Creative Content Creator Jobs in Chicago, IL (NOW HIRING)

Department: Office of the CEO

Reports To: Chief Executive Officer

Location: Berwyn, IL — Extensive Travel Required

Status: Full-Time, Exempt

Travel Requirement: Up to 80% — Domestic and International, Including On Short Notice

About Realty of America

Realty of America, LLC (ROA) is a fast-growing national real estate brokerage headquartered in Chicago, Illinois, with operations spanning multiple U.S. states and an office in Colombia, South America. ROA is committed to empowering agents and Designated Brokers with the tools, support, and leadership needed to thrive in every market we serve. We are an equal opportunity employer.

Position Summary

Realty of America is looking for a sharp, fast-moving Personal Videographer & Social Media Content Creator to work exclusively alongside our CEO. This is not a studio role — it is a lifestyle role. You will be by the CEO’s side at events, on the road, and in the field, capturing real moments in real time and turning them into quality short-form content that is live on social media the same day. Speed, instinct, and consistency matter more here than cinematic perfection. The ideal candidate is mobile-first, social-savvy, and ready to travel at a moment’s notice. If you thrive in fast-paced environments, are always reaching for your phone to capture a moment, and understand how to build a following through authentic content — this role is for you.

What This Role Is Really About

This is a high-energy, always-on content role built around one goal: growing the CEO’s social presence and ROA’s brand through consistent, engaging, real-time video content. You will not be waiting for a production schedule. You will be capturing content as life happens — at speaking engagements, agent events, market visits, meetings, and on the road — and getting it posted quickly. The emphasis is on quality that is achievable on a phone, fast turnaround, and content that connects with an audience.

Travel Expectations

Travel is a core and non-negotiable part of this role. Candidates must be genuinely comfortable with a schedule built around the CEO’s calendar, which changes frequently and often with little advance notice.

• Travel directly with the CEO to speaking engagements, company events, state market visits, agent meetings, and industry conferences.
• Be available to travel on short notice — sometimes within 24 to 48 hours of a trip being confirmed.
• Domestic travel across all ROA state markets on a regular basis.
• International travel as needed, including to ROA’s operations in Colombia, South America.
• Estimated travel commitment of up to 80% of working time.

Key Responsibilities

Real-Time Content Capture

• Be present at all CEO engagements — events, meetings, travel, and appearances — and capture content as it happens.
• Record short-form video content using a smartphone, prioritizing speed, authenticity, and platform-readiness.
• Capture key moments, quotes, energy, and behind-the-scenes content that tells the story of the CEO and the ROA brand.
• Anticipate content opportunities before they happen — always be ready, always be recording.
• Operate with discretion and professionalism in executive-level and client-facing environments.

Fast-Turn Editing & Social Publishing

• Edit and publish content the same day it is captured — quick turnaround is essential.
• Work primarily from a smartphone using mobile editing tools (CapCut, InShot, or similar) to edit and upload directly.
• Add captions, text overlays, music, and platform-appropriate formatting before publishing.
• Post content across Instagram, TikTok, LinkedIn, and other platforms as directed, optimized for each channel.
• Maintain a consistent posting cadence to build and sustain social audience growth.

Social Growth & Audience Building

• Take active ownership of growing the CEO’s social media following across platforms.
• Develop a consistent content style and voice that reflects the CEO’s brand and personality.
• Use trending formats, sounds, and platform features to maximize reach and engagement.
• Monitor content performance and adjust approach based on what resonates with the audience.
• Bring creative ideas for series, recurring formats, and campaigns that build a loyal following over time.

CEO Partnership & Content Planning

• Work closely with the CEO to understand his vision, messaging goals, and what he wants his brand to communicate.
• Align on a weekly content plan while staying flexible for real-time and unplanned opportunities.
• Serve as the CEO’s primary content partner — proactive, responsive, and always thinking about the next piece of content.
• Coordinate with ROA’s marketing team to ensure content aligns with broader brand initiatives.

Qualifications

• 2+ years of experience in videography, social media content creation, or a related field.
• Strong portfolio of short-form video content with demonstrated results across social platforms.
• Mobile-first shooting and editing mindset — highly proficient with smartphone video and mobile editing apps.
• Deep familiarity with Instagram Reels, TikTok, LinkedIn video, and YouTube Shorts.
• Ability and genuine willingness to travel extensively, including internationally, sometimes on very short notice.
• Fast editor who can turn content around same-day without sacrificing quality.
• Strong understanding of social media trends, platform algorithms, and what drives engagement.
• Professional, personable, and comfortable in executive and high-profile settings.
• Self-starter who takes initiative and does not need to be told when to hit record.

Preferred Qualifications

• Experience working as a personal videographer or content creator for an executive, public figure, or personal brand.
• Proficiency with Adobe Premiere Pro, Final Cut Pro, or DaVinci Resolve for higher-production edits when needed.
• Experience growing a social media account from the ground up.
• Familiarity with real estate, brokerage, or business content.
• Spanish language proficiency is a plus given ROA’s operations in Colombia/Puerto Rico