Trolley AI is hiring: Social Content Creator & Strategist in San Juan

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Base pay range

$10.00/hr - $15.00/hr

• Location: Remote
• Type: Contractor (Part-Time, 20h/week, with potential to scale)
• Reports To: Project Manager & Production Lead
• Application Link: Submit Application

Who We’re Looking For

We’re hiring a Social Content Creator & Strategist with a strong editorial sense and experience creating short‑form video content for TikTok, Instagram Reels, YouTube Shorts, LinkedIn, X/Twitter, and Substack. The ideal candidate is deeply connected to U.S. social culture, news cycles, and creator‑driven content, knows what’s trending, and can translate a thought leader’s voice into engaging content across platforms.

Key Responsibilities

• Short‑Form Video Content Direction
  • Develop strategic short‑form video concepts for TikTok, Instagram Reels, YouTube Shorts, and LinkedIn.
  • Use raw or archival footage (Zoom, interviews, speeches, etc.) to map out video ideas and formats.
  • Provide clear editorial direction and references to guide editors, including hooks, pacing, captions, and tone.
  • Ensure edits feel native to the platform and reflect current visual and cultural trends.
• Social Media Trend Awareness & Content Repurposing
  • Stay up‑to‑date with platform trends, audio trends, editing styles, and viral formats.
  • Propose new video ideas, hooks, and transitions inspired by current social media culture.
  • Identify ways to repurpose long‑form content into short‑form clips, carousels, or quote graphics.
  • Adapt and remix existing content into fresh formats for TikTok, Reels, and carousels.
  • Write core copy and hooks; collaborate with Marketing Assistant on captions and variations.
  • Analyze competitor content and suggest improvements or new approaches.
  • Identify whitespace and opportunities to differentiate.
• Content Strategy & Editorial Cohesion
  • Lead the editorial tone across content formats in collaboration with the Producer and brand strategist, ensuring consistency in voice and message.
  • Translate brand pillars (Founder Mode, Diaspora Mindset, Progressive Capitalism) into weekly content themes and multi‑platform ideas.
  • Create structure around idea‑to‑content flow from Substack essays to POV clips, carousels, and social posts.
  • Ensure consistent voice, tone, and storytelling across all platforms.
• Platform Growth & Content Optimization
  • Review content performance and share insights on what works or needs iteration.
  • Collaborate with the team to refine tone, hooks, or angles to maximize impact.
  • Recommend ways to optimize video structure, captions, and publishing timing based on analytics or platform shifts.
  • Contribute ideas around how AI tools and automation could streamline the creative workflow and ideation process.
• Workflow & Delivery
  • Use ClickUp to manage all content ideas and track status.
  • Deliver clean, organized creative briefs, video references, and visual examples to editors.
  • Apply revisions and updates quickly and clearly.
  • Communicate proactively with the internal team to align on deliverables and timelines.
• Key Performance Indicators (KPIs)
  • Delivery of content aligned with brand voice and editorial strategy.
  • Execution of weekly content calendar with trend‑aware, high‑quality deliverables.
  • Strong contributions to brainstorms and strategic ideation.
  • Growth in platform engagement and content performance.
  • Cohesive storytelling and tone across formats and platforms.
  • Efficient communication and handoff process with editors and creative collaborators.
  • Ability to manage and deliver a healthy mix of evergreen, reactive, and archival‑based content weekly.

What You Bring

Required Skills & Experience

• 2+ years working on social‑first content strategies across platforms (TikTok, IG, LinkedIn, Twitter, YouTube).
• Working knowledge of short‑form editing and what makes a video perform.
• Strong storytelling instincts and understanding of editorial tone and timing.
• Ability to repurpose long‑form formats into digestible, high‑performing short‑form content.
• Up‑to‑date with platform trends, meme culture, and U.S. news cycles.
• Familiarity with creator economy voices and how to build a thought‑leadership brand.
• Confident in writing hooks, video references, content scripts, and caption direction.
• Clear communicator who works well with production teams and creatives.
• English fluency required.

Preferred Qualifications

• Experience working with digital creators, founders, or influencers.
• Experience developing content in collaboration with marketing teams.
• Familiarity with CapCut, Descript, mobile editing apps, Frame.io.
• Understanding of how to connect Substack, LinkedIn, and Instagram in a cohesive strategy.
• Spanish fluency is a plus.

Why This Role Is Important

You’ll help shape the social presence of mission‑driven founders and organizations, combining editing craft with cultural fluency to create impactful, trend‑aware content.

What to Expect: Our Application Process

• Apply through ClickUp.
• Complete a short assignment via TestGorilla.
• Interview with Recruitment & Ops Coordinator.
• Second interview or role assessment.
• Final interview with Founder & CEO.
• Welcome to Trolley!

About Us

Trolley is a fast‑growing creative operations company delivering high‑impact digital and marketing solutions. We collaborate with high‑profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated powerhouse, combining strategy, design, production, and performance analysis to deliver world‑class results.

AI Mindset & Continuous Innovation

Our team works with an AI‑first mindset, and we look for people who are genuinely excited about using technology to make their work faster, smarter, and more creative. Everyone at Trolley integrates AI into their daily work, and we expect new team members to contribute to this culture of curiosity, experimentation, and continuous improvement. New tools and capabilities are constantly emerging, and as a team, we’re learning in real time, testing, exploring, and figuring out what actually moves our work forward. We value curiosity, experimentation, and a willingness to try new approaches.

We value people who:

• Use AI to support research, organization, content development, and problem‑solving.
• Stay open to learning new tools and proactively share discoveries with the team.
• Look for ways to simplify workflows and increase efficiency without sacrificing quality.
• Use AI thoughtfully, keeping brand voice, strategy, and context at the center.
• Collaborate with the team to strengthen our internal systems and creative output through informed AI usage.

Our long‑term vision is clear: we believe AI will become the standard operating model for creative and production teams across the industry. We’re doing the work early so that, as this shift becomes the norm, Trolley is already operating as an expert and industry leader. We want people who are excited to grow with this evolution and help us stay ahead of what’s coming.

We Operate Under Founder Mode

Trolley is built on a Founder Mode mindset – an operating system rooted in ownership, strategic thinking, and execution at speed. Here, we look for people who take initiative, think like entrepreneurs, and use tools like AI to optimize how work gets done. Founder Mode isn’t about going it alone – it’s about working within high‑trust, collaborative teams where contribution matters more than control. We value creativity, resourcefulness, and clear communication. If you’re driven by impact, thrive in dynamic environments, and believe in scaling through systems, not stress – this is the place for you.

Why Join Us?

• Work with the Best: We recruit globally to connect top talent with forward‑thinking companies.
• Tech‑Driven Efficiency: Leverage the latest AI and tools to amplify your impact.
• Human‑Centric Approach: Our systems are designed to support and elevate people, not replace them.
• Training for Success: We provide world‑class training to ensure you excel in every aspect of your role.

Benefits at Trolley

• Work from anywhere.
• Flexible schedule and time off with no micromanaging.
• Direct collaboration with the Founder.
• Access to top‑tier AI tools (Perplexity, ChatGPT, ClickUp Brain and more).
• Clear path for long‑term career growth.
• A supportive company culture grounded in ownership and prioritizing progress over perfection.

Seniority Level

Not Applicable.

Employment Type

Full‑time.

Job Function

Marketing, Public Relations, and Writing/Editing.

Industries

Technology, Information and Media.

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