We are seeking an efficient and detail-oriented Tax Form Annotation Specialist. This hybrid role requires both hands-on experience with tax documentation and the technical expertise to annotate forms in Label Studio or any other software. You will use tax forms to extract bounding box information with correct relationships between the boxes.
Core Workflow & ResponsibilitiesThe role follows a structured six-step pipeline:
Phase 1 — Research
Form Research: Study tax form layouts, field relationships, and IRS/Financial institutions/local authority instructions to establish annotation scope and rules.
Phase 2 — Drawing Bounding Boxes
Define Field Keys & Schema: Create Labels, Fields, and Data Types in Label Studio for every identifiable field on the form.
Draw Bounding Boxes: Precisely draw bounding boxes over each field and assign the correct Label, Field name, and Data Type to every box.
Phase 3 — Relationships
Define Inter-field Edges: Identify intercorrelated fields and configure relationship tags and edge links between them in Label Studio.
For calculation relations, provide formula in a separate sheet to be used in Phase 4
Phase 4 — Post-Processing
Export, Test & Validate: Generate JSON and YAML annotation exports, test overlay alignment on source PDFs, and verify schema integrity.
Tax & Domain Knowledge
Solid understanding of tax form structures (e.g. W-2, 1040, 1099, VAT returns, Self-Assessment, corporate tax schedules)
Familiarity with field dependencies within tax forms — relationships between income lines, deductions, credits, and totals
Working knowledge of tax authority form-filling guidelines (IRS, Financial institutions, or equivalent)
Ability to research and interpret unfamiliar form types independently
Annotation & Technical Skills
Hands-on experience with Label Studio or a comparable document annotation platform
Proficiency in drawing precise bounding boxes and applying structured label schemas
Understanding of field-level data types: strings, dates, currency, checkboxes, enumerations
Ability to define and document field metadata including format constraints and validation rules
Familiarity with JSON and YAML for reviewing and validating annotation exports
Experience linking related fields using relationship/edge tagging
Background in accounting, bookkeeping, or tax preparation
Experience with bounding boxes and label studio or similar
Prior work on training data for document AI
Bounding boxes are accurate, consistent, and cover all meaningful fields on every form
Field keys and schemas are correctly defined and follow agreed naming conventions
Metadata is complete and correct for every annotated field
Exported JSON/YAML overlays cleanly on source PDFs with no misalignment
Inter-field relationships are logically mapped and documented
Adapting to changing requirements in a fast paced work environment
Full-time. 40 hours/week (30 hours/week is exceptionally acceptable, but 20 hours/week is not). 4 hours overlap with PST
LocationBangladesh, Brazil, Colombia, Egypt, Ghana, India, Indonesia, Philippines, Sri Lanka, Turkey, United States, Vietnam.
Skills Required
- Solid understanding of tax form structures (W-2, 1040, 1099, VAT, Self-Assessment, corporate tax schedules)
- Familiarity with field dependencies within tax forms (income lines, deductions, credits, totals)
- Working knowledge of tax authority form-filling guidelines (IRS, financial institutions, or equivalents)
- Ability to research and interpret unfamiliar form types independently
- Hands-on experience with Label Studio or comparable document annotation platform
- Proficiency in drawing precise bounding boxes and applying structured label schemas
- Understanding of field-level data types: strings, dates, currency, checkboxes, enumerations
- Ability to define and document field metadata including format constraints and validation rules
- Familiarity with JSON and YAML for reviewing and validating annotation exports
- Experience linking related fields using relationship/edge tagging
- Full-time availability (40 hours/week; 30 hours/week exceptionally acceptable) with 4 hours overlap with PST
- Background in accounting, bookkeeping, or tax preparation
- Prior work on training data for document AI
- Experience with bounding boxes and Label Studio or similar (listed as nice-to-have)
What We Do
Careerflow.ai is an AI-powered career management platform and 'career copilot' dedicated to helping job seekers land their dream jobs. The company provides a comprehensive end-to-end toolkit featuring an AI resume builder, LinkedIn profile optimizer, and job tracking tools. By streamlining the application process and optimizing professional profiles, Careerflow helps users navigate the competitive job market and get hired at top tech and startup companies faster.







