Head of Marketing

Plain is redefining customer support for the next generation of B2B companies. We're building the fastest, most powerful platform to help companies move beyond reactive support and build true customer relationships.

Some of the world's most forward-thinking companies, like Cursor, Ashby, and Sanity, trust Plain to unify all customer interactions, enable faster team collaboration, and supercharge their workflows with AI.

We're a small, tight-knit crew with offices in SF and London. This role is hybrid with 3 days a week in our SF office.

Why this role is special

B2B customer support is undergoing a seismic shift. AI is transforming the way companies engage with customers, shifting support from a siloed function to a company-wide effort across Slack, Discord, and in-product experiences. Plain is at the center of that shift, and we're hiring our first Head of Marketing to own the story.

We’ve been able to build the brand to date with minimal marketing resources, and we’re really excited about what we can do with an owner of the function. You'll build the narrative, own the full marketing function, and have real resources to grow a team. You'll inherit two strong players on day one (a Head of Demand Generation and a Head of Community) and report directly to Simon, our CEO.

What you'll do

• Own the narrative. Build the positioning and story that makes Plain the default choice for modern support teams. Partner closely with Simon to shape and evolve it, but bring your own taste and conviction to every launch, campaign, and touchpoint.

• Make the message stick. Own consistency across every channel so the Plain story lands the same way whether someone finds us on Twitter, at an event, or in a sales conversation.

• Build the function. Grow the team from two to five-plus in year one. Stand up the operating model: narrative frameworks, launch infrastructure, tight feedback loops with Sales and Product.

• Drive GTM. Run a cohesive, experiment-driven go-to-market motion. You should know enough about demand gen to prioritize and unblock, but this isn't a hands-on DG role.

• Move the numbers. You'll know it's working when share of voice is growing, brand awareness is climbing, and inbound pipeline is getting stronger.

• Stay close to the business. Build tight feedback loops with Sales and Product so the narrative stays sharp and launches land with impact.

This is a great fit if you…

• Have led a marketing org at a B2B SaaS company and have a strong point of view on brand and narrative. Exposure to developer tools or technical buyers is a plus.

• Bring a product marketing mindset: you’re curious about the customer, the market, and the “why” before you think about the “what.”

• Have proven experience owning a narrative from blank page to market.

• Have sharp instincts for what great marketing looks like, and the conviction to push for it even when it's uncomfortable.

• Care about pipeline and data-driven results just as much as you care about craft.

• Are energized by ambiguity. You don't need a playbook to get started.

• Can turn complex, technical ideas into clear and compelling stories.

• Want to build something meaningful alongside a founder, not just execute a plan.

This won't be the right role if you…

• Do your best work with an established brand, a big budget, and a large team behind you. We're early, and the fun part is building from scratch.

• Need a lot of process and structure before making decisions. We have strong traction, but we're still figuring things out.

• Prefer long approval chains and agency support. We're lean and we move fast.