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Pain Points

Pain Points Content Preferences Decision Criteria Building Relationship Capital Outreach Tips Sales Process Preferences Customer Retention Goals and Motivations Positioning and Messaging Customer Research Buyers Journey Triggers to Evaluate Growth Mindset Brand Perceptions Barriers to Buy

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What Cybersecurity Leaders Must Learn from OT Practitioners in Underserved Critical Infrastructure

Despite being designated a critical infrastructure sector in 2020, the food and agriculture industry remains one of the most underserved domains in cybersecurity. Here's why and what you can do about it.

Dani Woolf

Pain PointsPain Points

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5 Mindset Shifts Security Teams Must Adopt to Master Multi-Cloud Security

Every time I talk to security leaders about multi-cloud, I hear the same frustrations. It’s complex. It’s overwhelming. It’s messy. But the real problem? It’s not just the technology - it’s how security teams think about it.

Dani Woolf

Pain PointsPain Points

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The CISO POV Checklist That Drives Buying Decisions

Most vendors treat the POV (Proof of Value) phase as a technical formality. A checklist. A box to tick on the path to contract signature. But that mindset is precisely what’s costing vendors the deal.

Dani Woolf

Pain PointsPain Points

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Why the Legacy Analyst Model is Misaligned with Cybersecurity Buyer and Vendor Needs

Legacy analyst firms aren’t disappearing, but...vendors are starting to re-evaluate their spending.

Dani Woolf

Pain PointsPain Points

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Why Cloud Security Starts with Applications—And How to Protect Them at Scale

Most security teams are still securing the cloud like they did their on-prem networks. It’s not working. Cloud security doesn’t start with firewalls. It starts with applications.

Dani Woolf

Pain PointsPain Points

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Why Mobile Security is Dangerously Overlooked (And What To Do About It)

MDM is not a security solution. It never was. It was never designed to be. Yet, for some reason, companies keep treating MDM as if it’s some kind of security blanket—as if deploying it means their mobile security problems are magically solved.

Dani Woolf

Pain PointsPain Points

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Why Human-Centric Security is the Next Frontier in Data Privacy (and Why It Matters Now More Than Ever)

Attackers are focusing less on breaking into systems and more on exploiting people. It’s no longer just about firewalls and zero-days. It’s about you.

Dani Woolf

Pain PointsPain Points

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The Hidden Cost of Demo Friction: Why the Software Sales Model Is Failing & How to Fix It

I’ve spent years in cybersecurity marketing and customer research and I can’t tell you how many times I’ve heard the same frustration from buyers: “Why is it so damn hard to try software?”

Dani Woolf

Pain PointsPain Points

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Why Business Information Security Officers Are Strategic Cybersecurity Translators

The Information Security Team can’t just be the department of ‘no.’ They have to understand the business needs and translate those into information security terms.

Dani Woolf

Pain PointsPain Points

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Risk Leadership Redefined: Why Chief Risk Officers Must Think Beyond Compliance

Amy Chaney, a seasoned risk officer, pulls no punches on cybersecurity leadership, toxic personal agendas, and why the cybersecurity industry's greatest risks—and solutions—start with people, not technology.

Dani Woolf

Pain PointsPain Points

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Why Malware Researchers Are More Than Just Analysts: Recognizing Their Strategic Role in Cybersecurity

The reality of malware research—the intense mental fortitude, the relentless strategic thinking—is often far less romantic and far more essential than we give it credit for. Here’s why.

Dani Woolf

Pain PointsPain Points

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Black Hat vs. RSA CISO Perceptions: Which Do They Prefer and Why?

Everybody's got to sell, everybody's got to buy things, but it's how the transaction is conducted that is important.

Dani Woolf