Director, Marketing

About Letterhead

With Letterhead, your newsletters do all the work for you. We help publishers and marketers engage their audience, create great content products, and generate revenue, with software that can automate and support the entire process through machine learning.

We're a venture-backed scale-up on a journey to change how online engagement happens through meaningful, first-party content. Our founders came from the media industry, building a national network of local email newsletters, and spun out Letterhead in 2022 to help every organization master email.

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 culture fit: what will each new person add to our team as we grow?

This position is remote and this person can sit anywhere in the US. We are a global team and prioritize great people over location.

Our Company Values

• Users first: we're here to help our customers, and we put their experience and priorities first.
• Great and fast: we deliver top-quality work and experiences at high speed, every time.
• Extreme ownership: we take pride in owning our work and owning the mission, even when something’s “not my job,” we work together to make it happen.

About the role

Letterhead has product-market fit with sophisticated publishers. We're moving upmarket and entering a pivotal next chapter in which this person will play a key role. As we position ourselves as the only newsletter operating system for organizations running multiple newsletters, we need someone who can define our narrative, build our go-to-market motion, and establish the marketing foundation from scratch.

We're hiring a Marketing Director who will sit at the intersection of positioning, demand generation, and GTM strategy. You'll help define how Letterhead shows up in the market, including but limited to: translating complex product value into clear messaging, designing the motions that drive qualified pipeline, and building the processes that allow marketing to scale.

This isn’t just another optimization role. This is true, once-in-a-lifetime definition work.

In this role, you will:

• Own Letterhead's positioning and narrative, defining who we're for, sharpening our story as an operating system (not just another ESP), and partnering with leadership on decisions that shape product and roadmap.
• Design and execute go-to-market strategies for our ICP, deciding quickly which channels and programs are worth investing in.
• Build enablement materials that actually convert, working directly with the team to improve pipeline quality, deal velocity, and close rates.
• Launch and iterate on demand generation experiments across content, partnerships, events, and outbound.
• Establish the marketing foundation for what comes next: defining what "good marketing" looks like at Letterhead, building lightweight processes and standards, and deciding when to hire, outsource, or stay lean.
• Create compelling, persona-focused content including messaging frameworks, pitch decks, case studies, and sales collateral.
• Build lightweight reporting that ties marketing effort to pipeline outcomes, killing weak signals fast and doubling down on what works.
• Serve as a strategic partner to the CRO, with direct influence on company-level decisions around narrative, product positioning, and growth strategy.

You might thrive in this role if you:

• Have built or rebuilt a go-to-market function at an early-stage or transitional company, taking it from undefined to operational.
• Have, or can develop, strong opinions on positioning and messaging, and know how to defend them with clarity and evidence.
• Have experience marketing complex products to sophisticated, skeptical buyers who don't respond to generic pitches.
• Feel comfortable working directly with founders and cross-functional leaders, influencing company-level strategy with data and conviction vs waiting to take orders. 
• Have a bias toward focus, saying "no" as often as "yes" because you understand that constraints create clarity.
• Bring both strategic thinking and executional strength when it counts, and are as energized by setting strategy as you are doing the building. 
• Are data-informed but not data-paralyzed, using metrics and qualitative signals to refine your approach and kill what's not working.
• Experience in B2B SaaS, enterprise sales, media/publishing, and/or marketing tools is a bonus, but we care more about how you think than where you've been.

What we offer you:

• Remote-first and always workplace.
• 4 weeks paid time off.
• Best-in-class benefits package; most plans fully employer-sponsored for you and your family.
• 401k plan
• Stock option package commensurate with experience.
• The chance to make an impact at a fast-growing and successful scaleup company.

Letterhead is an equal opportunity employer and values diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other protected status. Any gender-specific terms should be understood to be applicable to all genders and not sex or gender limited.