Senior Manager, Machine Learning (Data Operations)

About us Coalition is the world's first Active Insurance provider designed to help prevent digital risk before it strikes. Founded in 2017, Coalition combines comprehensive insurance coverage and innovative cybersecurity tools to help businesses manage and mitigate potential cyberattacks. Opportunities to make an impact with bold thinking are real—and happening daily at Coalition. About the role Coalition's machine learning models are only as good as the data they're trained on. This role exists to make sure that data is right. You'll own labeling quality and methodology across Coalition — designing annotation tasks, defining quality frameworks, and ensuring every labeled dataset meets the standard required to ship production ML models. You'll manage our labeling platform (Label Studio), work directly with ML and product teams to structure labeling programs, and oversee outsourced labeling vendors to hit quality and throughput targets. This role reports to the Chief Product Officer and sits at the intersection of product, ML, and operations. You won't manage internal labelers — all annotation work is outsourced — but you will be the single point of accountability for whether Coalition's labeled data is accurate, consistent, and fit for purpose. Responsibilities • Labeling quality & methodology: Define annotation guidelines, taxonomies, and edge-case protocols for each labeling program. Establish gold standard datasets, inter-annotator agreement (IAA) targets, and audit sampling processes. Identify and remediate mislabeled data in existing datasets. • Platform & tooling: Serve as the primary user and requirements driver for Label Studio — defining project configuration needs, workflow designs, pre-labeling pipeline requirements, and integration points with ML infrastructure. Partner with the data engineering team that builds and maintains the platform. • Cross-functional partnership: Work with ML engineers, data scientists, and product managers to translate model requirements into well-structured labeling tasks. Challenge teams on task design when labeling instructions are ambiguous or likely to produce unreliable labels. • Vendor management: Source, onboard, and manage external labeling vendors and BPOs in coordination with Coalition's operations team. Set quality SLAs, run calibration sessions, and manage feedback loops to labelers. Hold vendors accountable to accuracy, not just throughput. • Measurement & improvement: Define and track operational metrics — label accuracy, IAA scores, cost per label, turnaround time — and use them to drive continuous improvement. Identify opportunities for active learning, model-assisted labeling, and pre-annotation to reduce cost without sacrificing quality. Skills and Qualifications • 5+ years in ML data operations, data labeling, or a related field (ML engineering, data science, or data engineering with heavy labeling exposure) • Deep understanding of annotation quality frameworks: IAA, consensus labeling, gold standard evaluation, error taxonomy, and calibration workflows • Direct experience managing labeling platforms (Label Studio strongly preferred; Scale AI, Labelbox, Prodigy, or similar acceptable) • Track record managing outsourced labeling vendors or BPOs for ML data production • Familiarity with common ML labeling tasks: text classification, NER, document extraction, intent detection • Comfortable working in Python and SQL; bonus if you've built tooling around labeling workflows or quality measurement • Strong opinions on what makes labeled data good or bad, and the willingness to push back when it's bad • Experience in insurance, cybersecurity, or fintech is a plus but not required Compensation As a remote-first organization, our compensation reflects the cost of labor across several Canadian geographic markets. In Alberta, British Columbia & Ontario the base salary for this position ranges from $136,800/year up to $186,800/year. For all other locations, the base salary for this position ranges from $123,100/year up to $153,900/year. Consistent with applicable laws, an employee's pay within this range is based on a number of factors, which include but are not limited to relevant education, skills, job-related knowledge, qualifications, work experience, credentials, and/or geographic location. Your Recruiter can share more on the specific target salary range for your location during the interview process. Coalition, Inc. reserves the right to modify this range as needed. Vacancy Status: This posting is for an existing vacancy. Use of AI: We utilize AI-assisted tools to help us organize and review the high volume of applications we receive. However, our human recruiting team makes all final hiring decisions and interview selections, valuing personal connection over algorithms. Application Updates: Consistent with our commitment to transparency, if you are interviewed for this role, we will provide a status update on your application within 45 days of your final interview. Perks • 100% medical, dental, and vision coverage • Flexible PTO • Annual home office stipend and WeWork access • Mental & physical health wellness programs like Headspace, Lumino, and more! • Competitive compensation and opportunity for advancement Why Coalition? Work at Coalition is centered on the joint mission to Protect the Unprotected. We have built a remote-first, highly inclusive culture that welcomes people from diverse backgrounds. We trust each other to take responsibility, share ownership of outcomes, and put in the work together to protect businesses from digital risk. Coalition’s exceptional growth stems from its ability to address real-world problems for organizations of all sizes while remaining true to our founding values of character, humility, responsibility, purpose, authenticity, and inclusion. We’re always looking for collaborative, inquisitive individuals to join #OurCoalition. Visit our Newsroom > Privacy Notice Coalition is committed to protecting your privacy and handling your personal information responsibly. We collect, use, and store personal information as necessary for the recruitment process and in compliance with applicable privacy laws and regulations in all regions where we operate. We want you to understand what personal information we collect, how we use it, and your rights regarding access, correction, and deletion of your data where applicable. Information submitted, collected, and processed as part of your application is subject to Coalition's Privacy Policy. For further details, please review our full Privacy Policy or contact us with any questions regarding how your information is handled. Our Privacy Policy > Safe Hiring Notice All legitimate communication from Coalition comes from @coalitioninc.com emails, and open roles are listed only on our Careers page. We never ask for payment, banking details, or personal identification before an offer is accepted through our secure systems. If you believe you’ve been a victim of fraudulent recruiting, follow guidance from the Federal Trade Commission (FTC). Anti-Discrimination Notice Coalition is proud to be an Equal Opportunity employer. Our policy is to provide equal employment opportunities to all individuals, without discrimination or harassment on the basis of any characteristic protected by applicable laws in each country where we operate. This commitment includes, but is not limited to, ensuring equal treatment in recruitment, selection, training, promotion, transfer, compensation, and all other aspects of employment. Coalition does not tolerate discrimination or harassment of any kind, and we are dedicated to fostering an inclusive and supportive workplace. Accommodations Coalition is committed to providing reasonable accommodations to qualified individuals with disabilities, including applicants and employees, in accordance with applicable laws and regulations in each country where we operate. Our policy is to support equal opportunity in the hiring process by considering qualified applicants regardless of disability or other protected characteristics, unless providing accommodation would impose an undue hardship or disproportionate burden. If you require accommodation to complete an application, interview, pre-employment testing, or participate in the selection process, please contact us at candidateaccommodations@coalitioninc.com. We also consider all qualified applicants, including those with criminal histories, in line with applicable laws and regulations in each jurisdiction. To all recruitment agencies: Coalition does not accept unsolicited agency resumes. Do not forward resumes to our email alias, employees, or other physical or virtual organization locations. Coalition is not responsible for any fees related to unsolicited resumes.