Ask Ashley

Maddie Smiley
  • 5.0 (1)
  • ENTREPRENEURSHIP

Ask Ashley is a monthly podcast produced by Montgomery Entertainment LLC (ME), a boutique events agency based in the San Francisco Bay Area. CEO Ashley Montgomery and her team invite you to join their discussion on various creatively curated themes related to business, finance, leadership, entrepreneurship, and more!

  1. 06/17/2025

    The Real Role of AI in Marketing (and Life)

    AI is everywhere, but how do we use it without losing our human touch? In this episode of Ask Ashley, digital marketing strategist Maddie Smiley joins Ashley Montgomery to unpack the evolving role of AI in both work and daily life. From managing client expectations in a fast-moving industry to outsourcing meal planning with ChatGPT, Maddie shares a refreshingly honest take on where AI helps—and where it still falls short.

    35 min

  2. 03/25/2025

    Laughing Through Life

    In this episode of Ask Ashley, we sit down with comedian Jeff Applebaum to talk about the power of humor, his journey in stand-up comedy, and the unexpected lessons he's learned along the way.

    43 min

  3. 03/07/2025

    Elevating Customer Success

    In this Ask Ashley episode, we explore the world of Customer Success—what it really means, why it’s crucial for business growth, and how to build lasting relationships that drive retention.

    33 min

  4. 01/28/2025

    Thriving in the Remote Work Era

    In this episode of Ask Ashley, we dive into the evolving world of remote work and share strategies to help you thrive. From boosting productivity and building meaningful connections to enhancing collaboration and maintaining a healthy work-life balance, Ashley and Jack explore practical tips and insights for success in the remote era. This podcast is an extension of Montgomery Entertainment, LLC. For more, visit montgomeryentertainment.net.

    28 min

  5. 12/17/2024

    Mastering Sales Development: Part 3

    In Part 3 of our conversation with Sean, we wrap up our discussion on everything sales development! 🚀 The two discuss the importance of onboarding and training, and compensation strategies for sales teams. This podcast is an extension of the Montgomery Entertainment, LLC brand. For more, visit ⁠montgomeryentertainment.net.

    21 min

  6. 11/28/2024

    Mastering Sales Development: Part 2

    In Part 2 of our conversation with Sean, we dive even deeper into the world of sales development! 🚀 Sean shares actionable insights on mastering outreach strategies, leveraging AI tools effectively, and setting your team up for long-term success. Whether you’re leading a team or just starting in sales, this episode is packed with tips to help you work smarter, close deals faster, and build lasting relationships. This podcast is an extension of the Montgomery Entertainment, LLC brand. For more, visit ⁠montgomeryentertainment.net.

    29 min

  7. 10/30/2024

    Mastering Sales Development: Part 1

    On this episode of Ask Ashley, we dive into the world of sales development with Sean, a seasoned expert in building high-performance sales teams and effective strategies. Sean shares insights on structuring a successful sales development process, the qualities to look for when hiring top talent, and how to evaluate candidates for long-term success. We also explore how AI is reshaping prospecting and what sales teams can do to stay ahead in an evolving landscape. Whether you’re a sales professional or a business leader, this episode is packed with actionable tips to boost your sales strategy! This podcast is an extension of the Montgomery Entertainment, LLC brand. For more, visit ⁠montgomeryentertainment.net.

    30 min

  8. 09/25/2024

    Mastering Event Registration: Insights with Michael

    In this episode of Ask Ashley, we sit down with Michael, a seasoned events and registration expert. Michael shares his journey from the hospitality industry to becoming a freelance event professional. We dive into the intricacies of event registration, including platform selection, managing client expectations, and streamlining processes for large and small events. Michael also shares valuable insights on optimizing attendee experiences and engaging them from the moment they arrive. Tune in to learn key tips for successful event registration and management! This podcast is an extension of the Montgomery Entertainment LLC brand. For more, visit montgomeryentertainment.net.

    28 min
See All (18)

About

Ask Ashley is a monthly podcast produced by Montgomery Entertainment LLC (ME), a boutique events agency based in the San Francisco Bay Area. CEO Ashley Montgomery and her team invite you to join their discussion on various creatively curated themes related to business, finance, leadership, entrepreneurship, and more!

Information

  • Creator
    Maddie Smiley
  • Years Active
    2023 - 2025
  • Episodes
    18
  • Rating
    Clean
  • Copyright
    © Maddie Smiley
  • Show Website
    Ask Ashley