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Kendra Lee on AI, Sales ROI & MSP Growth Strategy

Kendra Lee: Authentic Sales, Real ROI, and the AI Reset Moment

Something’s happening in the channel right now; if you’re paying attention, you can feel it. 

I recently had the privilege of sitting down with Kendra Lee again for Sunny Silver Linings, and as always, the conversation left me reflecting on just how much the MSP space is evolving, and how fast. Kendra’s not just a respected sales strategist or a top-tier HubSpot Gold Partner. She’s one of those rare people who can take something as complex as AI-powered sales and make it feel clear, human, and actionable. 

This time around, our conversation felt different: Deeper. Maybe it’s because I recently hit my own “reset moment” turning 50: a milestone that made me reflect on the first two quarters of my life and the next two to come. Or maybe it’s because we’re all living in a time when the rules are changing. AI is no longer a buzzword; it’s become the backbone of how we rethink sales, marketing, teamwork, everything. 

From Guesswork to ROI: Where AI Hits Hardest 

I asked Kendra a straight-up question: Where does AI have the biggest impact in MSP sales? Without missing a beat, she answered: prospecting and follow-up. Two places that nearly every MSP sales team struggles with, no matter how mature they are. 

And here’s the reality check: Salespeople fall short not because they’re lazy, but because they don’t have the time, consistency, or sometimes the right tools. Kendra broke it down beautifully: AI can now generate customized email sequences, LinkedIn outreach, call scripts, and even entire messaging frameworks tailored to your target market. And once you’ve done your homework on a prospect, it can personalize even further. 

This is transformational. Because now your team doesn’t have to guess. They can show up prepared, confident, and consistent. 

Analysis That Drives Real Action 

But she didn’t stop there. What blew me away was the next-level opportunity: analysis. AI can now help MSPs review campaign performance, track conversion rates, test messaging, and uncover what’s actually moving the needle. 

Are your emails converting better than your LinkedIn DMs? Are certain industries responding more than others? How many touchpoints does it take to get a response? These aren’t just data points; they’re insights that fuel ROI. 

I love how Kendra framed it: AI gives you the power to adjust and improve in real time. And that’s where the true value lies. Not in doing more, but in doing what works: better. 

Authenticity Still Wins 

Of course, I had to ask about authenticity. Because we’ve all seen what happens when AI is used poorly: generic content, lifeless copy, messaging that “smells” like it was written by a bot. 

Kendra had a great take: The key isn’t just using AI; it’s training it. You have to embed your company’s voice, your personal tone, and your brand guidelines into every prompt. AI doesn’t replace your voice; it amplifies it if you do it right. 

She shared that she’s writing her third book right now (yes, third!) and even in that process, it’s about guiding the AI to reflect her thought leadership: consultative, human, light-hearted, not salesy. That’s what MSPs need to remember: AI is your assistant, not your identity. 

Relationships Still Matter, Maybe More Than Ever 

We also touched on something close to my heart: relationships. As powerful as AI is, people still buy from people they trust. Tools like AI, Seamless.AI, ZoomInfo, or even Perplexity (which we use internally before QBRs and meetings) are there to help us know more about the people we’re connecting with. But it’s up to us to use that insight to create real connections. 

Kendra nailed it: use AI to create space for more meaningful conversations, more valuable business reviews, and deeper partnerships. 

Predictable Sales, Powered by Data 

When it comes to scaling, predictability is everything. Kendra emphasized that the secret is discipline in data. If your reps aren’t updating your CRM consistently, your AI insights are flawed from the start. No data, no direction. 

Her recommendation? Use AI inside your CRM, like HubSpot, to build dashboards, analyze patterns, and surface opportunities. And if your CRM doesn’t do that, extract the data and run it through AI tools that can. Because sales consistency = sales growth.  

What Not to Do with AI 

We ended with a question I hear constantly at my Mastermind events: What should MSPs avoid when diving into AI? 

Kendra’s advice was gold: Just because you can, doesn’t mean you should. 

Don’t get caught up trying to do everything yourself; especially in areas where you’re not strong. Focus on your zone of genius and find the right “who’s” to handle the rest. I immediately thought of my own coach Dan Sullivan’s philosophy: Who, not how. It’s a mindset shift from doing to leading. 

Final Takeaways 

As we wrapped up, I asked Kendra to distill it all into three actions MSPs can take right now: 

  1. Get consistent. Use AI to standardize your follow-up emails, messaging, and sales playbooks. 
  2. Analyze your pipeline. Let AI tell you what it sees, then listen. 
  3. Take action. Start with one thing. Don’t wait for perfect. 

This conversation reminded me again why I love this community. The MSP space is full of people who genuinely want to grow, support each other, and lead with heart. And leaders like Kendra are helping us all rise together, with strategy, authenticity, and a little AI superpower. 

For more content like this, be sure to follow IT By Design on LinkedIn and YouTube, check out our on-demand learning platform, Build IT University, and be sure to register for Build IT LIVE, our 3-day education focused conference, August 4-6, 2025 in Jersey City, NJ!

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