Competitive Positioning: Learning from a Mayor's Upset Victory

Key takeaways

• Don't compete on the incumbent's terms. Change what credentials matter.

• Name the capability incumbents can't match and argue the market needs it right now.

• Safety is overrated as a buying criterion. Only 41% of hidden buyers rank the safest choice as a top factor, per Edelman and LinkedIn.

• Ground positioning in a story only you can tell. Authenticity is the structural advantage money can't buy.

In the startup world, founders face an impossible question every day. How do you compete when incumbents have more money, more brand recognition, and more proof points? Every pitch deck has to answer why anyone should bet on the newcomer when the safe choice already exists. In more than 16 years of B2B content marketing, I've watched that question stall more go-to-market strategies than any competitor ever did.

Mayor Webster Lincoln's path to leading East Palo Alto is that founder's journey translated to public service. A third-generation resident and a data scientist at Genentech, Lincoln ran against candidates with decades more political experience and deeper establishment connections. He didn't have the party machine. He didn't have the fundraising apparatus. What he had was a story nobody else could tell. On this episode of Magnetic, I asked him how he turned newcomer status into an advantage.

What is competitive positioning?

Competitive positioning is how you define the terms on which buyers compare you to alternatives. Strong challengers don't try to out-spend or out-credential incumbents. They change what credentials matter by making the case that the market's current challenges require a capability the incumbents can't match.

Don't compete on the incumbent's terms

The default assumption is that experience equals credibility. Incumbents lean on this constantly, in politics and in business. Their implicit message is always the same. We've been here longer, we know how this works, the risk is lower with us.

Mayor Lincoln's counter is something every B2B marketer should study. Instead of competing on the incumbent's terms and pretending to have experience he didn't have, he reframed the conversation entirely. He made the case that the city's challenges required a different kind of thinking, and that his background in data science and biotech research equipped him for that in a way traditional political experience wouldn't. You can see that analytical instinct throughout his data-driven storytelling.

Change what credentials matter

This is exactly what successful challenger brands do. They don't out-spend the incumbent. They don't out-credential them. They change what credentials matter. It's the same instinct Sharon Cordesse describes in her challenger brand strategy from Apple's underdog years, and it's the foundation of any SaaS content strategy built to compete with larger companies. If the market's scorecard favors the incumbent, your positioning strategy has to change the scorecard.

For marketing leaders at companies competing against larger, more established players, the lesson is strategic. Stop trying to look like the market leader. Identify the specific capability or perspective your incumbent competitors can't match, and make the case that the market needs exactly that capability right now. Then encode it in your positioning and messaging strategy so every asset repeats the reframe.

Why safe isn't the buyer's only criterion

The incumbent's biggest weapon is the perception of safety, and it's weaker than it looks. In Edelman and LinkedIn's 2025 B2B Thought Leadership Impact Report, only 41 percent of hidden buyers cited being the safest choice as a top factor when finalizing a decision, and 53 percent of decision makers said strong thought leadership makes brand recognition matter less. Buyers reward the vendor whose thinking fits the problem. That's the opening every challenger's thought leadership program exists to exploit.

Positioning grounded in a story only you can tell

Mayor Lincoln didn't just win a council seat with this approach. He was appointed mayor. His journey from outsider to city leader is a case study in how authentic positioning, grounded in a genuine personal story, can overcome every structural disadvantage. And the positioning kept working after the win, from his brand narrative strategy for the city itself to winning executive buy-in from a skeptical council. Borrowed positioning collapses under scrutiny. Authentic positioning compounds.

Watch the full conversation

Watch this clip if you've ever had to answer the question of why someone should bet on you instead of the proven option. Mayor Lincoln's answer will change how you think about competitive positioning.

If your positioning is losing to a bigger name's safety pitch, book 30 minutes with me and we'll rewrite the scorecard.

Frequently asked questions

What is competitive positioning?

Competitive positioning is how you define the terms on which buyers compare you to alternatives. Strong challengers don't try to out-spend or out-credential incumbents. They change what credentials matter by making the case that the market's current challenges require a capability the incumbents can't match.

How do you compete against a bigger, more established competitor?

Stop trying to look like the market leader. Identify the specific capability or perspective your incumbent competitors can't match, then make the case that the market needs exactly that capability right now. Ground the positioning in an authentic story only you can tell, because borrowed positioning collapses under scrutiny.

Does experience always win in B2B buying decisions?

No. Incumbents frame experience as lower risk, but Edelman and LinkedIn's research found only 41% of hidden buyers cite being the safest choice as a top factor in final decisions, and 53% say strong thought leadership makes brand recognition matter less. Buyers reward the vendor whose thinking fits the problem, not just the longest track record.