Chief of Staff

Job Title: Chief of Staff at SkyDiamond Media – “Pivot” Required!

SkyDiamond Media is seeking a seasoned Chief of Staff to join our fast-paced, dynamic team. This role is for someone who thrives in the grey areas, can pivot quickly between tasks, and is comfortable working in completely unrelated aspects of the business. One moment, you could be coordinating with the kids’ tutor, and the next, you’re helping to scope a $500k contract. No task is too small or too big – you’ll be the right hand to a serial entrepreneur with multiple businesses, aging parents, and kids.

What we’re looking for:

• PA/EA experience: A background supporting high-level executives with a blend of personal and professional duties.
• Versatility: Must be comfortable navigating between wildly different tasks with speed and precision.
• Attention to Detail: Your focus on the details will help keep the CEO’s world running smoothly and efficiently.
• Trustworthy: This is a role built on trust. You’ll be trusted with sensitive family matters, major business decisions, and everything in between. NDA required!
• Work Ethic: This job is not for the faint of heart. We’re looking for someone who thrives in a fast-paced environment and isn’t afraid to jump into any task.
• Travel Planning: Experience in organizing complex travel logistics for both business and personal travel.
• Paralegal or Agency experience (a plus): Any legal or agency experience will be an added advantage in this multi-faceted role.
• HR Management (a plus): HR experience will be an asset, particularly in team building and supporting employee needs.
• Operational Leadership: Experience in overseeing operations to ensure efficiency, growth, and day-to-day success.
• Strategic Communication: Strong communication skills, both internal and external, are key to ensuring alignment across the board.
• Event Planning: Experience in planning both business events and personal gatherings is essential.
• EQ Savvy: Strong emotional intelligence to navigate complex relationships with ease and empathy.

What you’ll be doing:

• Managing both personal and professional calendars, coordinating meetings, and ensuring the CEO stays ahead of his day-to-day.
• Managing contracts, correspondence, and other operational tasks.
• Handling confidential matters with the utmost discretion and professionalism.
• Communicating across business entities, family needs, and personal life.
• Coordinating travel logistics and accommodations for business and personal trips.
• Assisting with HR matters and supporting team dynamics.
• Organizing strategic meetings, events, and initiatives.
• Driving operational efficiency across teams and functions.

Additional Requirements:

• Must pass a drug screening and background check.
• Salary range: $75k-$100k DOE.

If you're someone who loves the challenge of balancing multiple priorities, working in a high-trust environment, and most importantly—pivoting with ease—SkyDiamond Media wants to hear from you! Apply today if you’re ready for a role that requires both exceptional versatility and attention to detail. To test your attention to detail, attach a cover letter that answers the following question: If you could be any superhero (good or bad), who would you most identify with?

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