Founding Content Lead

Location:San Francisco (In-Office)Reports to:CEOCompensation:Competitive cash + meaningful equityThe ProblemCommercial insurance is a $100B+ market with zero consumer brand. Geico has a gecko. Progressive has Flo. Small business insurance has... nothing. It's a sea of sameness—commoditized, forgettable, invisible.36 million businesses in America need insurance. Most of them feel ignored, confused, or ripped off by an industry that hasn't evolved in decades. Nobody speaks for them.Harper is building an AI-native brokerage that actually works. But we're not trying to be another basic insurance company. We want to become the voice of small business in America—and show the world what happens when AI and humans work together seamlessly.We have real operational receipts, a sharp point of view, and stories worth telling. What we don't have is someone to bring that to life across every format, everywhere.The ThesisThe companies that win the next decade will own their narrative. Founder-led content is the highest-leverage motion—it compounds, it's defensible, and it filters for the exact candidates and customers who belong here.But this isn't just about the founder talking to a camera. We're going to be in the field with business owners. We're going to show what AI-powered service actually looks like from the inside. We're going to build something people watch, share, and remember.Short-form. Long-form. YouTube. Whatever the format, wherever the platform—we need someone who can develop the entire strategy and own execution end-to-end.The RoleYou'll build Harper's content engine from zero. Strategy, production, distribution—all of it. You're not managing a process; you're creating a media arm for a company that wants to define a category.Own the entire content strategyDevelop Harper's content vision across all formats: short-form (TikTok/Reels/Shorts), long-form (YouTube), LinkedIn, X, and whatever's nextBuild the editorial calendar, content pillars, and distribution playbookMake Harper the voice of small business owners—not just an insurance company with a social presenceProduce content everywhereRun founder-led production: direct shoots, manage recording blocks, turn raw footage into polished contentGet in the field—shoot with real business owners, capture their stories, show the human side of what we doCreate content that shows how AI and humans blend seamlessly at HarperExecute at every levelRecord, edit on the fly, post, iterate—you can do the whole thing yourselfKnow the creator ecosystem: tools, trends, formats, what's working right nowSet up contractors/editors as needed, but never lose the ability to ship soloBuild toward scaleAs this grows, you'll build a teamCreate the systems, playbooks, and standards that let Harper's content operation scale without losing quality or voiceMeasure What MattersTie content to outcomes: recruiting inbound, investor/operator engagement, brand perception, and eventually demandWeekly review rhythm: what worked, why, what we double down onWhat Success Looks Like30 Days:Shipping daily across platformsContent strategy documented: pillars, formats, cadence, distribution planFirst field content captured with real business ownersRecording + publishing rhythm locked in90 Days:Harper is consistently shipping 5-10 shorts/week + regular long-form contentClear format winners emerging—repeatable, high-performing templatesRecruiting pipeline noticeably improves ("I found you through your content")Brand perception shifting: Harper is the one people pay attention toYouTube strategy in motion12 Months:Harper is recognized as the voice of small business insuranceContent is a meaningful driver of recruiting, credibility, and demandYou're leading a team and the function runs without founder dependencyWho You AreYou're a builder, not a manager. A producer who can also be the talent. Someone who thinks in systems but ships like a creator.You've built content that actually performed—not just posted, but moved numbersYou can develop strategy AND execute it yourselfYou know how to direct talent and pull great performances out of busy peopleYou can pick up a camera, record, edit, and post—today, not after you hire someoneYou understand the creator ecosystem: platforms, tools, trends, algorithmsStrong storytelling instincts; you write hooks that stop scrollYou work fast without making things feel cheapYou thrive in ambiguity and take full ownershipBonus:Built content functions for startups, creators, or high-growth companiesExperience with employer brand or B2B content that doesn't feel like B2BUnderstand regulated categories (finance/insurance) and can stay compliant without becoming boringHave produced long-form (YouTube, documentary-style, podcasts)Requirements3+ years in content production / creative ops (or equivalent body of work that speaks for itself)Portfolio that shows range: short-form, long-form, ability to build an audience or drive outcomesBased in San Francisco or relocatingWorking at HarperHarper runs like a high-performance desk:High standards, low egoFast feedback loopsDirect communicationExtreme ownershipSystems > heroics (but we love people who can do both)How to applySend the following to Your portfolioA video telling me why you're the person to bring this to lifeCompensation Range: $80K - $110K