Executive Operations Assistant to CEO

📍 Raleigh, NC (In-Office Preferred)

💰 Salary: $65,000 – $85,000 + Performance Bonus Opportunities

Red Crow Holdings is a growing holding company with businesses in healthcare, transportation, insurance, and professional services.

We are seeking a highly organized, proactive, and execution-focused Executive Operations Assistant to work directly alongside the CEO to help build systems, improve accountability, coordinate strategic initiatives, and support operational growth across multiple companies.

This is not a traditional administrative assistant role.

This position is ideal for someone who enjoys solving problems, managing projects, building processes, tracking performance, and helping organizations scale.

You will serve as a key extension of the CEO and play an important role in creating the operational infrastructure needed to support long-term growth.

• Pinnacle Freight Solutions
• Red Crow Management
• Heavenly Sent Home Care Services
• Affluent Logistics & Transportation
• Alpha & Omega Insurance Group

• Manage and coordinate strategic initiatives across multiple companies
• Track project deadlines, deliverables, and implementation timelines
• Follow up with managers to ensure accountability and execution
• Coordinate cross-company projects and priorities
• Prepare executive meeting agendas, notes, and action plans
• Maintain executive project trackers and implementation dashboards

• Collect weekly KPIs from company managers
• Maintain executive dashboards and scorecards
• Track performance metrics across all businesses
• Identify missing data, reporting gaps, and operational bottlenecks
• Prepare weekly executive summary reports
• Support decision-making through accurate reporting and analysis

• Coordinate implementation of recommendations from consultants, advisors, accountants, and legal partners
• Maintain project plans and implementation timelines
• Track action items and ensure follow-through
• Gather supporting documentation for financial and operational initiatives
• Provide progress updates directly to the CEO

• Track company certifications, licenses, renewals, and compliance requirements
• Maintain compliance calendars
• Coordinate documentation submissions
• Support audits, credentialing, and regulatory requests
• Ensure critical deadlines are not missed

• Manage CEO calendar and scheduling
• Coordinate meetings and appointments
• Organize executive communications
• Track follow-up items and commitments
• Assist with travel arrangements and meeting logistics
• Maintain organized company files and documentation

• Assist with SOP development and documentation
• Help implement process improvements and automation initiatives
• Support CRM, ClickUp, Google Workspace, and operational systems
• Maintain organizational structure and documentation standards

You may be a strong fit if you are:

✅ Extremely organized

✅ Detail-oriented

✅ Naturally proactive

✅ Strong at follow-through

✅ Comfortable holding others accountable

✅ Technology savvy

✅ Able to manage multiple priorities simultaneously

✅ Professional, confidential, and trustworthy

✅ Excited about helping build and scale businesses

• 3+ years supporting executives, founders, or business owners
• Experience in project management, operations coordination, or executive administration
• Strong Google Workspace and Microsoft Office skills
• Experience with ClickUp, Asana, Monday.com, Airtable, or similar platforms
• Experience building dashboards and KPI reporting systems
• Experience coordinating multiple projects simultaneously
• Healthcare, transportation, insurance, accounting, compliance, or multi-company experience preferred

• PMP (Project Management Professional)
• CAPM (Certified Associate in Project Management)
• Lean Six Sigma
• Scrum Master Certification
• Google Project Management Certification

The successful candidate will:

• Implement a company-wide KPI reporting process
• Establish executive dashboards and scorecards
• Organize compliance and certification tracking systems
• Create project tracking systems for strategic initiatives
• Support implementation of Cherry Bekaert recommendations
• Improve communication and accountability across management teams
• Reduce executive administrative burden and improve organizational efficiency

This role offers direct exposure to executive leadership, business operations, healthcare services, transportation logistics, insurance operations, acquisitions, and strategic growth initiatives.

For the right candidate, there is significant opportunity to grow into senior operations, Chief of Staff, or leadership roles as the organization continues to expand.

Please submit:

1. Resume
2. Cover Letter
3. A 2–3 minute video introducing yourself and answering:

• Why are you interested in this role?
• Tell us about a project or system you successfully implemented.
• Why do you believe you would thrive in a fast-paced entrepreneurial environment?

We are looking for someone who loves bringing order to complexity, thrives on execution, and wants to play a meaningful role in helping a growing organization reach the next level.