Executive Operations Assistant to CEO

Executive Operations Assistant to CEORed Crow Holdings?? Raleigh, NC (In-Office Preferred)?? Salary: $65,000 - $85,000 + Performance Bonus OpportunitiesHelp Build a Multi-Company Organization from the Ground UpRed 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.Companies You'll SupportPinnacle Freight SolutionsRed Crow ManagementHeavenly Sent Home Care ServicesAffluent Logistics & TransportationAlpha & Omega Insurance GroupWhat You'll Be Responsible ForExecutive Operations & Project CoordinationManage and coordinate strategic initiatives across multiple companiesTrack project deadlines, deliverables, and implementation timelinesFollow up with managers to ensure accountability and executionCoordinate cross-company projects and prioritiesPrepare executive meeting agendas, notes, and action plansMaintain executive project trackers and implementation dashboardsKPI Reporting & Executive DashboardsCollect weekly KPIs from company managersMaintain executive dashboards and scorecardsTrack performance metrics across all businessesIdentify missing data, reporting gaps, and operational bottlenecksPrepare weekly executive summary reportsSupport decision-making through accurate reporting and analysisCherry Bekaert & Strategic Initiative ImplementationCoordinate implementation of recommendations from consultants, advisors, accountants, and legal partnersMaintain project plans and implementation timelinesTrack action items and ensure follow-throughGather supporting documentation for financial and operational initiativesProvide progress updates directly to the CEOCompliance, Certifications & LicensingTrack company certifications, licenses, renewals, and compliance requirementsMaintain compliance calendarsCoordinate documentation submissionsSupport audits, credentialing, and regulatory requestsEnsure critical deadlines are not missedExecutive SupportManage CEO calendar and schedulingCoordinate meetings and appointmentsOrganize executive communicationsTrack follow-up items and commitmentsAssist with travel arrangements and meeting logisticsMaintain organized company files and documentationSystems & Process ImprovementAssist with SOP development and documentationHelp implement process improvements and automation initiativesSupport CRM, ClickUp, Google Workspace, and operational systemsMaintain organizational structure and documentation standardsIdeal CandidateYou 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 businessesPreferred Qualifications3+ years supporting executives, founders, or business ownersExperience in project management, operations coordination, or executive administrationStrong Google Workspace and Microsoft Office skillsExperience with ClickUp, Asana, , Airtable, or similar platformsExperience building dashboards and KPI reporting systemsExperience coordinating multiple projects simultaneouslyHealthcare, transportation, insurance, accounting, compliance, or multi-company experience preferredPreferred Certifications (Not Required)PMP (Project Management Professional)CAPM (Certified Associate in Project Management)Lean Six SigmaScrum Master CertificationGoogle Project Management CertificationSuccess in the First 90 DaysThe successful candidate will:Implement a company-wide KPI reporting processEstablish executive dashboards and scorecardsOrganize compliance and certification tracking systemsCreate project tracking systems for strategic initiativesSupport implementation of Cherry Bekaert recommendationsImprove communication and accountability across management teamsReduce executive administrative burden and improve organizational efficiencyGrowth OpportunityThis 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.To ApplyPlease submit:ResumeCover LetterA 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.