Head of Content & Creative

Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill for a world being rewritten by AI. We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M from world-class investors. Ambition is sacred to us, and we've built a product that takes that seriously.

About the Role

We're hiring our first Head of Content & Creative to build the content engine at Leland. We're sitting on a huge amount of great material, including expert coaches, livestreams, courses, and customer stories, and far too little of it reaches the people who'd benefit from it. You'll set the strategy and calendar across blog, editorial, webinars, social, and research, and you'll own how Leland looks and sounds everywhere, from campaign concepts down to the visuals in an ad. You'll start hands-on and build a team, beginning with a Social Media Manager who reports to you. Over time this role grows could grow into leading all of content at Leland as we turn it into a real media brand. If you're a sharp writer and storyteller with a designer's eye and want to build something from scratch, we'd love to chat with you!

What You'll Do

Build the content engine

• Set content strategy and own the editorial calendar across blog, newsletters, webinars and livestreams, whitepapers, and social
• Put the processes, tools, and AI workflows in place so we publish consistently without relying on heroics
• Build with search in mind, both traditional SEO and AI search, so Leland shows up and gets cited when people look for answers we're qualified to give
• Measure what's working (traffic, engagement, and influence on pipeline and bookings) and double down on it
• Work closely with the rest of the marketing and design team on web visuals, positioning, messaging and overall website structure

Put Leland's point of view into the world

• Champion original research and reports on admissions, careers, and AI at work, drawing on our data, coaches' expertise and other Leland points of view
• Turn coaches, customers, and our own team into content through interviews, case studies, and LinkedIn employee advocacy
• Build relationships with journalists, podcasts, and newsletters, and pitch stories that get Leland into the conversation

Lead brand and creative

• Lead the Leland brand (in partnership with Design) across every channel and keep it sharp and consistent as we grow
• Concept and lead integrated campaigns, multi-week efforts that tell one story across paid, lifecycle, social, events, and sales
• Be the creative partner to performance marketing, lifecycle, AI Programs, and sales on ad creative, landing pages, decks, and emails
• Get hands-on with design and video when it makes sense, and direct freelancers or AI tools when that's the better call

Build the team

• Manage our Social Media Manager, AI & Automation, and help shape how the content team grows from here

About You

• 5+ years in content, brand, or creative, including time building a content program at a startup or high-growth company (consumer, B2B SaaS, or ideally both)
• An excellent writer and editor with strong opinions about what good looks like
• Real design sense and hands-on skills in tools like Figma, Canva, Claude Design and more; you can make a strong visual yourself, not just brief one
• A portfolio that shows both editorial and creative work
• Solid SEO fundamentals and a sense of how search is changing with AI discoverability
• AI-native: you use tools like Claude or Midjourney every day and have built workflows that save you real time
• Organized and systems-minded; you like building the machine as much as making the work
• Experience managing or mentoring at least one person
• Bonus: video production and editing skills, PR or media relations experience, or a background in media or publishing

Why Leland?

• The chance to join a world-class team helping people achieve their career and educational dreams
• Work in a collaborative, high-energy environment where your contributions have a direct impact
• Operate in a fast-paced, AI-native environment
• We don't hire people who merely want to work for a great company; we hire people who want to make a great company

Leland is an equal opportunity employer. We encourage candidates of all backgrounds and demographics to apply.