Oh, Shift! Where AI Meets SaaS Leaders cover art

Oh, Shift! Where AI Meets SaaS Leaders

Oh, Shift! Where AI Meets SaaS Leaders

Written by: Rick Watson
Listen for free

About this listen

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 chapter, this series is for you. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpCopyright 2025 Rick Watson Economics Politics & Government
Episodes
  • From Best-Kept Secrets to AI Operating System: How OneStock Is Industrializing Agents
    Jan 7 2026

    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





    This podcast uses the following third-party services for analysis:

    Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
    Show More Show Less
    42 mins
  • From Code to Outcomes: Yotpo’s Tomer Tagrin on Authentic AI, Agents, and Trust
    Dec 17 2025

    “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.



    This podcast uses the following third-party services for analysis:

    Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
    Show More Show Less
    33 mins
  • The QA Mindset That Companies Need To Adopt For The AI Future with Jason Cottrell
    Nov 19 2025

    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



    This podcast uses the following third-party services for analysis:

    Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
    Show More Show Less
    44 mins
No reviews yet