Episode Overview

Podcast: The Digital Executive
Host: Brian, Coruzant Technologies
Guest: Jesse Lipson, Founder & CEO of Levitate
Episode Title: Jesse Lipson on Reinventing Relationship Marketing for Small Businesses | Ep 1153
Date: November 24, 2025

In this episode, Jesse Lipson shares insights on how Levitate is redefining relationship marketing for small businesses, especially in service- and relationship-driven industries like healthcare. The conversation dives into why authentic connections matter more than transactional marketing, the challenges small businesses (especially in healthcare) face, and how Levitate leverages a blend of software, services, and AI to help organizations nurture genuine relationships at scale.

Key Discussion Points & Insights

Redefining Relationship Marketing

• Inspiration from Real Life:
  Jesse shares that Levitate’s inspiration came from observing his wife's consulting business. Despite heavy investments in traditional marketing automation tools, meaningful business was coming through authentic, personal connections rather than those systems.
  Quote:

  “It kind of occurred to me ... there's a whole segment of the economy that really operates more on word of mouth and referral and just doing a good job kind of keeping in touch authentically. But the suite of sales and marketing software out there was all built for ... mass blast transactional type businesses … not really built for the way that a lot of businesses actually try to keep in touch with their customers.” — Jesse Lipson [02:19]

• Targeting Relationship-Based Industries:
  Jesse notes a gap in existing sales and marketing platforms, which often target transactional or e-commerce-based models, leaving service-oriented and referral-based small businesses underserved. Levitate aims to fill this gap.

Challenges and Opportunities in Healthcare Communication

• Healthcare’s Unique Communication Challenges:
  With the platform now HIPAA-enabled, Levitate is providing value to healthcare small businesses (e.g., chiropractic and dental practices). Healthcare providers often lack the time and expertise for building an online presence and engaging consistently with patients via content and communication channels.
  Quote:

  “They really are experts at providing care to patients and not necessarily staying up to date on ... best practices for showing up in search engines and ... communicate high value content to their patients and just to the public in general.” — Jesse Lipson [04:34]

• Beyond Tools: The Need for Content & Strategy:
  Small businesses not only need automation tools but also guidance and support in content creation and communication strategy. Levitate’s approach integrates both.

Software Plus Services: A Holistic Approach

• Support Beyond Technology:
  Jesse highlights the importance of combining human support with software for small business success.
  Memorable Analogy:

  “It’s kind of like the workout plan for your business, where you know it’s good for you in the long term, but in the short term you don’t necessarily always have time for it.” — Jesse Lipson [07:06]

• Partnering for Success:
  Levitate meets with clients, prepares content calendars, and aligns communication strategies with business goals, taking tasks off the plates of already overburdened teams.

The Future of Relationship-Driven Software & the Role of AI

• Vision for AI in Relationship Marketing:
  Jesse is clear that Levitate uses AI to enhance, not replace, personal connection. AI’s role is to help remember and scale personalized outreach, not to automate away authenticity.
  Quote:

  “My goal was always to allow our customers to scale their personal outreach, not to use AI to replace it ... People have a pretty good radar for automated communications.” — Jesse Lipson [09:03]
  “To take the kind of personal outreach that you could normally do with just your closest friends and family and extend that to hundreds of people in your network—I do think AI has that ability … but not to replace the personal connection.” — Jesse Lipson [09:03]

• Human + Machine Synergy:
  The focus is on using technology to help businesses remember key facts (birthdays, hobbies, etc.) to deepen relationships, reinforcing that tech should empower—not distance—human connection.

Notable Quotes & Memorable Moments

• “Keeping relationships at scale, that’s hard to do.” — Brian, Host [03:48]
• “First kind of resource that is critical is actually the human support ... We realized early on that if you just provide the software, that’s not necessarily enough ... it needs to be a software plus services approach.” — Jesse Lipson [07:06]
• “People have a pretty good radar for automated communications.” — Jesse Lipson [09:03]
• “Making them feel like you personally care goes so far in this business.” — Brian, Host [10:31]

Timestamps for Important Segments

• [02:19] — Jesse explains the gap in traditional marketing tools and the inspiration for Levitate.
• [04:34] — Discussion of healthcare’s unique relationship-driven nature and challenges with patient communications.
• [07:06] — The necessity of software + services and how Levitate supports small businesses beyond just software.
• [09:03] — The future of AI in relationship marketing and Levitate’s philosophy on technology’s role in personalization.

Conclusion

Jesse Lipson’s episode provides valuable, actionable insight into the evolving world of relationship marketing. Levitate’s model is tailored for authentic communication at scale—especially where personal connection forms the core of business success. The conversation emphasizes technology as a tool for empowerment rather than automation, with AI serving to bolster—not supplant—human relationships.

Listeners come away with an understanding of why relationship marketing matters, especially in sectors like healthcare, and how platforms like Levitate are positioned to help small businesses thrive in a tech-enabled, yet authentically personal, future.