Project Management migration

Migrate from TeamWork Live to Jira

Field-level mapping, validation, and rollback between TeamWork Live and Jira. We move data and schema; workflows are rebuilt natively in Jira.

TeamWork Live logo

TeamWork Live

Source

Jira

Destination

Jira logo

Compatibility

91%

10 of 11

objects map 1:1 between TeamWork Live and Jira.

Complexity

CModerate

Timeline

3-5 weeks

Rollback included Accuracy guarantee Field-level validation

Overview

What this migration involves

Moving from TeamWork Live to Jira is a structural migration that requires reconciling two fundamentally different project management paradigms. TeamWork Live organizes work around Projects containing Task Lists with ordered tasks, client access controls, and built-in time tracking for billing workflows. Jira organizes work around Projects containing Issues with configurable issue types (Story, Task, Bug, Epic), sprint-based agile boards, and worklog-based time tracking. We map TeamWork Live Projects directly to Jira Projects, Task Lists to Jira Components or Labels depending on their usage pattern, and individual Tasks to Jira Issues. Milestone dates from TeamWork Live become Jira Fix Versions with the milestone name and target date preserved. Custom fields (text, number, dropdown) migrate to Jira custom fields, but dropdown option lists must be recreated in Jira's field configuration before import. Time entries present the most significant schema gap: TeamWork Live time entries are billing-oriented with billable/non-billable flags, while Jira worklogs track time against issues without a native billing flag. We preserve the time entry payload and flag the billing field for manual mapping or a post-migration custom field. We do not migrate TeamWork Live task-ordering sequences as Jira does not expose a position index API field; we instead write a script to apply rank-based sorting on ingest or document the manual reorder requirement.

Field-level fidelity

Every standard and custom field arrives verified.

Schema-aware mapping

AI proposes the map; you confirm before any record moves.

Relationships preserved

Parent–child, lookups, and ownership stay linked.

Full activity history

Calls, emails, meetings — with original timestamps.

Attachments & notes

Documents, uploads, and inline notes move with the record.

Why teams make this switch

Two sides of the same decision

Leaving

TeamWork Live logo

TeamWork Live

What's pushing teams away

  • The user interface is described as dated and clunky, with slower loading times compared to modern PM tools.
  • Task visibility and change-tracking are weaker than competing platforms, making it harder to keep teams aligned on updates.
  • Steep onboarding and learning curve frustrate new users who expect a more intuitive initial experience.
  • Limited reporting depth and integration options restrict the platform's usefulness for data-driven organizations.
  • Teams outgrow the feature set and migrate to tools like Smartsheet, Asana, or Monday for more flexible automation and views.

Choosing

Jira logo

Jira

What's pulling them in

  • Industry-standard tool with deep Git integration and sprint reporting that engineering teams already know, reducing onboarding friction for new hires.
  • Highly customizable workflows and status schemes let business teams model complex approval chains without writing code.
  • Strong ecosystem of Atlassian Marketplace apps means specialized capabilities like time tracking or portfolio management are one install away.
  • Free tier with up to 10 users and unlimited issues gives small teams a no-cost entry point to validate the platform before committing budget.
  • Visibility features — boards, backlog grooming, sprint reports, and dashboards — give leadership a shared view of what is planned, in progress, blocked, and done.

Object mapping

How TeamWork Live objects map to Jira

Each row shows how a TeamWork Live object lands in Jira, including any object-level transformations, lookup resolution, or schema-design dependencies.

Typical mapping — final map is confirmed during the sample migration step.

TeamWork Live

Project

maps to

Jira

Project

1:1
Fully supported

TeamWork Live Projects map directly to Jira Projects. The project name, description, status (active/archived), start date, and due date migrate as Project metadata. Project-level client linkage from TeamWork Live does not have a direct Jira equivalent; we map client-linked projects to Jira Projects with a label identifying the client, or recommend Jira Service Management for client-facing project management use cases. Project key (the Jira project prefix) is auto-generated or customer-specified during provisioning.

TeamWork Live

Task

maps to

Jira

Issue (Story, Task, Bug)

1:1
Fully supported

TeamWork Live Tasks map to Jira Issues with the issue type determined during scoping. Tasks marked as bugs or defects in TeamWork Live map to Jira Bug issue type. Standard work tasks map to Jira Task. Tasks representing deliverable work items from an agile backlog map to Jira Story. The task title, description, status, priority, assignee, and due date migrate directly. Jira's Assignee field resolves to the User mapped from TeamWork Live by email match.

TeamWork Live

Task List

maps to

Jira

Component

1:1
Fully supported

TeamWork Live Task Lists within a Project map to Jira Components. Component names preserve the Task List name. Components provide a grouping mechanism in Jira that mirrors Task List organization. If Task Lists are used for categorization rather than grouping (for example, tagging tasks by work type), we may instead map Task List names to Jira Labels. The customer chooses the grouping strategy during scoping based on how Task Lists are used in the source account.

TeamWork Live

Milestone

maps to

Jira

Fix Version

1:1
Fully supported

TeamWork Live Milestones map to Jira Fix Versions with the milestone name as the version name and the target date as the release date. TeamWork Live milestones that have an associated completion date are flagged separately; we create a corresponding Fix Version with a released status in Jira. Milestones without a due date are created as unreleased versions. The project association maps directly.

TeamWork Live

User

maps to

Jira

User

1:1
Fully supported

TeamWork Live Users map to Jira Users by email address as the deduplication key. Active and inactive status is preserved. Guest or client-level users from TeamWork Live are held in a reconciliation queue because Jira Software does not have a native guest user concept at the project level; these users may require manual provisioning or a separate Jira Service Management customer account if client access is required in the destination.

TeamWork Live

Time Entry

maps to

Jira

Worklog

1:1
Fully supported

TeamWork Live Time Entries map to Jira Issue Worklogs with the hours logged, date, and optional notes preserved. The primary schema gap is the billable/non-billable flag: TeamWork Live marks time entries as billable for client invoicing, but Jira worklogs have no native billing flag. We preserve the billable flag value in a custom field twl_billable__c on the Jira Issue and flag it for the customer's admin to map to their invoicing workflow post-migration. Hourly rate overrides from TeamWork Live are held as a separate mapping note for the customer's finance team.

TeamWork Live

Comment

maps to

Jira

Comment

1:1
Fully supported

TeamWork Live Comments attached to tasks migrate as Jira Issue Comments with the comment text, author (resolved by email to Jira User), and timestamp preserved. Rich-text formatting in TeamWork Live comments may not round-trip cleanly; HTML-heavy comments are flagged for manual review post-migration or cleaned to plain text during import.

TeamWork Live

Custom Field (Project Level)

maps to

Jira

Custom Field

1:1
Fully supported

TeamWork Live project-level custom fields (text, number, dropdown) map to Jira Project-level custom fields. We pre-create the destination custom fields in Jira with the correct field type (text, number, select, multi-select) before migration. Dropdown option lists from TeamWork Live must be manually recreated in Jira's field configuration as Jira does not support programmatic option creation via the REST API. This is documented in the migration scope as a pre-migration admin task.

TeamWork Live

Custom Field (Task Level)

maps to

Jira

Custom Field

1:1
Fully supported

TeamWork Live task-level custom fields map to Jira Issue-level custom fields with the same type mapping. Text fields become Jira Text Field (single-line) or Text Area (multi-line) depending on the expected content length. Number fields map to Jira Number Field. Dropdown fields map to Jira Select Field with options recreated in Jira field configuration. Custom field data is only available if the source TeamWork Live account is on a Premium plan or above; custom fields do not exist in lower-tier accounts.

TeamWork Live

Tag

maps to

Jira

Label

1:1
Fully supported

TeamWork Live Tags applied to tasks or projects migrate as Jira Labels. Labels are stored as string arrays and map directly to Jira's label field. Jira Labels have a 255-character limit per label; tags exceeding this limit are truncated or flagged for renaming. Jira Labels do not support hierarchical tagging, so any tag categorization logic from TeamWork Live must be redesigned in Jira using components or custom fields.

TeamWork Live

Company / Client

maps to

Jira

Project Label or Component

lossy
Fully supported

TeamWork Live Companies linked to projects for client access and billing tracking do not have a direct Jira equivalent in Jira Software. We map company names to Jira Project Labels with a client: prefix, or recommend Jira Service Management if the client-facing project management use case is central to the migration. Project-level client permissions from TeamWork Live cannot migrate to Jira Software's permission scheme without redesign; we document the current permission structure as a written inventory for the customer's admin to rebuild.

Gotchas + challenges

What specifically takes care here

Platform-specific issues from each side, plus the pair-specific challenges that don't show up on either platform's page on its own.

TeamWork Live logo

TeamWork Live gotchas

Medium

Task ordering is not a first-class API field

High

Custom fields gated behind paid tiers

Medium

No bulk export endpoint for time entries

Jira logo

Jira gotchas

High

Unsupported workflow validators silently skipped during migration

High

Custom fields converted to flat text labels when migrating to non-Jira platforms

Medium

Historical status-change timestamps lost when exporting without a Marketplace plugin

Medium

Attachment import failures from oversized files and JQL reference corruption

Medium

Points-based API rate limits enforced on Jira Cloud apps from March 2026

Pair-specific challenges

  • Task ordering is not preserved across the migration

    TeamWork Live Task Lists maintain an ordered sequence of tasks, but the API does not expose a position or ordering index as a discrete field. We retrieve tasks by list and preserve their original sequence in the migration payload, but Jira does not have a native position field API for ordering issues within a board or backlog. We write a rank-based sort script to apply ordering on ingest, but the customer should verify the ordering in a Jira test environment before production cutover. If the destination Jira project uses ranking (Issue Rank field in Jira Software Premium), we map the sequence to that field; otherwise, ordering requires manual adjustment in the Jira backlog or board view.

  • Custom fields gated behind TeamWork Live paid tiers

    TeamWork Live custom fields are only available on the per-user Premium subscription plan and above. If the source TeamWork Live account is on a lower tier, no custom field definitions or values will exist in the API response. We detect this at scan time and flag missing custom field data before presenting the migration scope. If custom fields are present, their dropdown option lists must be manually recreated in Jira's field configuration before import; Jira does not support programmatic option creation via REST API. We deliver a written list of all dropdown options requiring manual entry as part of the pre-migration admin checklist.

  • Time entry billing flags have no Jira equivalent

    TeamWork Live time entries carry billable/non-billable flags used for client invoicing. Jira worklogs track time spent on issues but have no native billing flag. We preserve the billable flag in a custom field twl_billable__c on the Jira Issue and document the mapping for the customer's finance or admin team. If the customer relies on TeamWork Live's time tracking for billing, they must configure an invoicing workflow post-migration, either using Jira's custom field or a third-party time-tracking integration. This is a process gap, not a data loss issue, but it requires planning before go-live.

  • Client-level access permissions do not migrate

    TeamWork Live supports per-project client access controls allowing external stakeholders to view relevant work without internal credentials. Jira Software does not have a comparable guest-level project access model. If client collaboration is required in the destination, Jira Service Management is the appropriate product, not Jira Software. We flag this gap during scoping and recommend Jira Service Management for any migration where client-facing project visibility is a core requirement. For internal-only migrations, we document the current permission structure in a written inventory for the customer's admin to rebuild in Jira's permission scheme.

  • No bulk export endpoint for time entries

    TeamWork Live time entries must be retrieved individually or in small batches via the standard API. For accounts with thousands of logged hours, iterating through time entries sequentially can hit rate limits. We apply chunked retrieval with exponential backoff and retry logic to avoid missing time entry records during export. For very large time entry volumes (over 50,000 entries), we may recommend a staged migration approach where the most recent 12 months migrate first and historical entries migrate in a second pass to manage rate-limit risk.

Migration approach

Six steps for a successful TeamWork Live to Jira data migration

  1. Discovery and scope definition

    We audit the source TeamWork Live account across subscription tier (to confirm custom field availability), project count, task count, milestone count, user count (including guest/client users), time entry volume, and any tag or custom field usage. We pair this with a Jira edition review: Jira Software Standard ($7.75/user/month) covers basic issue tracking and agile boards; Jira Software Premium ($15.50/user/month) adds advanced roadmaps, portfolio management, and issue ranking. The discovery output is a written migration scope covering record counts, custom field inventory, time entry volume, and a Jira edition recommendation.

  2. Jira project provisioning and schema design

    We provision Jira Projects matching the TeamWork Live project structure, including the Jira project key (prefix), name, project lead, and default issue type scheme. We design the issue type scheme: Tasks map to Stories, Tasks, or Bugs depending on how they are categorized in TeamWork Live. We pre-create custom fields with matching types, recreate dropdown option lists (as a documented manual step), and configure Fix Versions for each TeamWork Live Milestone. Components are provisioned per Task List if the grouping strategy is chosen. Schema is deployed to a Jira Sandbox or the production instance before data import begins.

  3. User reconciliation and provisioning

    We extract every distinct TeamWork Live User (internal team members and guest/client users) referenced on projects, tasks, comments, and time entries. Internal users are matched by email to existing Jira Users. Guest or client users are held in a reconciliation queue because Jira Software does not support project-level guest access; we document these users and recommend Jira Service Management for client-facing use cases, or manual provisioning if client access is not required. Any TeamWork Live user without a matching Jira User is flagged for the customer's admin to provision before record import resumes.

  4. Sandbox migration and mapping validation

    We run a full migration into the Jira destination using a representative data sample (all projects, 10-20% of tasks and time entries, all milestones, all users). The customer's project lead reconciles record counts (Projects in, Issues in, Versions in, Worklogs in, Comments in), spot-checks 25-50 random issues against the TeamWork Live source, and verifies milestone dates, custom field values, and time entry hours. Mapping corrections (issue type assignments, component naming, custom field type adjustments) happen in the sandbox validation phase, not in production. The customer signs off the mapping before production migration begins.

  5. Production migration in dependency order

    We run production migration in record-dependency order: Jira Projects first, then Fix Versions (from Milestones), then Components (from Task Lists), then Users (validated against the reconciliation queue), then Issues (with assignee and component resolution), then Comments, then Worklogs via Jira REST API with chunked batching and exponential backoff. Custom fields migrate as part of the Issue payload. Tags migrate as Labels on each Issue. Each phase emits a row-count reconciliation report before the next phase begins.

  6. Cutover, delta sync, and permission rebuild handoff

    We freeze TeamWork Live writes during cutover, run a final delta migration of any tasks, comments, or time entries modified during the migration window, then enable Jira as the system of record. We deliver the written permission inventory documenting TeamWork Live project-level access controls for the customer's admin to rebuild in Jira's permission scheme. We support a one-week hypercare window where we resolve any reconciliation issues raised by the customer's team. We do not rebuild TeamWork Live automations, forms, or reports as Jira configurations; those are delivered as written inventories for the customer's admin or a Jira partner to rebuild post-migration.

Platform deep dives

Context on both ends of the pair

TeamWork Live logo

TeamWork Live

Source

Strengths

  • REST API provides programmatic access to projects, tasks, users, and time entries for integrations.
  • Task-level custom fields (text, number, dropdown) are supported and accessible via the API.
  • Time tracking is built in and linked to tasks, making billable-hour workflows possible.
  • Per-project client access controls allow external stakeholders to view relevant work without internal credentials.

Weaknesses

  • Interface is widely considered outdated with slower performance and less polished UX than newer PM tools.
  • Limited automation capabilities compared to platforms like Asana or Monday, restricting workflow sophistication.
  • Reporting and dashboard features are basic, with minimal customisation options for analytics.
  • Sparse third-party integration ecosystem beyond the REST API, limiting native connectivity with CRMs and finance tools.
Jira logo

Jira

Destination

Strengths

  • Deeply customizable workflows and status schemes with no hard limits on workflow complexity or number of custom statuses.
  • Strong agile ceremony support: sprint planning, backlog grooming, velocity tracking, and burndown charts for Scrum teams.
  • Industry-standard developer tool with native Git integration linking commits, pull requests, and deployments to issues.
  • Large Atlassian Marketplace with thousands of plugins extending time tracking, portfolio management, and reporting capabilities.
  • Free tier available for up to 10 users with unlimited issues, enabling evaluation before committing to a paid plan.

Weaknesses

  • Excessive configurability creates a steep learning curve; cross-team consistency is hard to maintain without strict governance.
  • Performance degrades with large backlogs, complex custom fields, and heavily nested issue hierarchies.
  • Reporting requires additional configuration or paid plugins; out-of-the-box analytics are limited for business users.
  • Jira lacks native sprint management, requiring Jira Software for true agile team features.
  • Teams outside engineering resist adoption due to UI complexity, leaving the all-in-one promise unfulfilled for cross-functional organizations.

Complexity grading

How hard is this migration?

Moderate Project Management migration. 4 of 8 objects need a mapping; the rest are 1:1.

C

Overall complexity

Moderate migration

Derived from compatibility, mapping clarity, API constraints, and data volume across TeamWork Live and Jira.

  • Object compatibility

    C

    4 of 8 objects need a mapping; the rest are 1:1.

  • Field mapping clarity

    C

    Field mapping is derived from defaults — final spec confirmed during the sample migration.

  • Timeline complexity

    B

    8-object category — typical timelines run 2–7 days end-to-end.

  • API constraints

    B

    TeamWork Live: 6,000 requests per hour per user account. Exceeding the limit returns 503 Service Unavailable with a Retry-After header indicating when to resume. Higher limits available on request to [email protected]..

  • Data volume sensitivity

    B

    TeamWork Live doesn't expose a bulk API — REST + parallelization used for high-volume runs.

Estimator

Estimate your TeamWork Live to Jira migration cost

Rule-based pricing — no per-record fees, no manual quotes. Migrations over 2M records are scoped individually.

Step 1

What are you migrating?

Pick a category, then your source and destination platforms.

Category

FAQ

Frequently asked questions about TeamWork Live to Jira data migrations

Answers to the questions buyers ask most during TeamWork Live to Jira migration scoping. Not seeing yours? Book a call.

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Most migrations land between three and five weeks for accounts under 5,000 tasks and 50 projects with no custom fields and moderate time entry volume. Migrations with custom fields, milestone-heavy project structures, large time entry histories (over 10,000 entries), or multiple Task Lists requiring component-based reorganization move to six to ten weeks because of Jira schema provisioning, custom field recreation, milestone-to-Fix-Version transformation, and time entry reconciliation.

Adjacent paths

Related migrations to explore

Ready when you are

Move from TeamWork Live.
Land in Jira, intact.

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