Operations Specialist

• Serve as the primary non-payroll point of contact for contractors
• Run scheduled 7/30/60/90-day and annual contractor check-ins
• Coordinate contractor engagement initiatives, including anniversaries, birthdays, recognition, and team moments
• Track PTO, contractor changes, and lifecycle events
• Support contractor onboarding and offboarding, including paperwork, accounts, access, and first-week experience
• Maintain independent contractor agreements, tax forms, background checks, and compliance documents
• Flag contractor concerns, morale risks, or retention signals to the CEO
• Collect and organize contractor timesheets, invoices, reimbursements, bonuses, and adjustments
• Prepare payroll and billing data for review and assist with reconciliation and discrepancy tracking
• Maintain contractor master files, billing trackers, and payment trackers
• Maintain client and hiring project trackers in Monday.com
• Track hiring milestones, interviews, feedback, offers, and start dates
• Monitor outstanding client and internal action items and flag stalled or overdue work
• Coordinate scheduling, documentation, and follow-ups
• Support client onboarding, post-placement workflows, and recurring client reporting
• Maintain Monday.com boards, Google Sheets, Workable, and reporting dashboards
• Organize shared Google Drive files and ensure consistency across systems
• Identify duplicate, missing, outdated, or inconsistent information
• Assist with data cleanup and system migrations
• Maintain templates, checklists, SOPs, and operational documentation
• Prepare recurring operational reports and update dashboards and KPI trackers
• Compile information across systems, prepare meeting agendas, and follow up on action items
• Test new workflows, recommend practical improvements, and support special projects

• 3+ years in Operations, Business Administration, HR Operations, Recruitment Operations, or Customer Operations
• Strong organizational and follow-through skills
• Strong spreadsheet and data-management skills
• Excellent attention to detail
• Comfortable working across multiple systems and managing recurring deadlines independently in a fast-paced remote environment
• Strong problem-solving and critical-thinking skills
• Strong written English and professional communication
• High integrity and discretion with financial and personal data
• Warm and people-oriented in contractor interactions
• Preferred: experience supporting a U.S.-based company, startup, or professional services firm
• Preferred: experience with contractor engagement, HR administration, or people operations
• Preferred: experience with Monday.com, Google Sheets, Workable, HubSpot, QuickBooks, Xero, Wise, or Stripe
• Preferred: experience supporting payroll, billing, recruiting, HR, or contractor operations
• Preferred: experience creating or maintaining SOPs and using automation/AI tools such as Zapier, Make, or Google Apps Script

• Competitive compensation package
• Regular payday in USD twice per month
• Work remotely, forever, from home wherever that is in the world
• Milestone gifts and birthday treats
• Team offsites, meetups, virtual town halls, and international paid travel
• Supportive global networking community
• Mentorship, advocacy, and support
• Promotions, raises, and scope increases