Head of Marketing

Location: San Francisco, CA Type: Full-Time Work Arrangement: In-office, San Francisco, CA

About Flai AI is creating category-defining companies across every industry. Automotive is next. Despite being one of the largest industries in the world, dealerships still rely on outdated systems and manual processes. Flai is changing that. We're building the AI platform redefining how dealerships operate. Backed by First Round Capital, Toyota Ventures, Y Combinator, SV Angel, and Liquid 2, we've hit product-market fit early and are growing fast.

The Opportunity This is a rare chance to build and scale Flai's marketing function at a company with insane momentum. You'll work directly with the founders to shape Flai's voice, tell customer stories, launch products, and help write the story that defines AI in automotive. The raw material is all here: measurable ROI, customers who love the product, and a market that's just beginning to pay attention to AI. This is the kind of role that's difficult to find twice. As Flai grows, marketing grows with it.

You'll Love This Role If…

• You'd rather build the playbook than follow one.

• You get energized by a blank page and move fast without needing layers of approval.

• You want your work to shape a company's trajectory, not just fill a content calendar.

• You're excited by AI and want to be early to something that actually matters.

What You'll Do

• Content: Own the content engine and set the strategic direction and brand voice across channels.

• Product marketing: Own messaging, competitive positioning, product launches, and customer use-case development — hands on, not just strategy from the sidelines.

• Brand strategy and positioning: Define what Flai stands for, how we differentiate, and how we communicate our story, and keep refining it continuously, not as a one-time project.

• Sales enablement: Own decks, one-pagers, case studies, battlecards, demos, and other sales collateral.

• Brand activation and merchandise: Define how Flai shows up at dealerships and in the market, from merch to on-site materials.

• Top of funnel and demand generation: Build and run the strategy that drives qualified pipeline. Own targeting, messaging, and channel performance, and use the data to prove what's working.

• Customer advocacy and growth loops: Build referral programs, customer advocacy, community, and other engagement or distribution loops.

• PR and company communications: Support announcements around fundraising, partnerships, product launches, and company milestones.

Who You Are

• 5+ years in product marketing, brand, or growth marketing at a B2B tech company, including real experience growing the top-of-funnel marketing function at an early-stage startup. Mid-market or SMB experience is ideal.

• Senior enough to think in big-picture strategy, but still hands on keyboard: you write the copy, build the campaign, and run the experiments yourself.

• Data obsessed: you can set up tracking and analytics, and use metrics to find the right audience and sharpen messaging, not just make directional gut calls.

• Curious about AI, energized by new markets, and comfortable figuring things out.

• High ownership, strong follow-through, and a bias toward shipping.

• Nice to have: AI or vertical SaaS background, founder brand building, and experience managing or mentoring a marketing teammate.

Why Flai Most marketers join after the story has already been written. This isn't one of those opportunities. You'll help write the story that defines this market from day one, backed by real customer proof, a product that solves a genuine problem, and the freedom to build something real.

What We Offer

• Competitive salary ($170K to $210K) and meaningful equity.

• Medical, dental, and vision.

• Flexible PTO.

• Hybrid SF office, 3 to 4 days a week with the founders.

• A small, high-caliber team where your work has real impact from day one.