About Letterhead

Letterhead makes your newsletters work for you, aiding publishers and marketers in audience engagement, content creation, and revenue generation through automation and machine learning.

We're a venture-backed startup on a mission to redefine online engagement with meaningful, first-party content. Birthed from the media realm in 2022 by founders who built a nationwide network of local email newsletters, Letterhead now empowers every organization to master email.

Open Roles




Sales Development Representative
General Interest


Our Team

We're a diverse team of internally motivated, open-minded people who want to be the best at what we do. We value intellectual curiosity, candor, and a sense of urgency.

When we hire, we look for cultural contribution rather than cultural fit: what will each new person add to our team as we grow?

Our Values

Users first: we're here to help our customers and put their experience and priorities first.

Integrity: we're honest and transparent with each other and our stakeholders. We do what's right.

Servant leadership: our best work happens at the front line. Our leadership team exists to support and drive that forward.

Grit: Building something new is hard work. We stick with it, push through obstacles, and get the job done.

Perks and Privileges

Premium Healthcare

Retirement & Equity

Generous Time Off

Best-in-class health, vision, and dental insurance with full family premiums covered 100% by Letterhead.

401(k) plan with company match alongside stock options.

15 days of paid time off (PTO) per year, plus company holidays and additional tenure days each year.

Remote Flexibility

Professional Growth

Miami Meetups

A primarily remote work environment with a supportive and collaborative team.

Opportunities for professional growth and advancement within the company.

Occasional travel to our Miami office for team gatherings and strategy sessions.