Remote Executive Program Specialist

for Flywheel Holdings

At Flywheel Holdings, speed and structure are our superpowers. As the Executive Program Specialist, you’ll act as the President’s right hand and systems integrator—protecting executional flow, enforcing accountability, and ensuring that no project, task, or red light slips through the cracks.

You are the operational enforcer for Flywheel’s core ventures: Ready Roles, USAHL, and Big League Movers. From team-wide follow-up to recruiting oversight, you own the systems, timelines, and playbooks that drive execution forward. This role is ideal for a strategic operator who loves holding the line, following up relentlessly, and keeping the CEO out of the weeds.

• Audit shared Todoist boards three times per week across Flywheel ventures.
• Flag overdue, missing, or unclear tasks and follow up with task owners directly.
• Reassign or escalate issues where tasks are blocked or forgotten.
• Track Steven’s own open loops and reset priority or clarity as needed.
   

• Monitor breakdowns across Ready Roles, USAHL, and BLM.
• For every red light, clarify:
   
  • Who owns it?
  • What’s blocking it?
  • Has it been acknowledged?
     
• Escalate unresolved issues after 48 hours with a one-line summary and solution.
   

• Build and maintain timelines for launches, onboarding rollouts, and initiatives.
• Track SOP rollouts, adoption, and milestone completion.
• Reboot stalled projects with clear next steps and updated assignments.
   

• Maintain a Flywheel-wide system rollout tracker across brands.
• Schedule implementation checkpoints and refresher tasks.
• Ensure team members complete assigned system steps.
• Coordinate Loom videos or visual aids with EA – Ops & Content as needed.
   

• Review recruiting dashboards weekly:
   
  • Active assistant/app setter/data activator pools
  • Time-to-fill and client delivery turnaround
  • Aged leads or candidate bottlenecks
     
• Escalate funnel breakdowns to EAOM with context and proposed action.
   

• Monitor CRM or lead sheets for stagnation or dropped follow-up.
• Escalate any leads uncontacted for over 48 hours.
• Flag inconsistencies or bottlenecks in the Sales Strategist’s pipeline cadence.
   

• Send a concise Monday execution brief to the President covering:
   
  • Unresolved red items from the previous week
  • Current risks (tasks, ops, recruiting, sales)
  • Systems adoption status
  • Recruiting pool health
  • Any required decisions or directional input
     

Follow-Through Obsessed – You believe in clear ownership, on-time delivery, and follow-up until done.

Strategic Operator – You understand the business context behind the project and can translate goals into executable workflows.

Calm Under Pressure – You manage multiple deadlines, people, and priorities without overwhelm.

Proactive Communicator – You speak up early, escalate clearly, and make it easy for others to follow through.

• 3+ years in operations, project management, or executive support roles.
• Experience managing task boards, timelines, and cross-functional systems.
• Strong documentation, reporting, and follow-up skills.
• Comfortable managing up, across, and down.
• Familiarity with staffing, recruiting, or remote-first teams is a plus.

• You avoid chasing others or redirecting unclear work
• You wait to be told what’s off instead of finding it
• You prefer operating inside a single department or function
• You dislike enforcing deadlines or dealing with cross-functional teams
   

• You treat operational gaps like puzzles to solve
• You are energized by making things run smoother and faster
• You’re confident following up with executives and holding the line
• You enjoy spotting issues before they snowball and surfacing clean solutions
• You’re the one everyone counts on to finish what others started
   

If you’re ready to turn chaos into clarity, hold teams accountable, and drive real operational execution across Flywheel’s ventures, we want to hear from you. Apply today to become the engine behind our systems and the driver of our strategic momentum.