Tortoise and Hare Software

08/07/2026

A lot of MSP marketing plans are still built like Google is the whole internet.

Rank for the commercial terms.
Run the paid search campaigns.
Wait for buyers to raise their hands.

That used to be a cleaner playbook.

Now it’s too narrow.

You can be doing plenty right and still feel the ceiling. Your SEO might be stronger than it was two years ago. Your Google Ads might still bring in a good lead here and there. Your site might still show up for the obvious searches.

But the way buyers research has gotten messier.

They’re reading posts from people they trust. They’re getting warmed up through email. They’re asking AI tools weirdly specific questions. They’re comparing vendors quietly before they ever book a call.

So if your lead generation engine depends on a few Google rankings, you’re exposed.

Google still matters. It just can’t carry the whole strategy by itself.

You need to capture demand when people search, but you also need enough market presence that buyers recognize your point of view when they get there.

That means building around deeper buyer questions:

– blog content that answers sales conversations
– thought leadership that reaches people before they’re ready to search
– email that keeps your ideas in front of owned audiences
– long tail content that AI platforms can find and cite

Don’t throw away search.

Build around it.

Tortoise and Hare Software helps B2B tech companies turn SEO and Google Ads into part of a larger engine that includes content, distribution, social visibility, and stronger conversion paths.

We see this a lot with MSPs that already did the basic SEO work. The first wins came from fixing the website, targeting obvious keywords, and getting serious about Google Ads.

Then things slowed down because the market got harder to reach with search alone.

If your rankings still look fine but qualified leads have stalled, it may be time to build the rest of the engine.

Book a free consultation.

08/06/2026

If the first time a buyer notices your MSP is when they’re collecting proposals, you’re probably walking into someone else’s deal.

That’s the trap with demand capture only marketing.

You show up at decision time, but by then the water is already red.

The buyer has heard other names. They’ve asked peers for recommendations. They’ve read a few websites. They may already have a favorite, even if they’re still “exploring options.”

So now you’re not selling from a position of trust. You’re trying to win attention after the buying story has already started.

This is why competitive MSP deals feel so frustrating.

You get invited in. You have a decent discovery call. You send a thoughtful proposal. You follow up like you’re supposed to.

Then the buyer goes with the provider they already felt safest choosing.

It’s easy to blame pricing, timing, or the close. But a lot of these deals aren’t lost in the final conversation.

They’re lost months earlier, when your company wasn’t part of the buyer’s mental shortlist.

Demand capture reaches buyers who are already looking. Demand generation earns attention before they’re ready to look.

That difference is bigger than most MSPs think.

If a prospect has been seeing your thinking around reactive IT support, vendor switching, or business continuity, you’re no longer a cold option in a crowded comparison.

You’re familiar. You’ve already helped them make sense of the problem. You’ve already given them a reason to believe you understand what they’re dealing with.

The answer isn’t to fight harder once the buyer is already comparing five MSPs.

The better move is to stop waiting until decision time to become visible.

Tortoise and Hare Software helps MSPs build search driven demand generation around the problems buyers feel before they start vendor shopping, so you’re not depending only on people already deep in comparison mode.

Tired of entering the conversation after buyers already have a favorite?

Book a free consultation.

08/03/2026

If you look under the hood of a stalled MSP pipeline, the wiring problem usually isn't marketing. It's everything sitting underneath it. Ads and outbound only work as well as the foundation holding them up. Bad lighting on a sales call, no real CRM, no owned data list. These quietly cap what any campaign can do. In this solo episode, Brian Gillette walks through seven investments, each under $1,000, that build trust and confidence before a single pitch happens. None of it is more marketing spend. It's what marketing can't fix on its own. For MSP owners frustrated with their numbers and ready to look underneath the marketing. _____________________________________________________ Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format! It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg . . This episode is seven concrete, sub-$1,000 moves you can make this month.

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Tortoise and Hare partners with mid-market MSPs to help them increase lead volume, scale revenues, and make their businesses more attractive to prospective buyers when it comes time to sell.

Our marketing team tackles late-stage marketing problems that mid-market challengers face like multi-channel advertising campaigns, SEO, conversion rate optimization, performance reporting, and more.

Apply for a free MSP marketing consultation today.

If you look under the hood of a stalled MSP pipeline, the wiring problem usually isn't marketing. It's everything sitting underneath it. Ads and outbound only work as well as the foundation holding them up. Bad lighting on a sales call, no real CRM, no owned data list. These quietly cap what any cam...

08/03/2026

A flat MSP pipeline is not always a visibility problem. Sometimes it is a demand generation problem.

You can have a solid website, run ads, and show up when buyers search for IT support.

But if the only people hearing from you are already looking to switch providers, you are competing for a small slice of the market.

Demand generation is not simply posting more content.

It is the work of helping a prospect recognize a problem they have not fully named yet.

Maybe they have accepted reactive IT as normal. Maybe recurring technology issues feel like isolated frustrations. Maybe they do not realize their current provider is limiting growth, security, or employee productivity.

Your marketing should help them connect those dots.

It should give them a clearer way to think about the problem, show them what better IT leadership looks like, and make your MSP the company they associate with that better approach.

That is how you earn attention before someone searches for a replacement provider.

That does not mean leading every conversation with fear or complaints. It means teaching buyers how to see the cost of staying the same.

Do not wait until prospects are comparing MSPs to explain why they should care.

Create useful, opinionated content around the business problems your best clients are already experiencing. When the need to change becomes clear, your company is not an unfamiliar option. You are already part of how they understand the solution.

Ready to create demand before your next prospect starts shopping?

Book A Free Consultation.

07/28/2026

Repeat visitors don't come back to admire your homepage.

They come back because they're still deciding whether you're credible enough to contact.

If your MSP homepage doesn't quickly reinforce what you do, who you help, how it benefits them, and why they should trust you, that second visit can become another quiet missed opportunity.

This is where a lot of MSP marketing gets stuck.

You work hard to earn attention through referrals, SEO, Google Ads, email, partner conversations, and sales follow up.

Then a buyer comes back to the site before booking a call.

They're not looking for a scavenger hunt.

They want confidence:

You understand their problem.
You solve the specific thing they need.
Other companies have trusted you.
The next step is obvious and low friction.

If the homepage feels generic, thin on proof, visually flat, or hard to act on, it creates hesitation at the exact moment you need clarity.

A strong homepage isn't just a traffic destination.

It's a trust reinforcement page.

For repeat visitors, it should do five things well:

State exactly what you do in plain language.
Connect that service to the buyer's business outcome.
Show proof early and often.
Use the visual experience to guide attention, not decorate the page.
Make conversion easy from every major section.

That means logos, reviews, case studies, certifications, founder credibility, niche expertise, partner badges, and specific service proof shouldn't be hidden in one small section near the bottom.

The more expensive and risky the buying decision feels, the more reassurance the page has to provide.

This is where Tortoise and Hare Software helps MSPs and B2B technology companies tighten the connection between traffic, messaging, proof, design, and conversion.

Not just make the homepage look better.

Make it easier for the right buyer to understand you, trust you, and take the next step.

The best homepage experience feels obvious to the visitor because the hard strategic work has already been done behind the scenes.

We see this pattern often with B2B technology companies.

The homepage says some version of managed IT services, but the page doesn't show enough evidence that the company understands the buyer's world.

The design looks fine, but it doesn't guide attention.

The proof exists, but it's scattered across the site.

The CTA is there, but only after the visitor has already had to work too hard.

When those pieces are brought together, the homepage stops acting like a brochure and starts supporting more qualified conversations.

If repeat visitors are checking you out before they contact sales, what are they seeing when they come back?

Book a free consultation.

07/27/2026

Revenue can climb for a decade. Net worth can stay flat the whole time. That gap is where most MSP owners get stuck. Standard financial advice is built for salaried employees. Save a percentage, invest a percentage, wait for retirement. That breaks down when your income comes from a business and swings by six figures a year. Justin D Maxwell has worked one-on-one with close to 1,000 seven-figure earners on this problem. He joins Brian to unpack the difference between money and wealth, and how a family office model turns profit into a system instead of a guess. → Why money and wealth are not the same thing → How a scarcity number mindset keeps high earners stuck → The shift from comfort driven thinking to impact driven wealth → Using the Ansoff Matrix to decide: push your current market, or expand → Why partnering before buying lowers the risk of a new market → Applying poker's estimated value thinking to marketing decisions → The two mistakes that keep profitable owners from building real wealth This episode is for MSP owners making money that never turns into anything lasting. Justin lays out a deliberate way to turn profit into wealth. -------------------------------------------------------------------------------------------- Learn more about Adam via his website. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format! It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg . .

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Tortoise and Hare partners with mid-market MSPs to help them increase lead volume, scale revenues, and make their businesses more attractive to prospective buyers when it comes time to sell.

Our marketing team tackles late-stage marketing problems that mid-market challengers face like multi-channel advertising campaigns, SEO, conversion rate optimization, performance reporting, and more.

Apply for a free MSP marketing consultation today.

Revenue can climb for a decade.Net worth can stay flat the whole time.That gap is where most MSP owners get stuck. Standard financial advice is built for salaried employees. Save a percentage, invest a percentage, wait for retirement. That breaks down when your income comes from a business and swing...

07/27/2026

Your MSP homepage H1 isn’t just a headline anymore. It may become the sentence AI platforms use to describe your company.

That’s a problem if your above-the-fold messaging sounds like every other MSP site: “Reliable IT support.” “Managed IT services you can trust.” “Technology solutions for growing businesses.”

Those phrases may feel safe, but they don’t give buyers, search engines, or AI systems much to work with. As AI search becomes part of how prospects research vendors, your homepage messaging has to do more than look clean. It needs to make your positioning obvious: who you serve, what problem you solve, what kind of buyer you’re best fit for, and what makes your approach different enough to remember.

If that clarity isn’t visible above the fold, you’re making buyers and machines infer your value from generic copy.

A stronger MSP homepage H1 should be specific enough that someone could repeat it after one glance. Not clever. Not stuffed with keywords. Not vague “IT solutions” language. Clear positioning, written for humans, but structured enough that AI systems can understand what your company should be associated with.

This is why homepage messaging matters more in 2026 than many MSPs realize. Your website isn’t only a conversion asset anymore. It’s also a positioning source for the systems buyers increasingly use to summarize, compare, and shortlist vendors.

If your MSP homepage still sounds like it could belong to five competitors, it’s worth tightening before AI search turns that vagueness into your public positioning.

Tortoise and Hare Software helps B2B technology companies sharpen search-driven messaging and turn qualified attention into better-fit leads.

Book a free consultation.

07/24/2026

Referrals are great until your MSP starts waiting on them.

They feel dependable because they come with trust already attached. A client introduces you. A partner remembers your name. A warm conversation turns into a decent deal.

That works for a while.

Then growth starts asking for more than your current network can consistently provide.

You’re still doing good work, but the calendar depends too much on who happens to make an introduction this month. That’s a risky place to be when you’re trying to move from the low millions into the next stage of ARR.

The problem isn’t referrals.

The problem is making referrals carry the whole growth plan.

Search gives your MSP a bottom-of-funnel layer that reaches the next closest thing to referrals: in-market buyers who already know they need help.

They may be comparing managed IT providers. They may be worried about cybersecurity. They may need compliance support, Microsoft help, or a better provider than the one they have now.

They don’t know your clients. They aren’t waiting for a warm intro. But they’re actively looking for a company they can trust.

That’s where search driven demand generation helps.

– Clear service pages that match the problems buyers are searching for
– Local and vertical visibility when they start comparing options
– Conversion paths that make the next step easy
– Paid search that shows up when buying intent is already there

Tortoise and Hare Software helps MSPs turn those pieces into a focused system instead of a scattered list of marketing tasks.

We see this often with MSPs that grew through strong relationships. Referrals helped them build momentum, but eventually stopped giving them enough consistency for the next stage of growth.

Keep the trust that comes from referrals. Add the bottom-of-funnel search layer that helps in-market buyers discover you before an introduction ever happens.

Ready to make growth less dependent on who remembers your name this month?

Book a free consultation.

07/22/2026

Most MSP campaigns start in the wrong place.

They start with the service menu.

Managed IT. Cybersecurity. Cloud support. Compliance help.

Those are important, but they’re not usually what makes a buyer act now.

Something happened first.

An audit is coming up.
The internal IT hire didn’t work out.
Support tickets are stacking up.
A cybersecurity scare made leadership nervous.
The current provider dropped the ball again.

That’s the moment your campaign needs to meet.

Better search campaigns are built around buying triggers, not just service categories.

A service category tells you what the buyer might need.

A buying trigger tells you why they’re looking now.

That difference should shape your keywords, ads, landing page copy, and offer.

Someone replacing a bad vendor doesn’t need a generic list of services. They need to see that you understand the frustration, the risk, and the cost of letting the problem drag on.

The same service can speak to very different situations.

A company preparing for a compliance deadline needs a different message than one dealing with constant outages or a leadership team that’s lost confidence in internal IT.

A useful starting question is:

“What happened inside this company that would make them look for help today?”

That question leads to sharper campaigns than “Which service should we promote?”

Tortoise and Hare Software helps B2B tech companies connect search strategy, messaging, and conversion pages to the moments that create better sales conversations.

Want campaigns that speak to what makes your buyers act now?

Book a free consultation.

07/22/2026

Your best buyer might not be searching for “managed IT services” yet.

They might be searching the headache first.

“Why does our remote team keep losing access?”

“What happens if we fail a compliance audit?”

“Why does employee onboarding take forever?”

That’s the part many MSP search strategies miss.

Most MSP websites are built around service names because that’s what the business sells: managed IT, cybersecurity, cloud support, compliance, help desk.

That makes sense once the buyer knows what they need.

But many buyers don’t start there.

They start with downtime, insurance pressure, failed audits, slow onboarding, recurring tickets, and frustrated employees.

Before they compare providers, they’re trying to understand what’s wrong, how serious it is, and what kind of help they may need.

A stronger search strategy follows that path:

symptom

risk

solution category

provider shortlist

If your content only shows up at the shortlist stage, someone else may have already helped the buyer frame the problem.

Someone else may have explained the risk.

Someone else may have shaped what they believe a good solution should include.

This doesn’t mean chasing random informational traffic.

It means writing around the problems your best buyers already recognize.

The right content helps them connect the dots from “this is annoying” to “this is a business risk” to “we need a better IT partner.”

Tortoise and Hare Software helps B2B tech companies find those earlier search opportunities and turn them into content that attracts more qualified leads, not just more visitors.

We see this often with MSP websites.

The service pages are there. The keywords make sense. The site looks complete.

But the content skips the questions buyers ask before they know the right service name.

Want your search strategy to show up before buyers have already built their shortlist?

Book a free consultation.