Go Bold with Competition Like a Sybill PMM

Everyone knows the story of David and Goliath. A giant. Bigger, stronger, more experienced. And then the underdog who, on paper, has no business winning. But the part people forget is that David did not try to become a Goliath. He did not put on the armor. He did not try to outmatch the giant strength for strength. He found the one opening that actually mattered, then he went all in on it.

That part of the story feels very real when you are a PMM inside a startup. You look at the market leader and think, they have the brand, they have the budget, they have the default position in every deal, and you do not. So the question becomes, how can you win? That is what today’s episode is all about. We are talking about how a startup went head to head with a category leader and did not try to outspend them or out feature them. They got painfully clear on where the leader was weak and built an entire go to market motion around it.

I could not think of a better person to walk us through this than Collin Mayjack. Collin leads product marketing at Sybill, where he has been at the center of one of the hardest plays in B2B, competing directly with a category leader and turning it into real pipeline. Before Sybill, he was a product marketer at GoFundMe, working on a platform millions of people rely on during some of the most emotional and important moments of their lives. He has seen firsthand what it takes to build trust and drive adoption at scale. And what makes his background especially interesting is that before product marketing, he was a pastor. Long before he was building positioning and messaging, he was learning how to connect with people, earn trust, and move people through belief. Sounds pretty close to product marketing, if you ask me.

Step One: Get Clear on Differentiation

Collin’s first step is the one most teams rush past. Define what you do better than the incumbent, in a way that is specific and defensible. Not “we’re more modern.” Not “we’re easier to use.” The actual strengths where you win, and where the competitor is weak.

For Sybill, that meant leaning into areas where Gong users were already skeptical, like AI accuracy and the quality of insights. The point is not to throw shade for fun. The point is to give the market a clear reason to believe switching is worth it.

Step Two: Use Real Customer Frustrations

The next move is to stop guessing what people hate about the competitor and go find it. Collin talked about digging through forums, comment sections, and conversations with people who had switched. That is where the real language lives and where you find the complaints customers repeat without being prompted.

At Sybill, a lot of that frustration centered on Gong’s AI performance. Once you have that truth, you can build content that feels like it is saying the quiet part out loud. It lands because it is not manufactured. It is already being said.

Step Three: Build a Full Funnel Competitive System

Collin emphasized that bold competitive marketing only works when it is backed by substance. You need top of funnel content that grabs attention, but you also need bottom of funnel assets that prove the claim. Otherwise you get clicks, not conversions.

So the strategy becomes a system. Big, bold hooks that start the conversation, then evidence that carries it through the deal cycle. That includes proof points, product detail, and anything that helps a buyer justify the switch internally.

Put a Face on It

One of the most interesting parts of Collin’s approach is that he did not hide behind a company page. He used his personal LinkedIn to drive the narrative, share opinions, and engage directly with the market. That personal voice made the content feel more human and more credible.

It also created a clear association. People did not just remember “Sybill said this.” They remembered who said it, and they could respond to a person, not a brand logo. That is a big advantage when you are trying to build trust quickly.

Bold, But Not Reckless

Collin also talked about the guardrails. If you are going to go bold, you need litmus tests. Is it true? Can we back it up? Are we punching up in a way that is fair, or are we crossing into cheap shots? The goal is to be direct without being sloppy, and confident without being offensive.

That balance matters because competitive marketing can earn attention fast, but it can also backfire fast if it is not rooted in reality.

Messaging Critique: Zendesk

In our conversation, we also dissected a recent campaign by Zendesk, “Call Your Mom”. The campaign was meant to highlight AI agents over human customer support, but inadvertently trivialized personal audience sensitivities. Collin’s take was that you can still be bold without being careless. A more empathetic approach, like highlighting successful real world users and outcomes, can draw attention and create contrast without alienating the very people you are trying to win over.

Collin’s big lesson is that underdogs have a kind of freedom incumbents do not. You can take risks, be more direct, and challenge the default narrative. If you do it with clear differentiation, real customer truth, and a full funnel plan, you can actually shift perception and pull buyers into a new conversation.

If you are in a category dominated by a giant, remember this: you do not have to wait for permission to compete. You just need a strategy that is bold on the surface and solid underneath.

LINKS

Messaging Critique:

Zendesk: https://www.zendesk.com/

Zendesk Campaign Screenshot on Emily Fenech’s post: https://www.linkedin.com/posts/emilyelkins_say-it-with-me-who-approved-this-being-share-7455692957049090050-9OoD/?

Collin’s Sample Competitive Post: https://www.linkedin.com/posts/collinmayjack_edit-this-was-an-april-fools-joke-im-share-7445093042652385280-urzh/?

Connect with Collin:
LinkedIn: https://www.linkedin.com/in/collinmayjack/

Connect with Elle:
LinkedIn: https://www.linkedin.com/in/elle3izabeth/

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