Jennifer Oladipo's Blog Posts

Professionals in a conference room shaking hands
By Jennifer Oladipo / Apr 16, 2026

Budget Allocation: Where Cybersecurity Pitches Go to Die

The vast majority of cyber deals die at the budget allocation, says Adam Anderson, co-founder of Threat Captain, a cybersecurity sales enablement platform. They fail because somewhere between the IT person who understood everything and the CFO who controls the checkbook, your message got lost in translation. But those checkbooks are open.
Man presenting data to clients
By Jennifer Oladipo / Mar 26, 2026

5 Strategies for Risk Reports that Make Clients Move

You spent hours scanning networks, compiling data and building a comprehensive risk assessment. You present it to your client. They nod politely, say "thanks," and then ... nothing. No urgency. No budget conversation. Just a PDF collecting digital dust in their inbox. They’re letting you know they don’t care, and it’s up to you to change that, says Cytracom COO, John Tippett.
Image of graphs and financial research on laptop screen
By Jennifer Oladipo / Feb 24, 2026

Digging Beats Pitching: Win Business with Customer Financial Insights

If you're leading client meetings diving straight into the technical weeds, you're probably losing..

By Jennifer Oladipo / Feb 4, 2026

The MSP Owner's Roadmap to Operational Sanity

Amanda Doucette-Lachapelle was digging through her documentation system when she found 11 different..

By Jennifer Oladipo / Jan 29, 2026

Your Flight Plan for Thriving in 2026

What does it take for an ITSP to thrive in the New Year? If you listen to vendors, it's XDR,..

See Around Corners with Customer Financial Insights

Most IT service providers (ITSPs) wait until invoices go unpaid to realize a client has cash flow..

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Ditch These vCIO Mistakes to Build a Program That Actually Works

Your clients still see you as a help desk. Not as a strategic partner. Not as a trusted advisor...

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5 Tricky M&A Truths Nobody Talks About

You can believe the headlines about MSP acquisitions making a comeback. After M&A activity fell..

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The Reason Your ITSP Partners Might Be Ignoring You

Maybe you’ve seen this before. The partner campaign looks perfect on paper. Sharp messaging, clear..

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A Three-Phase Approach for Social Media Success

In today’s digital landscape MSPs are discovering that social media isn't just for B2C..

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Mastering Managed Services by Thinking Beyond Technology

Running a successful MSP business requires navigating far more than technical challenges.

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Slow Down to Speed Up: The Power of Context in Leadership

When inbox notifications are piling up and projects don’t feel like they’re moving fast enough,..

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Launch Your First AI-Powered Marketing Campaign: A Complete Checklist

Marketing doesn’t have to be your Achilles’ heel. While many MSP marketers and leaders struggle to..

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Why Being Yourself (Thoughtfully) is Good Business

In today's business world, the line between personal and professional identity is increasingly..

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6 AI Myths MSPs Can’t Afford to Believe

The hype around artificial intelligence (AI) has many MSPs wondering whether—and when—to dive in...

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Breaking Barriers: How We Can All Do Better

Even as their numbers rise, women still often face outdated stereotypes and biases that create..

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CIRCIA and MSPs: Navigating the New Era of Cyber Incident Reporting

The cybersecurity landscape is shifting beneath our feet, and MSPs are caught in the middle of a..

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Standing at the Data Crossroads: Simplify, Organize and Act on What Matters

For MSP business owners, dealing with data is like standing at a busy intersection with traffic..

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Designing a Business Strategy for Today’s Competitive Landscape

Solid business strategy will always be important in the ever-evolving market, but today’s..

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If You're Not Using MDF, You're Leaving Money on the Table

This is the quarter to create a strategy to use thousands of dollars in Market Development Funds..

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