Sit Down Startup

Adam O'Donnell
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Here’s how to startup. Even when the world goes topsy-turvy. From one home office to another, Zendesk leaders chat with founders, CEOs, and makers on their startup journey. There’s rule-flipping, new dogma and recycling failure into growth. Plus, why customer experience is at the heart of success, as told by people who know unpredictability inside out. (That seems pretty helpful right now.)

  1. 12/02/2025

    [$10M+ Raised] Mark Doble, Co-Founder of Alexi, on Overcoming Adversity and Achieving Product-Market Fit in Legal Tech

    Welcome back to this week’s episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Mark Doble, Co-Founder of Alexi, to explore his inspiring journey in the legal tech space and the challenges of achieving product-market fit while raising over $10 million in funding. Join us as Mark shares his experiences transitioning from law to entrepreneurship, the pivotal moments that tested his resolve, and how Alexi is revolutionizing legal research through innovative AI solutions. He emphasizes the importance of conviction, adaptability, and understanding market needs in building a successful startup. (00:00:00) The Low Points: Overcoming Adversity in the Early Days of Alexi (00:03:40) From Law School to Startup: Finding the Path to Entrepreneurship (00:09:23) The Turning Point: Achieving Product-Market Fit with Customer Validation (00:15:40) First Principles Thinking: Innovating in Legal Tech Beyond Conventional Wisdom Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk for six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    19 min

  2. 29/01/2025

    [Harnessing AI Technology for Business Growth] Founder Daniel Saks Discusses Persistence, Overcoming Rejection, and the Evolution of AppDirect and Landbase

    In the latest episode of Sit Down Startup, Adam O'Donnell sits down with Daniel Saks, co-founder and CEO of Landbase, to delve into his entrepreneurial journey, including the successes and challenges he faced while building AppDirect. Daniel shares invaluable insights into the evolution of AppDirect, which has grown into a unicorn valued at over half a billion dollars, and how those experiences shaped his current venture, Landbase. Discover the pivotal moments during the early days of AppDirect, including the struggle to achieve product-market fit and the lessons learned from facing rejection. Daniel discusses the transformative potential of agentic AI in generating predictable pipelines for businesses and how his team is working to address the pain points of lead generation for startups. Tune in for an engaging conversation about resilience, innovation, and the importance of maintaining conviction in your vision as a founder. (00:00:19) The Early Entrepreneurial Spirit and Building AppDirect (00:10:05) Overcoming Challenges on the Path to Product-Market Fit (00:19:18) The Role of Agentic AI in Modern Business Strategies (00:23:08) Insights on Conviction, Resilience, and the Future of Startups Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk for six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    22 min

  3. 15/01/2025

    [Sustaining Competitive Edge] CEO Randy Wootton of Maxio on the Dynamics of Product-Market Fit in a Changing Landscape

    Welcome back to this week’s episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Randy Wootton, CEO of Maxio, to delve into the intricate dynamics of sustaining product-market fit in the ever-evolving landscape of B2B SaaS. Join us as Randy shares his unique journey from military leadership to the helm of a transformative billing and revenue management company. He discusses how Maxio is redefining the standards of product-market fit, particularly in a market increasingly influenced by AI and changing customer needs. Randy highlights the critical importance of continuous adaptation, competitive differentiation, and the metrics that truly matter for long-term success. (00:00:15) The Journey of Maxio: Merging Innovation with Customer-Centric Solutions (00:04:39) Understanding Product-Market Fit: A Continuous Journey, Not a Destination (00:12:29) Metrics that Matter: Navigating Growth and Retention in B2B SaaS (00:21:31) Listening to the Market: How Maxio Adapts to Changing Customer Demands Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk for six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    23 min

  4. 11/12/2024

    [$121.5M in Funding] Efficient Capital Labs' Kaustav Das on Bridging the Funding Gap and Achieving Product-Market Fit

    Welcome back to Sit Down Startup! In this week's episode, host Adam O'Donnell sits down with Kaustav Das, co-founder of Efficient Capital Labs, a pioneering venture focused on transforming funding for SaaS founders. Join us as Kaustav shares his remarkable journey in navigating the complexities of cross-border financing and the critical importance of achieving product-market fit. Discover the invaluable insights Kaustav gained about understanding customer pain points, the challenges of raising capital, and the strategic pivots that led to his company's success. Learn how Efficient Capital Labs, which has raised over $120 million, is bridging the funding gap and empowering SaaS founders to thrive in a competitive landscape. (00:01:10) The Journey Begins: Researching the SaaS Landscape (00:07:45) Understanding Customer Pain Points: The Key to Product-Market Fit (00:15:20) Navigating Cross-Border Funding Challenges (00:22:00) The Transformative Moment: From Idea to Execution Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk for six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    25 min

  5. 27/11/2024

    [Pioneering Retail Innovation] CEO Angie Westbrock on Standard AI's Journey from Autonomous Checkout to Computer Vision Insights

    Welcome back to this Thanksgiving week's episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Angie Westbrock, CEO of Standard AI, to explore her inspiring journey from the manufacturing sector to leading a cutting-edge retail technology company. Discover how Standard AI pivoted from autonomous checkout to leveraging computer vision for retail analytics, unlocking valuable insights for retailers. Angie shares her experiences navigating the challenges of product-market fit, the importance of understanding customer needs, and the strategic decisions that led to their recent success. (00:00:15) The Evolution of Standard AI: From Autonomous Checkout to Computer Vision (00:04:39) Navigating the Pivot: Lessons Learned as a New CEO (00:12:29) The Discovery Phase: Balancing Research and Execution (00:21:31) Understanding Customer Experience: Shifting Focus in B2B Markets Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk for six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    28 min

  6. 13/11/2024

    [$30M Raised] Transforming Legal Tech: Spellbook Co-Founder & CEO Scott Stevenson on Achieving Product-Market Fit

    Welcome back to Sit Down Startup! In this week's episode, host Adam O'Donnell sits down with Scott Stevenson, co-founder and CEO of Spellbook, the first generative AI copilot for lawyers, to discuss his remarkable journey in the legal tech space. Uncover the invaluable insights Scott gained about resilience, the struggles of achieving product-market fit, and the transformative power of large language models in revolutionizing legal document management. Learn how Spellbook, which has raised over $30 million, found its breakthrough after years of iteration and perseverance. (00:01:12) Overcoming Legal Fees: The Inspiration Behind Spellbook (00:06:30) The Loneliness of the Founder: Facing Investor Pressure (00:12:28) The Aha Moment: Discovering the Power of LLMs (00:19:40) The Importance of a Clear Marketing Message Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk for six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    24 min

  7. 30/10/2024

    [Transforming Crypto Access] Co-Founder/CEO Driss Benamour on Building Exponential.fi and Overcoming Crypto Winter

    In this episode, Adam O'Donnell sits down with Driss Benamour, co-founder and CEO of Exponential.fi, to explore the journey of building a decentralized finance platform amidst the challenges of the crypto winter. Driss shares his insights on achieving product-market fit by focusing on user needs and simplifying access to DeFi investments. He discusses the importance of maintaining conviction during tough times and the pivotal moment that led to the creation of their innovative risk assessment tool, "Rate My Wallet." Tune in to learn how Exponential.fi is transforming the investment landscape for crypto holders. 00:00 - Introduction to Exponential.fi and its mission to simplify DeFi access01:17 - Driss shares a low moment during the crypto winter and how they pivoted05:57 - The development and impact of the "Rate My Wallet" feature15:25 - Insights on achieving product-market fit and the importance of user feedback Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    25 min

  8. 10/10/2024

    [Navigating the AI Landscape] Co-Founder and CEO Jensen Harris on Textio's Journey and the Future of AI in Management

    In the latest episode of Sit Down Startup, Adam O'Donnell sits down with Jensen Harris, co-founder and CEO of Textio, to explore his remarkable journey in the world of AI-driven management solutions. Jensen shares how Textio has evolved over the past decade, transforming the way managers deliver feedback and recruit talent in an increasingly competitive landscape. Discover the challenges Jensen faced during the early days of Textio, including navigating the uncertainties of the COVID-19 pandemic, and learn how he and his team pivoted to adapt to a rapidly changing market. Jensen emphasizes the power of storytelling in marketing and how utilizing data-driven insights helped Textio connect with major enterprise clients. Tune in for an enlightening conversation about resilience, innovation, and the continuous quest for product-market fit in the tech industry. (00:00:19) AI Solutions for Feedback and Team Management (00:10:05) Enhancing Recruitment and Team Management Through AI (00:19:18) Data Storytelling for Customer Engagement Strategy (00:23:08) Personalized Enterprise Sales Approach with Data-Analytics Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    26 min
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Información

Here’s how to startup. Even when the world goes topsy-turvy. From one home office to another, Zendesk leaders chat with founders, CEOs, and makers on their startup journey. There’s rule-flipping, new dogma and recycling failure into growth. Plus, why customer experience is at the heart of success, as told by people who know unpredictability inside out. (That seems pretty helpful right now.)

Ficha técnica

  • Creado por
    Adam O'Donnell
  • Años en activo
    2020 - 2025
  • Episodios
    105
  • Clasificación
    Apto
  • Derechos de autor
    © Zendesk 868329
  • Sitio web del podcast
    Sit Down Startup