Caleb joined Madrona as Head of Marketing in 2025.

Journey to Madrona

A Bay Area native, Caleb built his first PC in middle school and was coding well before he could drive. He’s always felt at home in the fast-paced world of startups and has spent nearly 20 years on every side of the table. Notable stops along the way include: the founding marketer of martech startup Accomplice, the chief strategy officer of award-winning brand agency Free Range, and VP of digital strategy at Tech PR Agency of the Year, Mission North. Then, in 2020, he joined Unusual Ventures as VP of marketing.

He joined Madrona to help extend the story of Madrona’s investors and founders in the new media era. And to do so with an AI-native lens, reimagining every marketing touchpoint and service we provide to help our founders win.

Lessons Learned

1. Audience first, always. It’s not about what you say, it’s what your audience hears. The best marketing starts with a clear-eyed view of who you’re talking to and what matters to them. Work backward from there, and you will find the common ground for a durable relationship.
2. Curiosity gets you everywhere. One of the best things about the fast-paced world of startups and technology is that there’s always more to learn. This is vital for the craft of marketing because strategic playbooks often grow stale over time, and the only way to keep winning is to keep challenging what you think you know.
3. Speed is a superpower. Related to the value of curiosity, the real world is the ultimate teacher, and the ability to ship quickly gives you more opportunities to learn what works. Speed propels feedback loops that expand your surface area for learning and thus success. The team that compresses time learns more, and the team that learns more wins.

When he’s not in the office…

Caleb is a former NCAA athlete and an avid cyclist and backpacker. Though he’s recently traded his carbon fiber racing bike for a kid-carrying cargo bike, he’s even more excited to go on adventures in nature these days, now with his wife and two young kids. Once they all go to sleep, he retreats to his workshop, where he finds new ways to make mistakes in building custom furniture in the Arts & Crafts and mid-century styles.

Noteworthy

Caleb once hacked his high school’s attendance database and, yes, deleted the records.