Annotation Operations Manager – Remote Team Leadership (Contract)

Lead a team of 20-40 remote annotators building speech datasets for next-generation AI We're scaling our audio annotation operations and need an experienced team manager to oversee daily operations, quality control, and training for our growing freelancer workforce. You'll be the operational backbone ensuring our transcription projects deliver consistent, high-quality results while hitting ambitious volume targets. What You'll Own Daily Team Leadership & Management Manage 20-40 remote freelance annotators across multiple concurrent audio transcription projects Monitor individual and team performance across Data Plus, Label Studio, and SuperAnnotate platforms Handle escalations, resolve workflow bottlenecks, and maintain team morale Coordinate assignment distribution and workload balancing across annotators Training Program Development Design and deliver comprehensive onboarding programs for new annotators Create training materials for Data Plus, Label Studio, and SuperAnnotate platform usage and transcription guidelines Conduct regular calibration sessions to maintain quality standards Develop skill-building workshops for complex annotation scenarios Quality Assurance Operations Manage QA team members who review annotator submissions Establish and maintain quality control processes and sampling strategies Analyze quality metrics and implement improvement initiatives Handle quality escalations and corrective action plans Platform Operations & Assignment Management Monitor daily progress and assignment completion across Data Plus, Label Studio, and SuperAnnotate Manage task distribution and deadline tracking across all platforms and active projects Troubleshoot platform-specific issues and coordinate with technical support teams Optimize workflow processes across platforms to maximize efficiency and output Performance Reporting & Analytics Generate weekly KPI reports covering hours annotated, quality percentages, and productivity metrics Track team performance against targets and identify improvement opportunities Present operational updates and recommendations to senior management Maintain detailed records of team performance and project outcomes Ready to lead the team building tomorrow's AI speech capabilities? This is a remote contract position requiring immediate availability. What You Bring to the Role Essential Leadership Experience 2+ years managing annotation or transcription teams (minimum requirement) Proven track record leading remote freelancer workforces (15+ people) Experience with quality control processes in linguistic or content annotation projects Success meeting aggressive volume and quality targets with distributed teams Annotation Industry Knowledge Deep understanding of audio transcription workflows and quality standards Experience with multiple annotation platforms (Data Plus, Label Studio, SuperAnnotate, or similar), workflow management, and QA processes Knowledge of linguistic annotation challenges (stutters, overlaps, accents, etc.) Familiarity with speech dataset requirements for AI training Operational Excellence Strong project management skills with ability to juggle multiple concurrent projects Experience developing training programs and documentation for technical processes Data-driven approach to performance management and process optimization Excellent problem-solving skills for workflow bottlenecks and quality issues Communication & Leadership Outstanding written English with ability to create clear training materials Experience providing feedback and coaching to improve individual performance Comfortable presenting metrics and recommendations to senior management Strong interpersonal skills for managing remote, multicultural teams Technical Readiness Comfortable learning and managing multiple annotation platforms and workflow tools Experience with cross-platform performance tracking, reporting, and basic data analysis Reliable home office setup for managing distributed teams Available during core business hours with flexibility for global team coordination