key to advancing adoption. He notes challenges such as enterprise AI bans and evolving governance, advocating for cross-functional teams with autonomy to execute AI strategies.  As Mach Alliance president, he aims to guide members through AI and agentic ecosystem development, anticipating changes in membership criteria to reflect AI's growing role.  Overall, the discussion emphasizes rethinking processes with AI at the core rather than simple tool insertion, and the importance of leadership in navigating this transformative era. #ohshift #machalliance #culture

How Elastic Path Uses Paved and Unpaved Roads To Grow AI Adoption with Bryan House

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 storefront development and enhance merchandiser workflows via natural language prompts. How AI accelerates product development and prototyping, improving communication between product managers and engineers. He discusses potential AI challenges, including managing probabilistic AI outputs, ensuring agent authentication to prevent fraud, and balancing speed with accuracy in user experiences. The company fosters AI adoption by providing 'paved roads'—standardized tools—while allowing innovation through 'unpaved roads.' Tools like Replit and Lovable help users at different skill levels with AI integration.