Jennifer Bleam on turning AI buzz into billable revenue
Sales Sherpa Jennifer Bleam has worked with nearly 2,000 MSPs. She breaks down how to package and sell AI services and turn efficiency into recurring revenue.
Sales Sherpa Jennifer Bleam on turning AI buzz into billable revenue
Everyone's talking about AI. Your clients are asking about it. Your vendors are pitching it. Your technicians are either experimenting with it or worried it'll replace them. But here's the question almost no one in the MSP space has figured out: How do you actually make money from it?
Jennifer Bleam, the founder of MSP Sales Revolution, has worked with nearly 2,000 IT companies, and she's watched this movie before. Five years ago, it was cybersecurity that was a massive opportunity that separated the proactive MSPs from the pack. Today, it's AI, and she believes the opportunity is even bigger. The difference? This time, clients are coming to you first.
Known fondly as the Sales Sherpa, Bleam started her career helping MSPs sell cybersecurity. When she realized her "natural" sales ability was actually a rare skill, she built a business around guiding MSPs through the terrain of positioning, sales systems, and revenue growth. Now, as AI reshapes the industry, she's helping MSPs do what they've always struggled with: turning internal efficiency gains into external, chargeable value.
In this conversation, Bleam breaks down which AI services are easiest to package and sell, how to structure AI conversations so they don't devolve into chaos, and why starting small with what she calls an "AI Domino" is the key to building client trust and unlocking recurring revenue. If you've been wondering how to move from AI experimentation to AI monetization, consider this your guide.
How do you see AI reshaping the way MSPs scale and generate revenue?
Just like MSPs were able to lead with cybersecurity 5-6 years ago and that gave them a massive advantage as a differentiator, AI is now able to provide that same disruption. MSPs will be able to add a new revenue line item via workflow optimization and access to even larger companies who want to embrace AI.
How can MSPs make AI a lever not just for efficiency, but for unlocking new revenue streams?
MSPs are doing some amazing things inside their service departments, including with tools like SuperOps with AI agents connecting to knowledge base articles, triaging low-level tickets, that kind of thing. But I get really excited when I work with MSPs that are starting to monetize AI, because this is a tremendous opportunity. I'd wager it's a bigger opportunity than cybersecurity was five years ago.
Here's why: The US Chamber of Commerce released a paper in August 2024 that stated 96% of small business owners were planning to invest in AI and other forward-leaning technology in 2025. That is an unprecedented number. Even at its height, cybersecurity was never something clients would seek after. It was always the MSPs convincing clients why they needed it.
This current trend with AI is so very powerful psychologically because of the buzz in the market. It's creating external pressure on small businesses and they are clamoring to adopt it—they just don't know how.
Which AI-enabled services are the easiest for MSPs to package, position, and actually sell profitably?
The easiest AI-enabled service for MSPs to package and sell profitably is a Virtual AI Officer offering—what I call a VAO. It fits naturally into what MSPs already do. Think of it as the AI version of a vCISO or a structured QBR process, just focused on workflows, efficiency, and business outcomes.
Because the model is familiar, MSPs can position it confidently, price it sustainably, and deliver meaningful value without needing deep technical AI expertise. It's highly scalable and extremely profitable.
How can MSPs integrate AI into a structured sales or service system rather than just treating it like another shiny tool?
MSPs can avoid "AI chaos" by treating every AI conversation like a critical path rather than a tech discussion. When a client says, "We want to use AI," you respond with, "What are you trying to accomplish?"
Their answer will almost always fall into one of three buckets: doing the same tasks more efficiently, adding new capabilities, or simply not knowing how to use AI but wanting to "do something." Once you map those three paths and prepare your typical responses, AI stops being a shiny object and becomes a structured, repeatable system inside your sales and service process.
Can you share examples where AI has helped MSPs improve their win rates, close deals faster, or make sales conversations more compelling?
MSPs should price AI services based on the business outcome they create, not the technical feature they deliver. Nothing illustrates this better than a recent discovery call where an MSP I coached uncovered nearly 40 AI opportunities.
One of those was a simple connector between two software tools that would eliminate the need for two additional full-time hires as the company scaled—saving over $80,000 per year in real costs, plus significant efficiency gains. When MSPs anchor pricing to those kinds of real, measurable outcomes, their win rates increase immediately because clients can see the ROI before the project even begins.
What should vendors be doing differently while bringing AI solutions to the MSP market?
Vendors often miss the mark by rushing to showcase their AI features instead of clearly articulating the business problems those features solve. MSPs demo and purchase based on the promise of a better, more efficient future for their clients, and vendors who paint that picture instantly stand out.
The vendors who win will be the ones who lead with outcomes, not tools, and help MSPs envision the "rosy future" their solution enables.
AI can increase operational efficiency, but not all MSPs know how to monetize that efficiency. What's your advice on turning internal gains into chargeable value?
Using AI internally to boost efficiency doesn't automatically translate into a sellable service, and that's okay. The real value of internal AI wins is that they give MSPs firsthand experience, real stories, and the confidence to speak about AI credibly with clients.
Once an MSP builds its own automations, agents, or connectors—and wrestles with the various challenges—it becomes far easier to identify similar opportunities in a client's environment. To put it another way: internal implementation is the training ground, and monetization comes from applying those same principles to solve business problems for clients.
Technicians fear AI replacing them. From a leadership and scaling standpoint, how should MSP owners reframe this internally?
Technicians have survived every wave of automation because their value isn't in the task—it's in the thinking. MSP owners should reinforce that AI is simply the next layer of tooling, just like RMM, scripting, and remote support were in prior decades.
And we've all seen AI fail—whether it's writing garbage code or writing an SOP that's way too overengineered and complicated for a human to use. This reinforces that AI, at least today, only augments thinking. It doesn't replace it.
How can MSPs leverage AI to improve lead generation consistency?
MSPs can use AI to generate more consistent leads by automating the activities that typically fall through the cracks: engaging website visitors with a chatbot, follow-up sequences, nurturing old prospects in their CRM. AI also enables MSPs to show up more consistently with content, insights, and industry-specific resources, which keeps them top of mind and drives inbound conversations.
And with smart chatbots and automated outreach, MSPs convert more passive interest into live meetings without adding workload to their sales team.
What categories of AI tools do you believe will have the biggest impact on MSP sales and profitability over the next 12–24 months?
24 months is a LOOOONG time with AI, so let me focus on the six-to-twelve-month window.
The biggest impact will come from AI tools that help MSPs sell more - research assistants, script generators, on-demand proposal or slide-deck creators that make every sales conversation sharper and more consultative. Right behind that, or maybe even tied for first place, will be AI tools that enhance client value: readiness assessments, automated insights, roadmap generators. These create differentiation, stickiness, and higher-margin advisory revenue.
And finally, AI-driven marketing tools will be transformational, especially for MSPs who struggle with content. Daily LinkedIn posts, video scripts, even digital-twin video creation—these will allow MSPs to show up consistently in front of prospects without adding much workload.
Trust is everything in sales. How can MSPs build trust with clients when rolling out AI-powered services or automations?
MSPs build trust by starting small and proving value quickly. I teach clients to use the Eisenhower Matrix and choose an easy-to-execute, high-impact automation or AI service that's simple for the end user to adopt. When the first AI win feels effortless and has a business impact, trust accelerates and clients lean in for the next phase.
I call this first project the AI Domino. Once that first project is completed, it naturally leads to the next one.
For MSPs preparing for acquisition or trying to boost valuation, where does AI sit in the conversation today?
It's still far too early to make definitive claims about AI boosting MSP valuations, and it's not an area I consider myself an expert in. What I can say is that acquirers are watching AI closely, and M&A firms love MSPs who think in systems and processes.
This seems to suggest that an MSP who sells AI well, because they think in flowcharts and logic, will be more appealing to the marketplace. But we're too early for there to be any data on this topic.
If an MSP owner came to you today and said, "I want AI to become a real revenue stream," what's the first step you'd have them take?
Start by packaging one simple, outcomes-focused offer so clients have something concrete to buy. Then validate it through a handful of real conversations to see what resonates, and refine it before scaling.
Momentum comes from clarity, not complexity.
Beyond the Sherpa: Jennifer Bleam Unplugged Jennifer Bleam will tell you she's a workaholic who struggles with work-life balance. She'll admit she listens to business podcasts while doing diamond art painting, because apparently even her hobbies need a productivity soundtrack. But here's what she won't tell you: for someone who claims balance doesn't come naturally, she's built a remarkably intentional life. She keeps her workday to 8:00-5:30, limits evening work to twice a week, and (imperfectly, she'd say) takes one Friday off each month. That's not a workaholic. That's a woman leader who's figured out how to pour into others without running herself dry. And it's exactly why MSPs trust her to guide them to the summit. The Sales Sherpa Origin Story The nickname started as "Cybersecurity Sherpa" when Jennifer first helped MSPs sell cybersecurity. Working through the StoryBrand framework, the analogy of "climbing a mountain alone" resonated deeply. As her work expanded beyond cyber into sales, mindset, positioning, and now AI, the nickname naturally evolved. The common thread? "MSPs don't need someone to walk the path for them; they need someone who has climbed it before and can walk with them and guide them safely to the summit." Her breakthrough came early in her entrepreneurial journey during an intensive week-long sales training. She was consistently the top seller in the room, and people kept asking how she achieved her results, something she'd never recognized as a unique strength. That moment crystallized an odd truth: what felt natural to her was incredibly difficult for most people. Navigating a Male-Dominated Space One of Jennifer's biggest challenges has been imposter syndrome, walking into highly technical, male-dominated rooms and feeling like she had to prove herself twice: once for her expertise, and again for her right to be heard. Being interrupted mid-sentence is another ongoing challenge, something many women experience but rarely talk about because it's so discouraging. These days, when it happens, she lets the person finish and then calmly but firmly says: "You just interrupted me. If you want my perspective, you'll need to let me finish, or I'm happy to leave." The tone shifts immediately. "At some point I realized: I can't control people, but I can control how they treat me." On Women in Sales Jennifer wishes one stereotype would disappear for good: that women are "pushovers" or somehow less capable in sales. "The data would argue with you," she says. "Women consistently outperform men in sales roles." She attributes this to empathy, the ability to listen deeply, and the way women help prospects feel comfortable opening up. "The qualities some people perceive as 'soft' are often the exact qualities that close the biggest deals." As AI forces MSPs to shift from pure technical work to workflow design and advisory, Jennifer believes women's strengths will become even more critical. "AI adoption isn't just a technical decision; it's often an emotional one. Clients don't buy AI tools. They buy business impact, and that only happens when they feel understood." Her Advice to Women in Tech Two words: trust yourself. "Too many women don't discover their strength, intuition, and leadership voice until their 40s or 50s," she says. "I wish I could give every woman in her 20s or 30s the gift of seeing herself as the rock star she already is." Her message is unequivocal: "Lean into your abilities, own your brilliance unapologetically, and stop waiting for someone else to validate your worth. You're amazing; you are one of a kind; and the world needs you. So step into your greatness and shine." |