Head of Marketing

Location: San Francisco, CA
Type: Full-Time
Work Arrangement: In-person 5 days a week at our SF office

AI has transformed B2B SaaS, but has struggled to penetrate the real-world industries that shape our lives. Flai is building the leading AI-native communications platform for car dealerships.

A $1.3 trillion industry, auto dealerships sell 96% of the 16 million new cars sold each year. Yet they universally run on outdated systems and manual processes, which is why dealerships spend $36B each year on operations. That’s our opportunity.

We launched our first voice AI product a year ago. Since then, we have deployed multiple products across hundreds of dealerships across the U.S. We’ve partnered with the 2nd largest automaker in the country and many of the leading dealership groups. We’ve raised funding from leading VCs including First Round Capital, Toyota Ventures, Y Combinator, Innovation Endeavors, SV Angel, and Liquid 2.

We’ve grown insanely quickly with a small, scrappy team and continue to move at that pace.

The Opportunity

You'll work directly with the founders to shape Flai's brand, tell customer stories, launch products, and help write the playbook to build a differentiated identity. The raw material is there: measurable ROI, customers who love the product, and a market that's woken up to AI’s immense potential. You’ll start hands-on and eventually earn a team by proving the motion.

Our typical buyer is the store’s general manager. They are not primarily on LinkedIn/X, don’t read tech press, and constantly get pitched by vendors. The winner in the category will be the company that dealers have heard of, trust, and can point to a peer already using the product.

We want a marketer who is interested in solving this different kind of challenge.

Who You Are:

• You want to be close to the physical world: dealerships are high-stakes environments where trust is earned slowly and can be lost even faster.

• You’d rather build the playbook than follow one: you generate ideas, test relentlessly, and quantify what works.

• You are a player-coach: senior enough to think big picture, but willing to do it yourself. Over time you’ll grow your scope via additional team members, contractors, agencies, and automation.

• You are high ownership: strong follow-through, and a bias toward shipping.

• You are data-obsessed: you are rigorous about generating hypotheses and quantifying results.

• You're AI-native: you want to push the boundaries of what is possible in marketing, but also understand the importance of human taste and judgement.

• You’re ambitious: you want your work to shape a company’s trajectory, not just fill a content calendar.
  

What You'll Do:

Make the best product in the category obvious. We win head-to-head evaluations, and customers who try us keep us. But being better isn't good enough. We want to be the leading brand. You'll decide how Flai is positioned, our value props and differentiators, what language makes our buyers tick, and how to distribute that consistently across channels.
Build a story that grows with us. We started with voice; now the product surface is expanding fast. You'll set positioning that still holds when Flai does considerably more than today, and own how we reveal that over time.
Turn our results into the industry's reference numbers. Our customers see incredible ROI, but we are still early when it comes to translating that for other customers: case studies, benchmark data, proof a buyer can verify in ninety seconds, etc. In a market where every vendor claims results, we want irrefutable evidence of how we’ve transformed our customers’ operations.
Drive top of funnel by reaching buyers who aren't online-first. Our customers are dealership owners and operators. Flai’s success is built on referrals and field events. We’re looking for a marketer who can help us scale these channels first, then test other growth vectors. There's no SaaS playbook for this. You'll have to write it.
Equip our AEs with the right assets. Our sales team needs consistent narrative, competitive positioning, and proof points at their fingertips to win every conversation. You’ll be in charge of figuring out what that is and iterating quickly to refine the messaging.
Then scale our voice. As the loops prove out, we expect a lot of the work can be scaled via automation and, when necessary, additional headcount.

Requirements

• 4+ years in product marketing, brand, or growth marketing at a high-growth tech company; experience owning the top-of-funnel marketing function at an early-stage startup.

• This is a build-from-zero seat, not a big-company marketing seat. You need to be comfortable figuring out what problems matter, how to solve them, and showing the results.

• To move as quickly as we do, we work in person in San Francisco 5 days a week.

Nice-to-have:

• Experience selling into real-world industries, mid-market segments, or low-trust segments

• Experience managing or mentoring a marketing teammate.

• Experience across other GTM functions is a plus

What We Offer

• Competitive salary ($180K to $230K) and meaningful equity.

• Medical, dental, and vision.

• Flexible PTO.

• SF office.

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