An AI Leadership Land Grab Is Happening. 5 Lessons for Every Startup.
This year half the billboards in SF promote AI startups at early (Series A/B) funding stages. What’s going on here is fascinating.
Welcome to Shawn, Brian, Amanda, Jeff, Nicky, Matthew and the 27 others who joined us this week. We’re glad you found us.
I spent the last 2 weeks studying AI wedges from CRM startups. At almost every turn were billboards.
Startups buying expensive San Francisco billboards is nothing new but it tends to happen much later in the growth journey.
HubSpot: 5 years after IPO
Monday.com: 2 years after IPO
Notion: 9 years and 20M users after founding
Slack: $5B valuation
This year half the billboards in SF promote AI startups at early (Series A/B) funding stages. Lightfield has fewer than 30 employees.
What’s going on here?
There are way more efficient ways to target tech executives and I don’t think it’s general brand advertising. What they are buying is actually far more interesting:
They're not selling to buyers. They're staking a claim as category leaders that's visible to every stakeholder: investors, customers, recruits, media and competitors.
Every emerging category has a 1- to 5-year window when the “leader” designation is up for grabs. “Which of these companies is going to be the company?”
The billboards that Attio, Lightfield and Clay are buying aren’t selling to buyers. They are attempting to plant their flags halfway through a 2-year AI challenger window that is quickly closing.
Here are five lessons every startup in an emerging category can take from this moment, whether you’re AI-native or not.
Lessons from the AI Land Grab
1. The land grab decides who makes the consolidation cut.
Four Waters Framework ends in Crowded Waters when the category eventually consolidates. The market doesn’t give oxygen to dozens of credible players forever. It promotes 1–2 incumbents (who acquired or shipped their way into a slot) and 1–2 challengers (who claimed a spot during the wave).
The land-grab moments determine who makes the cut.
The CRM category is reorienting around AI startups (Lightfield, Attio, Reevo) and incumbents with strong AI additions (Salesforce, HubSpot). In the next 12-18 months, the consideration set will settle on 3-4 finalists to recognize as leaders. The rest won’t disappear, but they won’t have a wind assist from the category, either. (Example: There’s OpenAI, Anthropic and everyone else.)
Many other SaaS categories are in a similar spot as challengers compete for those Leader slots.
Lesson: Categories consolidate. The land-grab window decides which challengers make the final cut.
Common misstep: Don’t default to looking at the competition as “startup vs incumbent” or “startup vs startup.” The finalists will likely include both.
2. The window is shorter than you think but varies by industry.
Different categories consolidate on different timelines. AI-native categories are uniquely compressed because the underlying tech is evolving rapidly and competitors can respond with new features in weeks.
I think the window for AI-native challengers claiming leadership spots in established categories is roughly 18–24 months from the wave’s start. Many challengers are already halfway through it.
Other industries take longer.
Recurrent provides EV battery analytics for the used car market. After we established our leadership claim, the auto industry took another 2 years to mature to the point where it wanted to recognize a leader. The full window was closer to 4 years.
Lesson: Each window is temporary, varies by industry and is generally shorter than you’d expect.
Common misstep: These leadership windows are not tied to you, your product or your funding stage. The category and market decide the timeline and set the consolidation clock.
3. Leader claims should look disproportionate to your stage.
Making a leadership claim may feel premature when you’re building with small teams and small revenues.
That shouldn’t stop you.
A claim that’s perfectly proportional to your stage is just a description. Planting your flag as a leader is a claim that will outpace the metrics. You’ll need to deliver on it later.
Lesson: A leadership claim may feel premature. The signal that you’re claiming is territory that nobody has fully earned… yet.
Common misstep: Don’t wait patiently to earn the recognition before making the claim. Your bold stance is what triggers the substance to catch up.
4. The judges who crown leaders vary by industry.
A leadership claim is only durable if (1) the judges see it then (2) begin to recognize it. But the field of judges varies by industry.
Enterprise SaaS: Placement on a Magic Quadrant matters more than any customer logo.
AI-native B2B: The stakeholder wall of customer logos and investors illustrates your momentum.
Automotive (from Recurrent): Traditional media and trade publications play an outsized role.
If you’re spending on signals visible to the wrong judges, you’re paying for impressions that don’t reinforce your claim.
Lesson: The right judges in your industry are a small set. Find them first then determine how to get in front of them.
Common misstep: Don’t default to whatever signals are loudest in other categories. What works in B2B SaaS is likely irrelevant in healthcare.
5. Claims need time to compound.
The substance of your claim takes time to compound until the industry is ready to award (or cede) the designation. That gap can be months or years.
But billboards alone don’t make a leader. There are startups with expensive signs along the 101 right now that won’t make the cut.
Progress comes from a stack of small signals: trade press mentions, new customer logos, conference panel slots, podcast appearances, original research, founder thought leadership. Individually, each is small. Together, they accumulate into a body of evidence for judges.
The job during this gap is remaining committed. Again. And again. And again.
Lesson: Patience is part of it. Compounding signals come from persistence + time.
Common misstep: Don’t mistake silence for failure. Keep beating the drum until the industry can hear it.
Planting the Flag Before Someone Else Does
People will tell you to let the product speak for itself. But this year thousands of amazing AI products will be passed then lapped by the leaders of their respective categories.
Attio, Lightfield and others are demonstrating how to invest now to make sure you’re one of the leaders at the front of the race.
Recently we covered growth loops to avoid ads. Land-grab signals aren’t ads. They’re claims to a status that determines whether your company makes the consolidation cut.
“How should we build brand awareness?” ❌
“What leadership claim made today then reinforced for the next 24 months keeps us in the consideration set?” ✅
These billboard ad buys aren’t reckless spending. They’re part of a race to claim a leadership spot before the window closes.
Find the signals and claim them so you’re ready for your category’s land-grab moment.
What are your challenges right now?
Hit reply to share the things you’re wrestling with in growth and marketing. If you’re stuck on something, someone else in this community probably just got unstuck from it.
The one thing I’d ask:
If the growth lesson today resonated with you, send it to one person or team that it could help. That’s who built this community, and that’s who belongs in it!
This is very timely for us. We thought we have time that we simply do not have. A great wake-up call! Thank you.