Head of Content

First off I want to say – this is going to be a FUN role, with a LOT of creativity. It's a lot of work, but if you're a creative and want to build a very unique brand, this might be the perfect role for you. You'll be working directly with the CEO and Founder, an ex-YouTuber with 1 million followers and half a million YouTube subscribers, and the lead video editor who also boasts over 400 million organic video views on his own. We’re looking for a creative, strategic operator to help run and scale Dreamwell’s content engine—think more Washington Post than startup blog, mixed in with a YouTube talk show. This is not your standard B2B content role. You’ll be at the intersection of media, brand, and product—turning big ideas into sharp execution across video, social, newsletters, and more. This is a high-impact position with visibility and ownership. You’ll be joining as one of the first 12 full-time hires (and therefore have meaningful equity), working directly with the founder/CEO (a former influencer with over 1M followers) to bring our voice, narrative, and media presence to life. Note: We’re a remote-first company, but we meet in person every ~2 months (usually in Toronto) for a week of creative collaboration (and great food). You’ll need to be available for these sessions for this role. About Dreamwell Dreamwell is an AI-powered influencer marketing platform helping brands launch and scale campaigns with creators who actually drive results. We’ve raised $3M from top-tier investors including Tim Draper and Uber’s former performance marketing leadership. Our mission is to build the most effective influencer marketing platform for brands—and alongside it, a standout brand and content presence that earns attention and trust. The product should speak for itself, but how we show up in the world matters just as much. What You’ll Do • Own and operate our content system—strategy, editorial planning, production, and publishing across a media-style site • Shape and maintain Dreamwell’s voice across blog, video, and social • Work directly with our YouTube producer and video editor to ensure weekly longform content gets repurposed into platform-native clips (LinkedIn, Twitter/X, etc.) • Lead newsletter strategy and execution—writing, formatting, and ensuring consistency • Help manage social presence across company and founder accounts, especially LinkedIn • Leverage AI tools and automation (Zapier, Notion, Descript, Webflow, etc.) to scale content production • Coordinate with the CEO and other leads to align on brand, GTM moments, and product messaging • Maintain editorial standards across everything we ship—voice, tone, clarity, timing This Role Is For You If... • You think in narratives, not just assets • You’ve led content systems before—from idea to execution • You’ve worked with creative or production teams and know how to extract signal from chaos • You understand how video, social, and written content connect—and how to repurpose intelligently • You’re not afraid to get into the weeds: one day it’s shaping a story arc, the next it’s fixing a headline, the next it’s reviewing cuts for TikTok • You have a sharp editorial eye and care about tone, polish, and storytelling • You’re comfortable with a fast-moving founder who has vision but expects real autonomy in execution • You have real editorial instincts and know how to maintain narrative, quality, and flow across a publication—not just isolated content assets Experience Required • 6+ years in content strategy, editorial, or creative roles—especially in startups, SaaS, or media-led brands • Experience running multi-channel content (blog, email, social, video) • Strong writing skills with experience running newsletters or editorial calendars • Familiar with video-first content and what it takes to repurpose it for different platforms • Proficient with tools like Notion, Webflow, Descript, and light marketing ops • Comfortable using AI tools to streamline workflows and content production • Experience working with or alongside founders/execs to shape narrative • Highly organized, fast-moving, and not afraid to figure things out • Health savings account • Monthly wellness credit (fitness, gym, therapy, whatever works for you) • A lean, creative, no-BS team that actually moves fast • Occasional weekend and evening work, but maximum ownership and autonomy in return This is a pivotal hire. If you’re looking for a chill marketing job with guardrails and hand-holding and a regular 9–5 and don't message me after 5pm, this won’t be the right fit. But if you want to own something early, move fast, and help shape the voice of a brand from day one—this might be it. Looking forward to all you lovely creatives. Seniority level Seniority level Executive Employment type Employment type Full-time Job function Job function Marketing, Public Relations, and Writing/Editing Industries Software Development Referrals increase your chances of interviewing at Dreamwell AI by 2x Sign in to set job alerts for “Head of Content” roles. Senior Content Marketing Manager: Lead Gen and Creator Content We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI. #J-18808-Ljbffr