Unstuck Pod

Jamie Schneiderman
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  • Entrepreneurship

Conversations with founders about their businesses and the challenges of being a founder, about what really stalls growth in B2B SaaS, and what to do about it.

  1. Jun 5

    Service Operations Not Lineups (Shannon Vander Meulen)

    In this episode, Jamie welcomes Shannon Vander Meulen, founder of WaitWell, to discuss the evolution of service operations and the innovative solutions that emerged during the pandemic. Shannon shares the WaitWell journey, transitioning from running a registry office to developing a robust service operations platform that optimizes customer experiences. The conversation explores the benefits of listening to customers, the challenges of balancing customer requests with product vision, and the importance of human connections in a digital world. Whether you’re a tech entrepreneur, service professional, or interested in optimizing operations, this episode offers valuable insights on navigating the complexities of service delivery. 🔗 Guest & Resources  Connect with Shannon Vander Meulen: https://www.linkedin.com/in/shannonvandermeulen/  Check out WaitWell: http://www.waitwellsoftware.com 🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com 📌 Chapters  00:00 – Welcome and Introduction to Shannon Vander Meulen  00:36 – Understanding WaitWell  01:43 – Shannon Vander Meulen's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging with WaitWell  19:56 – Final Thoughts and Key Takeaways  🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems 👉 Want to be on the podcast? Send an email to jamie@unstuckyourbusiness.com

    23 min

  2. Jun 3

    Make Firm Knowledge Work for You (Jeanne Hardy)

    In this episode, Jamie welcomes Jeanne Hardy, CEO and founder of Levvy, to discuss the evolution of business management for creative professionals and the technology supporting it. Jeanne shares her unique journey from an art school graduate to a tech founder, highlighting the gaps she identified in the marketplace for creatives and how she addressed them through Levvy. The conversation delves into the benefits of real-time visibility in operations and the challenges of transitioning from running an agency to leading a tech company. Whether you’re a security professional, a team leader, or simply curious about the intersection of creativity and technology, this episode offers valuable insights on leveraging technology to streamline business processes. 🔗 Guest & Resources  Connect with Jeanne Hardy: https://www.linkedin.com/in/jeannehardy/  Check out Levvy: https://signup.levvy.com/ 🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com 📌 Chapters  00:00 – Welcome and Introduction to Jeanne Hardy  00:36 – Understanding Levvy  01:43 – Jeanne Hardy's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging with Levvy  19:56 – Final Thoughts and Key Takeaways 🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems 👉 Want to be on the podcast? Send an email to jamie@unstuckyourbusiness.com

    24 min

  3. May 22

    Built for Essential Workers (Adam Greenberg)

    In this episode, Jamie welcomes Adam Greenberg from MakeShift to discuss the intricacies of workforce management in the healthcare sector. Adam shares his unconventional journey to becoming the CEO of MakeShift, where he emphasizes the importance of scheduling in managing shift workers. The conversation explores the benefits of a specialized approach to workforce management, particularly in regulated industries, and delves into the challenges of navigating complex compliance and operational needs. Whether you’re a security professional, team leader, or just curious about the future of workforce management, this episode offers practical insights into the evolving landscape of scheduling technology. 🔗 Guest & Resources  Connect with Adam Greenberg: https://www.linkedin.com/in/adamgreenberg2/  Check out MakeShift: https://www.makeshift.ca/ 🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com 📌 Chapters  00:00 – Welcome and Introduction to Adam Greenberg  00:36 – Understanding MakeShift  01:43 – Adam Greenberg's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging with MakeShift  19:56 – Final Thoughts and Key Takeaways  🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems 👉 Want to be on the podcast? Send an email to jamie@unstuckyourbusiness.com

    25 min

  4. May 21

    From Excel Sheet to SaaS (Wael Azar)

    In this episode, Jamie welcomes Wael Azar from In2 to discuss the journey of building a successful sports management platform. Wael shares the In2 story, starting from humble beginnings in Lebanon to now serving 400 clients across 21 countries. The conversation explores the benefits of digital transformation in sports management and the challenges faced in hiring and fundraising within the region. Whether you're a startup founder, tech enthusiast, or simply curious about the sports industry, this episode offers valuable insights into creating a thriving business in a competitive landscape. 🔗 Guest & Resources  Connect with Wael Azar: https://www.linkedin.com/in/wael-azar/  Check out In2: http://www.joinin2.com 🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com 📌 Chapters  00:00 – Welcome and Introduction to Wael Azar  00:36 – Understanding In2  01:43 – Wael Azar's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging with In2  19:56 – Final Thoughts and Key Takeaways  🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems 👉 Want to be on the podcast? Send an email to jamie@unstuckyourbusiness.com

    24 min

  5. May 6

    Business Owners Don't Know Their Value (Dylan Gans)

    In this episode, Jamie welcomes Dylan Gans from Baton to discuss the future of small business ownership and the challenges faced by entrepreneurs today. Dylan shares the Baton journey from its inception, highlighting the innovative solutions they've developed to help small business owners understand the value of their enterprises. The conversation explores the benefits of modernizing the business sale process, the role of AI in enhancing buyer experiences, and the importance of empowering new entrepreneurs. Whether you’re a small business owner, aspiring entrepreneur, or just curious about the evolving marketplace, this episode offers practical insights on navigating the complexities of buying and selling businesses. 🔗 Guest & Resources  Connect with Dylan Gans: https://www.linkedin.com/in/dylan-gans-8653639a/  Check out Baton: baton.com 🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com 📌 Chapters  00:00 – Welcome and Introduction to Dylan Gans  00:36 – Understanding Baton  01:43 – Dylan Gans's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging with Baton  19:56 – Final Thoughts and Key Takeaways  🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems 👉 Want to be on the podcast? Send an email to jamie@unstuckyourbusiness.com

    26 min

  6. May 5

    When Content Isn't Enough (Malcolm Friedberg)

    In this episode, Jamie welcomes Malcolm Friedberg to discuss the reinvention of sales and marketing in today's rapidly evolving landscape. Malcolm shares the GetGoaler journey from his extensive experience in marketing and demand generation, highlighting the significant shifts and challenges faced by professionals in the industry. The conversation explores the importance of getting people's attention in an era where traditional methods fall short, and how AI can serve as an amplifier, although it can't replace the fundamentals. Whether you’re a security professional, team leader, or just curious about the future of marketing, this episode offers practical insights on navigating the complexities of modern sales strategies. 🔗 Guest & Resources  Connect with Malcolm Friedberg: https://www.linkedin.com/in/malcolmfriedberg/  🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com 📌 Chapters  00:00 – Welcome and Introduction to Malcolm Friedberg  01:43 – Malcolm Friedberg's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging 19:56 – Final Thoughts and Key Takeaways  🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems 👉 Want to be on the podcast? Send an email to jamie@unstuckyourbusiness.com

    26 min

  7. Apr 22

    Never Be The Victim (Rob Desmond)

    In this episode, Jamie welcomes Rob Desmond from MagicOrange to discuss the intricacies of building successful sales processes in startup environments. Rob shares his journey from working in sales for over 25 years to providing advisory services for SaaS-based companies worldwide. The conversation dives into the importance of understanding sales as a process and how to identify the right market fit for your product. Rob also highlights the common pitfalls companies face, such as hiring too soon and setting unrealistic revenue targets. Whether you’re a security professional, team leader, or just curious about the future of sales strategy, this episode offers practical insights on navigating the challenges of early-stage growth. 🔗 Guest & Resources  Connect with Rob Desmond: https://www.linkedin.com/in/rdesmond/  Check out MagicOrange: http://www.magicorange.com 🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com 📌 Chapters  00:00 – Welcome and Introduction to Rob Desmond  00:36 – Understanding MagicOrange  01:43 – Rob Desmond's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging with MagicOrange  19:56 – Final Thoughts and Key Takeaways  🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems  👉 Want to be on the podcast? Send an email to jamie@unstuckyourbusiness.com

    24 min

  8. Apr 22

    From Survival to Strategy (Matthew Kaisaris)

    In this episode, Jamie welcomes Matthew, the CEO and founder of Boreal Systems, to discuss the journey of starting a consultancy in the rapidly evolving landscape of work management platforms. Matthew shares the Boreal Systems story, detailing his transition from working in the Monday.com ecosystem to launching his own business. The conversation explores the benefits of optimizing workflows and the impact of AI on project management. Matthew also delves into the challenges of initial growth and the shifting dynamics of client relationships in the digital age. Whether you’re a security professional, team leader, or just curious about the future of work management tools, this episode offers practical insights on navigating the complexities of the industry. 🔗 Guest & Resources  Connect with Matthew: https://www.linkedin.com/in/matthewkaisaris/  Check out Boreal Systems: https://www.borealsystems.ca 🤝 Connect with Me: https://www.linkedin.com/in/jamieschneiderman/  Unstuck Your Business: www.unstuckyourbusiness.com 📌 Chapters  00:00 – Welcome and Introduction to Matthew  00:36 – Understanding Boreal Systems  01:43 – Matthew's Journey and Insights  02:30 – Major Shifts in the Industry  04:11 – Key Technologies and Innovations  05:37 – Market Demands and Challenges  06:54 – Opportunities and Cautions in the Field  09:42 – Real-world Applications  11:13 – The Future of Content and Learning  12:17 – Insights on Collaboration and Teamwork  14:13 – Strategies and Best Practices  15:20 – Balancing Creativity and Growth  16:56 – Lessons Learned  18:24 – Engaging with Boreal Systems  19:56 – Final Thoughts and Key Takeaways  🔑 Keywords  startup finance, investor readiness, due diligence, financial modelling, startup reporting, fundraising preparation, SaaS metrics, tech founders, cash flow management, management accounts, financial operations, startup compliance, data room management, VC expectations, scaling finance systems  👉 Want to be on the podcast? Send an email to jamie@unstuckyourbusiness.com

    21 min
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About

Conversations with founders about their businesses and the challenges of being a founder, about what really stalls growth in B2B SaaS, and what to do about it.

Information

  • Creator
    Jamie Schneiderman
  • Years Active
    2K
  • Episodes
    28
  • Rating
    Clean
  • Copyright
    © 2026 Jamie Schneiderman