Leader to Know: Michael Sacca

A decade-old brand in marketing software is usually either a cash cow or a cautionary tale. Leadpages is neither. It has the trust and the customer base most startups would kill for, and it's sitting right in the path of the biggest shift in how marketing gets built since the web. That's why I said yes when Redbrick approached me to lead the next chapter in it's evolution.

Before Leadpages, I spent ten years hosting Rocketship.fm, one of the most popular independent startup podcasts. Hundreds of conversations with founders and CEOs shaped how I think about building companies. Every so often the show also opened a door I never expected, like one of the last interviews the piano great Galt MacDermot gave, on how the music industry had evolved and gave his career new, unexpected life, through sampling.

We decided early that AI was going to change how software gets built and that we'd rather be the ones doing the changing. The speed is exhilarating. What I'm proudest of, though, is that the team stayed resilient while every tool, workflow, and assumption about how we work was rewritten underneath them, and came out the other side shipping more than ever.

I coach my youngest son's soccer and football teams. A field full of kids who don't care what you do for a living is a good corrective for a CEO.

Most software gets worse the longer it exists. Every release adds something, nothing ever comes out, and ten years in you have a product nobody would design from scratch. Our job is to fight that. We have written rules for how Leadpages should feel to use, and every feature has to earn its place against them. That means as much time spent removing and simplifying as adding. Restraint is harder than shipping, and it's the reason we get to set the pace in our category instead of chasing it.

We look for high-agency people who need to win. I've found they're the most resilient and the most creative, and I think those things are connected. But needing to win is different from needing to be right. Needing to be right is a liability: it makes you defend bad ideas. Needing to win means you want to be the best, you're comfortable not being the best yet, and you'll experiment, be wrong, and keep improving until you get there. That's who we hire.

Slack, Roam, and Notion, like everyone else. The one that's changed how we work is Claude. It's not a tool the team uses so much as a colleague most of them talk to more than they talk to me.

AI generation as a feature. Every tool in our category now has a button that turns one sentence into a landing page, and almost none of what comes out is worth publishing. That's not because the models are bad. It's because writing the copy was never the hard part. Knowing what you're offering, who it's for, and what to leave off the page is the hard part, and a prompt box doesn't help with that. The winners in this space won't be the tools that generate the most. They'll be the ones that help people decide.

That a team of fifteen using AI seriously now beats a team of a hundred using it casually, and that most software companies are staffed for a world that ended about two years ago. People hear that and assume I mean cheaper. I mean better: faster decisions, fewer handoffs, no one whose job is coordinating the people doing the work. We're 15x more productive per engineer than we were a year ago, and I don't think we're special. I think we just stopped waiting for permission.

It's almost never the page. When something doesn't convert, people go straight to the headline, the button, the layout, and those things matter at the margin. But nine times out of ten the problem is upstream: the offer isn't clear enough that the visitor could explain it to a friend, or the person who landed there isn't the person the page was built for. A landing page can't fix a fuzzy offer or the wrong traffic. It can only make a good offer easier to say yes to. So before I'd touch the design, I'd ask two questions: what exactly are we asking for, and why would this specific person want it? If the answer takes more than a sentence, that's your conversion problem.

Because a feature is built to serve the platform, and a product is built to serve you. When a page builder is one tab inside a CRM or an email tool, its real job is to keep you in the ecosystem. Whether the page converts is somebody else's problem, and usually nobody's. That's why those builders all feel the same: good enough to check the box, never good enough to be the reason you win. Conversion is our entire business. If the page doesn't work, nothing else we do matters, and that pressure is the whole point. It's also why the AI moment favors focused tools. We could rebuild Leadpages from the ground up around what's possible now. A builder that's one line item on a platform roadmap is still waiting for its turn.

I'd push on the premise a bit. We're not a small business tool, we're a conversion tool, and plenty of our customers push enough paid traffic through Leadpages that testing is the reason they picked us. And small business doesn't mean low traffic; a local business spending a few thousand a month on ads can resolve a real test in weeks. The customers who can't test are the ones who don't have traffic yet, and that's a stage every business passes through, not a segment we've chosen. For that stage, the job of the feature is different. We don't want them declaring winners on forty visitors, so the product nudges them toward big changes over button colors and leans on what we've learned from millions of pages to give them strong defaults before they can generate their own signal. Testing is there for the day the ads start working. What matters is that they don't have to switch tools when it does.

The big shift, and the one that fits your thesis, is that the page has gotten smaller and the trust burden has gotten bigger.

Five years ago a landing page that converted was often still a sales letter: long scroll, stacked value props, countdown timer, a form asking for six fields. That format worked when people gave you the benefit of the doubt. They don't anymore. Visitors arrive from a phone, from an ad they half-read, already skeptical, and they decide in a few seconds whether the page feels like it was made by a real business or by a template. So the pages that convert now are shorter, do one thing, ask for less, and spend a larger share of their real estate on proof: real names, real faces, real numbers, and increasingly real video. The hype-heavy copy that used to lift conversion now depresses it, because everyone has learned what it signals.

A few other shifts underneath that. Mobile went from "make sure it works" to the primary design target, which forced the simplification on everyone whether they wanted it or not. The privacy changes (iOS 14, cookie deprecation, the slow death of cheap retargeting) made first-party data far more valuable, so the job of the page shifted from "close now" to "start a relationship you're allowed to continue," which favors low-friction asks: a booking link, a single field, a quiz, a text message. Message match got tighter because paid traffic got expensive; a page that opens with a different promise than the ad now wastes money you can feel. And the most recent one: AI made generic pages free, which means generic pages are now worthless. When anyone can generate a competent page in ten seconds, the only thing that converts is the thing that couldn't have been generated, which is specificity about this business, this offer, this customer.

For the piece:

"They got shorter and more honest. Five years ago the page that converted was still a sales letter: long scroll, a wall of benefits, a countdown timer, a form with six fields. That worked while people gave marketers the benefit of the doubt, and they've stopped. Today's visitor arrives on a phone from an ad they half-read, decides in three seconds whether you're a real business, and leaves if the page smells like a template. So the winners now do one thing, ask for as little as possible, and spend their space on proof instead of promises. Privacy changes pushed in the same direction: when retargeting got expensive, the page's job changed from closing the sale to earning permission to continue the conversation. And the last two years added a twist. AI made a competent page free, so a competent page is now worth nothing. The only thing that converts is what couldn't have been generated: the specific offer, for the specific person, with the specific proof that you're who you say you are.