When was the last time you felt overwhelmed trying to keep up with marketing trends, endless content demands, and rising costs?
If you’re like most business owners today, it’s probably an everyday battle. Creating valuable content takes time, and hiring it out can drain your budget fast. Meanwhile, new AI tools promise to save the day, but knowing where to start feels like one more thing to figure out.
That’s exactly why this episode of Endless Customers hit home. In this episode with Kyle Jepson, Principal Marketing Evangelist at HubSpot, we got right to the heart of how AI can save you time, money, and headaches—without losing the human touch buyers crave.
Kyle sat down with me live at IMPACT Live, bringing a wave of real-world insights and practical wisdom. No theory. No fluff. Just clear, actionable advice every business leader needs right now.
We explored:
- How to quickly create 18,000 words of authentic, helpful content in just a few hours (yes, really).
- Why community-driven learning is the secret weapon most businesses overlook.
- The smartest ways to start using AI without getting overwhelmed or losing control.
If you’re tired of chasing the next shiny marketing trend and ready for strategies that actually work, you’re in the right place.
Let’s dig in.
What does a HubSpot Evangelist actually do?
Kyle opened up about his one-of-a-kind role at HubSpot. “They created this job for me,” he laughed. Originally a HubSpot Academy professor, Kyle spent years creating in-depth certification courses that helped users master different aspects of the platform. But he began to notice something important: while comprehensive courses were great, most users needed faster, more practical insights they could apply immediately.
“Literally multiple new features released every business day,” Kyle said. “How am I supposed to stay on top of that?” And if he, someone who lives and breathes HubSpot, was feeling overwhelmed, what chance did everyday users have?
Instead of ignoring the problem, Kyle pivoted. He shifted from long-form courses to creating daily LinkedIn tips, quick videos, and short-form content designed to meet users exactly where they were. The goal was simple but powerful: Help people get more value from the tools they’re already paying for, without demanding huge time investments.
It wasn’t just about technical updates either. Kyle built a sense of community. Through webinars and social engagement, he created spaces where HubSpot super-users and admins could learn from each other, swap ideas, and feel seen. That’s where the magic really started to happen.
His story is a reminder that when you stay close to your audience’s real needs, opportunities appear. Entire career paths open. Sometimes faster than you think.
The power of community and accountability
We got into Kyle’s experience at IMPACT Live, and the passion in his voice was undeniable. “It’s three days of unbridled accountability,” he said. “You are going to hear all the things you could be doing better.”
But it wasn’t just the keynotes or structured sessions that left a mark. It was the atmosphere, the energy of being surrounded by people who weren’t there to just check a box. They were hungry. They were ready to transform their businesses and willing to put in the work.
“No one person or company has a monopoly on all the good ideas,” Kyle said, and he’s absolutely right. In an environment where everyone is committed to improvement, innovation naturally bubbles up. It’s the collisions of different experiences, challenges, and solutions that create real breakthroughs.
Kyle specifically called out the Endless Customers System™ (formerly They Ask, You Answer) and how Marcus Sheridan’s actionable frameworks provide the foundation, but it’s the community living those principles every day that makes the biggest difference. “Being surrounded by a community committed to living them? That’s next-level,” Kyle said.
It’s one thing to read about best practices. It’s another thing entirely to stand shoulder to shoulder with other business owners who are facing the same challenges you are, willing to be honest, vulnerable, and bold.
That’s where the real magic happens.
How to save time and create 18,000 words of content with AI tools
One of the most powerful moments in our conversation was Kyle’s story about helping a friend with her startup, Haven Music Lessons. Around a campfire one night, she shared her struggle: she had an army of talented teachers ready to offer music lessons, but barely anyone was finding her website.
Kyle’s wheels started turning.
“I have an idea,” he told her. They set up a lunch meeting, where Kyle came prepared with a full page of questions inspired by The Big 5 framework from Endless Customers. He recorded their conversation using nothing more than the microphone on his laptop. No fancy equipment. No big production.
From there, Kyle uploaded the audio to HubSpot’s Content Remix tools. The platform transcribed the conversation, and within minutes, Kyle was generating drafts of articles based on the information his friend had shared. In just a few rounds, he had 18 fully drafted articles totaling 18,000 words. Let that sink in: 18,000 words in less time than it takes to binge a Netflix series.
As Kyle put it, “This is a wildly fast speed.”
The results spoke for themselves. Within 48 hours of publishing the articles, Haven Music Lessons received five new inquiries. For a brand-new business, that was a huge win.
But Kyle didn’t stop there. He reflected on what could have made the results even better. “Making them findable is a good start,” he joked, noting that while the articles were live, the website navigation hadn’t been updated to direct visitors to all the new content.
The big takeaway? With the right questions, a basic recording setup, and smart use of AI tools, businesses can create an incredible volume of authentic, high-value content in a fraction of the time it would traditionally take. It’s like building a content factory in your backyard — without needing an army of writers or a massive budget.
Kyle’s experiment didn’t just save hours; it saved thousands of dollars in content creation costs. More importantly, it demonstrated that content rooted in genuine expertise and customer questions will always have staying power.
AI, Assignment Selling, and the next evolution of support
When we switched gears to HubSpot’s latest Spring Spotlight releases, Kyle’s excitement was contagious. While many people were buzzing about the AI-powered prospecting agents, Kyle’s eyes lit up when we got to the Knowledge Base Agent.
Here’s why it matters:
- The Knowledge Base Agent reads the real conversations your support team is already having—emails, support tickets, and recorded calls.
- It identifies the most common questions and recurring issues your customers are asking about.
- Then, it drafts full knowledge base articles based on real answers your team has already provided.
In Kyle’s words, “You just get this spiral up, a positive virtuous cycle.” Every time your chatbot or support portal encounters a question it couldn’t previously answer, the Knowledge Base Agent helps close that gap. Over time, your self-service support gets smarter, faster, and dramatically more helpful.
The beauty here? Your human agents spend less time answering the same repetitive questions and more time solving complex issues that actually need their expertise. That’s where the magic happens.
Kyle also painted a vision for the future: What if this same “listen and learn” approach applied to your sales team, too? Imagine an AI tool that monitors your discovery calls, sales emails, and negotiation conversations. It would spot the questions that come up again and again and recommend content you could create ahead of time to address them. Assignment Selling on autopilot.
It’s not science fiction. It’s closer than you think.
The bottom line? Whether it’s support or sales, smart use of AI is a massive time and money saver, and it creates a better, more seamless experience for your customers at every touchpoint.
Taking the first step with AI (without getting overwhelmed)
Toward the end of our conversation, Kyle offered some heartfelt advice for business owners feeling the pressure of “keeping up” with AI. If you’re feeling intimidated by all the shiny new tools and announcements, you’re not alone.
“Just find one simple place to start,” Kyle said. “You don’t have to try all the things at once.”
For Kyle, that first step meant something incredibly approachable: Switching his default search engine to Perplexity.ai instead of Google. A small, manageable shift that gave him firsthand experience with AI’s capabilities, without overhauling his entire daily routine.
The lesson is simple: You do not need to dive into AI headfirst to start benefiting. Instead of thinking about AI as a tidal wave you need to outrun, think of it like a current you can step into at your own pace. Start small, learn the flow, and let your comfort and expertise build naturally over time.
Trying to adopt every new AI tool at once would be overwhelming even for the most tech-savvy teams. But finding one place where AI could help you save time or gain clarity? That’s the smart move.
HubSpot’s AI approach: Thoughtful, not trend-chasing
Another thing that stood out in our talk was how Kyle described HubSpot’s philosophy around AI.
“We’re not just giving you AI tools and saying, ‘Good luck!'” he said. “We want it to be easy, fast, and safe to use.”
Unlike some companies that rush to slap AI onto every corner of their product just to say they have it, HubSpot takes a different approach. Kyle called it an “opinionated platform,” meaning HubSpot doesn’t just build tools for the sake of it. They carefully craft features designed to guide users toward smart, effective best practices.
AI is being layered thoughtfully into this philosophy. Every feature isn’t just about using AI; it’s about using AI well, in ways that actually improve customer experiences and business outcomes.
Kyle was honest, too. HubSpot may not have been the very first to market with flashy AI features. But from where we stand at IMPACT, that’s not a bad thing. Speed matters, sure. But so does usability, reliability, and making sure the tool actually solves real problems.
At the end of the day, it’s not about being first. It’s about doing it right.
And from everything we heard in this conversation, HubSpot is doing exactly that.
S0, what should you walk away with?
If you take just one thing from this episode, let it be this: The future of marketing, sales, and customer service is already happening. But you do not need to panic. You do not need to reinvent your entire business overnight.
Here is what you can do today:
- Focus on building trust through real, helpful content that answers your customers’ questions.
- Start experimenting with AI in small, approachable ways that fit your existing workflow.
- Stay plugged into communities like IMPACT that challenge you to think bigger, learn faster, and keep moving forward.
Kyle reminded us that sometimes a casual conversation around a campfire can spark huge leaps forward. It all comes down to asking the right questions, staying curious, and being willing to take that first small step.
That is the spirit of Endless Customers: Showing up, learning, sharing, and always pushing to get better.
Connect with Kyle Jepson
Kyle Jepson is a Principal Marketing Evangelist at HubSpot. He does his best to help the world keep up with HubSpot’s rapid pace of development. Prior to becoming HubSpot’s first evangelist, he was a HubSpot Academy Professor, where his educational videos garnered more than 2 million views annually.
