Massimo Chieruzzi

I’ve always been kind of a geek. Starting with a Commodore 64 when I was 8, I haven’t spent a day without a computer since. I was an avid user of BBS before the internet and, except for a stint as a radio presenter for a grunge music program, I’ve always worked in tech.

Nonetheless, Creative Web grew into one of the best boutique web agencies in Italy. We focused on big projects for top brands that needed help both building robust, effective websites and launching and promoting them.

I started as a tech journalist covering the crazy dotCom boom in 2000 before launching my first company, Creative Web. But, beginning just few months before the bubble exploded, it had the worst timing.

Over the years, we helped many top brands succeed. We became eBay’s no. 1 developer in Europe and helped them launch their Real Estate vertical among other projects.
We built and managed the technological infrastructure for Facile.it, a car insurance price comparison Startup that recently sold for 400 million Euros.
We also helped Heinz relaunch their baby food brand online and double their traffic and signups in less than a year.

We grew to a team of 15 and won many awards. Along the way, I started speaking at many events about both web development and marketing topics.

While working as CEO of Creative Web, I started another company to pursue my love for journalism. Media Zen was a blog network, which I developed from zero to 500,000 visits per month in less than 3 months, mainly through SEO and Social Marketing.

This was in the early days of Facebook Advertising, which I started tinkering with.  The result was a huge increase in our fan base, accumulating hundreds of thousands of fans on our Facebook pages while spending less than $1,000.

While growing the Media Zen network, the idea for AdEspresso came to me, so I then quickly sold Media Zen making enough profit to fund my new venture.

In 2012, we started working on AdEspresso with a small team inside Creative Web. The goal was simple: help SMBs like us get the most out of their Facebook Advertising with an ads manager that was powerful but genuinely simple to use — and affordable.

In 2013 we were accepted into 500 Startups, so I moved to San Francisco to commit 100% to it. It worked: AdEspresso grew 10x in 2014 alone and went on to help tens of thousands of businesses run better Facebook Ads.

It was eventually acquired by Hootsuite, where I stayed for four years, until 2020, helping fold it into a much larger platform. Still the ride I’m proudest of.

In 2021 I got the startup itch again and co-founded Breadcrumbs, a lead-scoring tool. We got into Y Combinator — so yes, I’m a YC alum now. Honest take: Breadcrumbs never hit AdEspresso’s heights, but it was a great learning experience, and when we wrapped it up in 2025 we still managed a clean exit.

Today I’ve joined Treatwell as Chief AI Officer and board member. My mandate: drive AI adoption across our teams — technical and non-technical alike — and set the vision for how AI gets woven into our products. After more than two decades in tech, this is the most exciting shift I’ve seen — and I get to help a great company ride it.

Here are my main areas of expertise:

• AI Strategy & Adoption
• Applied AI / LLMs
• Startups & Product
• Growth & Inbound Marketing
• SEO/GEO & Content Marketing
• Lead Generation

And some things that I love:

• Alternative Rock (mainly Grunge)
• Good Food (hey, I’m Italian!)
• Automatic Watches
• Buying Kindle books that I’ll never have the time to read