Why I Win Product Battles Against 'Better' Credentialed Leaders
The customer empathy advantage that most product managers never develop
The best product decision I ever made wasn't about AI, APIs, or architecture. It was spending three years in hotel conference rooms watching customers struggle with our "perfect" solutions. That field experience taught me something no PM bootcamp ever could: Empathy isn't a soft skill—it's a competitive weapon.
When I transitioned from technical services and pre-sales to product leadership at Akamai, I carried something most product managers don't have: the voice of frustrated customers in my head. Not the sanitized feedback from quarterly business reviews but the raw, unfiltered truth from the trenches. That voice became my north star through two major product transformations—one that grew from $180M to $220M at Akamai and another that achieved 5X growth from $13M to $65M at Arctic Wolf.
Here's what I learned: technical brilliance doesn't guarantee product success. But deep customer empathy? That's your secret weapon.
The Customer Voice in Your Head
Most product leaders get customer feedback through layers of translation. Sales says customers want feature X. Support says they're complaining about Y. Customer success reports satisfaction scores. But having lived in those hotel conference rooms, sitting across from frustrated CTOs trying to explain why our "elegant" solution didn't match their messy reality, I learned to hear what customers actually mean—not just what they say.
When a customer says, "We need better reporting," they're not asking for more charts. They're saying, "I can't explain to my boss why we bought this expensive tool." When they ask for "more integrations," they mean "your solution creates more work, not less." This isn't semantic nitpicking—it's the difference between building features and solving problems.
At Arctic Wolf, this distinction saved our entire product line. When I inherited a failing product with 18% churn, the engineering team was convinced we needed more advanced features and threat detection capabilities. Sales thought we needed better pricing and packaging. But when I spent my first 50 days conducting 23 customer interviews, I heard something different: "Though your technology does the job it is suppose to, it creates more work for our already overwhelmed security team."
The solution wasn't better detection—it was effective presentation of findings and continours monitoring that reduced their workload. That insight drove our pivot from vulnerability management towards attack surface management, which set us on a path of 5X growth.
Practical Application: Start every product planning cycle with unfiltered customer conversations. Not formal user research, but real talk with people who use your product daily. Ask them about their Monday mornings—what's the first thing that frustrates them about your solution?
Building Trust Across Functions
Field experience taught me something crucial about organizational dynamics: every function speaks a different language, but they're all trying to solve the same puzzle. Sales speaks revenue. Engineering speaks logic. Customer success speaks retention. Your job as a product leader isn't to pick sides—it's to be the translator.
When our Akamai sales team was struggling with a chaotic portfolio of 500+ SKUs, they weren't being lazy or stupid. They were drowning in complexity while trying to hit aggressive targets. When engineering resisted my rationalization plan, they weren't being stubborn—they were protecting code they'd worked hard to build. Understanding these perspectives isn't just nice leadership theory; it's a practical necessity.
The portfolio rationalization succeeded because I approached it as a translation problem, not a dictation. I showed sales how simplification would help them hit quota (clearer value props, easier demos, predictable pricing). I showed engineering how consolidation would reduce technical debt and let them focus on innovation instead of maintenance. Same strategy, different languages.
The result? Sales attach rates jumped from 33% to 49% in two quarters because every rep finally understood exactly what they were selling and why customers should buy it.
Practical Application: Before your next cross-functional meeting, write down each attendee's primary success metric. Then, translate your proposal into their language. Don't just explain what you want to build—explain how it helps them win.
The Translation Layer
Here's where field experience becomes indispensable: you learn to speak both technical and business fluently. Not just the words but the underlying concerns driving each conversation.
When a customer says they need "enterprise-grade security," the technical team hears compliance frameworks and encryption standards. Sales hears a price multiplier opportunity. But having sat in countless customer meetings, I learned that "enterprise-grade" usually means "something I can defend to my board if it breaks."
This translation ability proved crucial during my Arctic Wolf transformation. When I proposed pivoting from traditional vulnerability management to attack surface management, engineering worried about completely rebuilding our detection algorithms. Sales worried about explaining a new category to existing customers. Both valid concerns, but solvable once I translated the strategy into their terms.
For engineering: "We're not rebuilding everything—we're extending our existing capabilities to provide continuous visibility instead of point-in-time snapshots." For sales: "You're not selling a different product—you're selling the next evolution of what customers already value about us."
Practical Application: Create a "concern decoder" for your team. When someone raises an objection, pause and ask: "What's the underlying worry here?" Often, resistance isn't about your idea—it's about unaddressed fears you can actually solve.
Empathy as Competitive Advantage
The cybersecurity industry loves talking about technical differentiation—faster detection, better algorithms, and more comprehensive coverage. But after two decades in this space, I've learned that empathy often beats features in competitive deals.
At both Akamai and Arctic Wolf, our biggest competitors weren't other vendors—they were the status quo. Customers choosing to live with manual processes rather than adopt new tools. Why? Because most solutions prioritize technical elegance over human reality. They solve the problem as engineers understand it, not as customers experience it.
When we repositioned Arctic Wolf's offering around continuous monitoring rather than periodic assessments, we weren't just changing features—we were acknowledging that security teams are overwhelmed and understaffed. Our solution didn't just detect threats more effectively; it also reduced the cognitive load on already stressed professionals.
This empathy-driven positioning became our primary differentiator. While competitors focused on technical specs, we focused on making our customers' jobs easier. Result? We grew from a failing product to a $65M revenue stream with improving retention metrics.
Practical Application: Map your customer's emotional journey alongside their technical workflow. Where do they feel frustrated, overwhelmed, or unsupported? Those pain points are often bigger competitive differentiators than your latest algorithm improvement.
Your Empathy Action Plan
Ready to weaponize empathy in your own leadership? Start here:
This Week: Schedule three unstructured conversations with customers who use your product daily. Don't bring an agenda—just ask about their experience.
This Month: Create stakeholder empathy maps for every function you work with. What are their success metrics, fears, and constraints? Keep these visible during planning sessions.
This Quarter: Institute "customer voice" moments in your team meetings. Start each sprint planning or roadmap review with a real customer quote about their experience with your product.
The path from technical expert to product leader isn't just about learning new frameworks or methodologies. It's about developing the emotional intelligence to understand what people actually need—and then building solutions that serve those needs instead of your technical preferences.
Your customers don't care how elegant your architecture is. Your sales team doesn't care about your sophisticated algorithms. They care about solving problems and achieving goals. Empathy helps you see those problems clearly and build solutions that actually work in the messy reality where your customers live.
That's not just good leadership—it's a competitive advantage disguised as human decency. And in an industry obsessed with technical innovation, sometimes the most radical thing you can do is simply listen.