Rebekah Monson

WORK HISTORY

EDUCATION

SKILLS

ABOUT REBEKAH MONSON

Are journalism and tech operations completely different?I used to think so — until I realized that both require the same skills: listening deeply, asking great questions, understanding people, and creating clarity in chaos.Hi, I’m Rebekah — serial startup founder and COO of Letterhead, a platform that helps publishers automate workflows, centralize control, and drive revenue from their newsletter businesses. I lead across product, operations, and strategy, helping teams use data, automation, and creativity to grow audience and impact.Before Letterhead, I co-founded WhereBy.Us, a newsletter-first local media startup, and helped lead it from concept to a multi-city network. Earlier, I worked in communications at the University of Miami and began my career in local journalism, reporting and designing information that served my community.That foundation in storytelling and design still shapes how I build: start with curiosity, solve real problems, build for clarity, scale with systems.As a founder and operator, I’m drawn to complex problems — the kind that live at the intersection of media, tech, and human behavior. I’ve led cross-functional teams, raised capital, established lasting relationships, and built our company and its infrastructure from zero to millions in ARR.That same commitment to community drives how I lead. I serve on the boards of LION Publishers, Nu Deco Ensemble, and The Miami Foundation — supporting innovation, equity, and local impact.If you’re building something at the crossroads of product, media, or mission-driven business — or just trying to make the work *work better* — I’d love to connect.The best way to reach me is through my site: https://rebekahmonson.com