Project Management migration

Migrate from TeamWork Live to Trello

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

TeamWork Live logo

TeamWork Live

Source

Trello

Destination

Trello logo

Compatibility

92%

11 of 12

objects map 1:1 between TeamWork Live and Trello.

Complexity

BStandard

Timeline

2-4 weeks

Rollback included Accuracy guarantee Field-level validation

Overview

What this migration involves

Moving from TeamWork Live to Trello is a schema translation from a hierarchical Project structure into Trello's Board-List-Card Kanban model. TeamWork Live organizes work as Projects containing Task Lists containing Tasks, with Milestones as standalone date markers; Trello uses Boards containing Lists containing Cards, where due dates and labels substitute for Milestones and task ordering lives as list position. We resolve the structural mapping during scoping: each TeamWork Live Project becomes one Trello Board, each Task List becomes a Trello List, and each Task becomes a Card. Milestones without a direct Trello equivalent are encoded as due dates on milestone-linked cards with a dedicated Label for filtering. Time entries require a separate migration step or a time-tracking Power-Up post-migration. Time entries in TeamWork Live are linked to tasks but must be moved through Trello's API or the customer enables a time-tracking Power-Up post-migration. We do not migrate Automations, Butler rules, or Power-Up configurations; we deliver a written inventory of any Power-Up dependencies requiring rebuild. Guest user permissions in TeamWork Live do not map directly to Trello Guest access, and we flag the permission gap during scoping so the customer's admin can configure Guest boards post-migration.

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

Trello logo

Trello

What's pulling them in

  • Free plan supports unlimited users and 10 boards, giving small teams full access to core Kanban functionality before any paid commitment is required.
  • The drag-and-drop board/card/Label interface requires no training, which reduces adoption friction and onboarding time across distributed teams.
  • Atlassian ecosystem integration with Jira, Confluence, and Bitbucket provides native cross-tool workflows for teams already using Atlassian tools.
  • Butler automation on paid tiers enables rule-based triggers without third-party integrations, covering basic workflow automation needs.
  • Simple visual task management with due dates, checklists, and member assignments keeps individual contributors and small teams organized without complexity.

Object mapping

How TeamWork Live objects map to Trello

Each row shows how a TeamWork Live object lands in Trello, 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

Trello

Board

1:1
Fully supported

Each TeamWork Live Project maps to one Trello Board. We migrate the project name as the Board title, project description as the Board description, start and due dates as metadata flags, and project status (active/archived) as Board archival state. Project-level custom fields migrate to the Board description or a Custom Fields Power-Up note if the Trello destination is on Standard or Premium. TeamWork Live's per-project client access controls do not map directly to Trello Guest access; we flag this permission gap and recommend board-level Guest configuration post-migration.

TeamWork Live

Task List

maps to

Trello

List

1:1
Fully supported

Each TeamWork Live Task List within a Project maps to one Trello List within the corresponding Board. The list name migrates as the List title. Task ordering within each list is preserved by computing a sequence index from the TeamWork Live API response order; since ordering is not exposed as a discrete API field, we capture the iteration order at retrieval time and apply it as card position integers during Trello card creation. Lists are created before cards in the migration sequence to satisfy Trello's list-must-exist constraint.

TeamWork Live

Task

maps to

Trello

Card

1:1
Fully supported

Each TeamWork Live Task maps to one Trello Card. Standard fields migrate directly: task title becomes card name, task description becomes card description, task status maps to a Label color (or archived card state if the destination supports archival), priority maps to a priority Label, due date migrates to card due date, and estimated time is stored as a custom field or card description note. Assignee resolution uses email match against the Trello Workspace member list; unresolved assignees are flagged in the reconciliation report for admin provisioning before the migration phase.

TeamWork Live

Milestone

maps to

Trello

Card (due date + Label)

lossy
Fully supported

TeamWork Live Milestones have no direct Trello equivalent. We encode Milestones as Cards with the milestone target date set as the card due date, a dedicated milestone Label (e.g., 'Milestone') applied, and the milestone name as the card name. Completed milestones receive an additional 'Completed' Label. Milestones without a linked task are created as standalone cards within the corresponding Board List. If the customer has milestone completion dates, those migrate as the card due date with the 'Completed' Label and the card moved to a Done list.

TeamWork Live

User and Team Member

maps to

Trello

Workspace Member

1:1
Fully supported

TeamWork Live internal users map to Trello Workspace Members by email match. Guest or client-level users in TeamWork Live do not map to standard Trello Workspace Members; they map to Trello Board-level Guests, which we configure per Board after migration. We flag any TeamWork Live user without an email (unusual but possible with imported or manually created records) and store them in the reconciliation queue with a placeholder email for admin resolution.

TeamWork Live

Time Entry

maps to

Trello

Card (description note) or External Export

1:1
Fully supported

TeamWork Live time entries are linked to Tasks and contain hours logged, date, and optional notes. Trello has no native time tracking object. We migrate time entry data as structured text appended to the corresponding Card description in a 'Time Entries' section (format: date, hours, notes). For accounts with high-volume time tracking requirements, we recommend a separate time-tracking Power-Up post-migration; we deliver a CSV export of all time entries keyed by source task ID for the customer's admin to ingest into their chosen tool. The TeamWork Live API requires sequential retrieval for time entries (no bulk endpoint), so we apply chunking and retry logic for accounts with over 1,000 entries.

TeamWork Live

Comment

maps to

Trello

Card (Comment)

1:1
Fully supported

TeamWork Live comments attached to Tasks migrate to Trello Card comments. We preserve comment text, author (resolved by email match to Trello Workspace Member), and timestamp. Rich-text formatting in TeamWork Live comments may not round-trip cleanly; HTML-heavy comments are flagged in the migration report for manual review. Comments on Projects (not attached to a specific task) migrate to the Board description or a designated 'Project Notes' card at the customer's discretion during scoping.

TeamWork Live

File and Attachment

maps to

Trello

Card (Attachment)

1:1
Fully supported

Files attached to TeamWork Live Tasks or Projects are referenced by URL in the TeamWork Live API. We retrieve attachment metadata (filename, URL, upload date, uploader) and re-upload each file to the corresponding Trello Card as a Card Attachment via the Trello API. Files that were stored in TeamWork Live's internal storage are downloaded and re-uploaded; files stored externally (Google Drive, Dropbox) are re-linked as URL attachments if the original link remains accessible. Failed uploads are logged for manual retry.

TeamWork Live

Task Custom Field

maps to

Trello

Custom Field (Power-Up)

1:1
Fully supported

TeamWork Live task-level custom fields (text, number, dropdown) migrate to Trello Custom Fields Power-Up on Standard and Premium plans. We detect at scan time whether the source account is on a Premium subscription (custom fields are gated behind Premium); if not, no custom field definitions or values exist in the API response and we flag this in the scoping report. Dropdown options in TeamWork Live must be recreated in Trello's Custom Fields Power-Up configuration before migration; we deliver the option list as a configuration reference during the pre-migration schema step.

TeamWork Live

Project Custom Field

maps to

Trello

Board (description note or Custom Field)

1:1
Fully supported

Project-level custom fields in TeamWork Live migrate to the corresponding Trello Board. For Standard and Premium Trello accounts, project custom fields become Board Custom Fields if the destination supports board-level custom fields; otherwise they are encoded as structured notes in the Board description. The customer chooses the preferred encoding during scoping. If the source TeamWork Live account is not on Premium, no project custom fields exist to migrate.

TeamWork Live

Tag and Label

maps to

Trello

Label

1:1
Fully supported

TeamWork Live tags stored as string arrays on Tasks or Projects map to Trello Labels. We migrate tag names as Label names with a default color assignment; the customer can customize label colors in Trello post-migration. If a TeamWork Live tag name conflicts with a Trello reserved label name or exceeds the label name length limit, we rename it with a suffix (e.g., '_teamwork_tag') and log the rename in the migration report.

TeamWork Live

Company and Client

maps to

Trello

Board (description) or Label

1:1
Fully supported

TeamWork Live Companies and Clients linked to Projects for access control or billing tracking do not have a direct Trello equivalent. We migrate the company name and primary contact to the Board description as structured text. If the customer relies on client-level permissions in TeamWork Live, we recommend configuring a Trello Board-level Guest for each client post-migration; we deliver a client-to-email mapping CSV during the handoff for the admin to provision Guest access.

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

Trello logo

Trello gotchas

High

Billing model uses maximum seat quantity at term midpoint

Medium

Custom Field data historically stored in pluginData

Medium

API rate limits are token-gated and can block bulk migration

Medium

Guest-to-paid seat conversion triggers on multi-board membership

Low

Automation command runs are capped per plan and overage triggers upgrade pressure

Pair-specific challenges

  • Milestones have no native Trello equivalent

    TeamWork Live Milestones are standalone date-driven markers linked to Projects. Trello has no milestone object. Without an explicit encoding strategy, milestones are lost or require manual recreation. We resolve this by encoding Milestones as Cards with the target date as the card due date and a dedicated Label for filtering. Milestones without a linked task are created as standalone Cards in a designated list. The customer must review the Milestone encoding during scoping and confirm the chosen List for milestone cards, or opt to encode them as Labels on the original milestone-linked Cards instead.

  • Task ordering requires sequence computation from iteration order

    TeamWork Live does not expose task position or ordering index as a discrete API field. We capture the iteration order of tasks within each Task List at retrieval time and compute a sequence index, but this is only as reliable as the API's returned ordering. If the TeamWork Live API returns tasks in a different order than the user's view, the migrated card sequence in Trello will not match the original. We log the sequence computation method in the migration report and recommend the customer spot-check card ordering in a sandbox migration before production cutover.

  • Trello API is fragmented but complete for migration purposes

    The Trello API is not a single cohesive endpoint surface; board creation, card creation, label assignment, and attachment upload are separate endpoints with different rate limits (up to 100 requests per second for authenticated reads, lower for writes). Community reports confirm that subtasks, comments, and attachments do not always migrate cleanly through third-party tools, with formatting distortion and media transfer failures. We handle this by using Trello's direct API endpoints with retry logic, chunking attachment uploads, and logging every failed write for manual resolution.

  • Custom Fields gated behind Trello Standard and Premium

    Trello's Custom Fields Power-Up is only available on Standard ($5/user/month) and Premium ($10/user/month) plans. Free-tier Trello accounts cannot store custom field values. If the source TeamWork Live account uses custom fields and the destination Trello account is on the Free plan, we flag this gap during scoping. The customer must upgrade to Standard or Premium before migration or accept that custom field values will be encoded in card descriptions instead of typed fields. We do not upgrade the destination account as part of migration scope.

  • Guest user permissions do not map one-to-one

    TeamWork Live supports per-project Guest and Client-level users with project-specific access controls. Trello supports Workspace Members and Board-level Guests, but Guest access is scoped to individual Boards rather than a project-level permission model. Teams using TeamWork Live's client-facing collaboration features may find that Trello's Guest model requires restructuring: each Trello Board becomes a client boundary rather than each Project. We deliver a client-to-Board mapping as part of the migration handoff and flag any Teams whose clients have cross-project access that cannot be replicated in Trello without multiple Guest accounts.

Migration approach

Six steps for a successful TeamWork Live to Trello data migration

  1. Discovery and plan selection

    We audit the source TeamWork Live account across plan tier (to detect Premium-only custom fields), project count, task list count, task count, milestone count, time entry volume, comment volume, attachment count, and active user count including Guests. We pair this with a Trello plan assessment to confirm whether Standard or Premium is required for custom field migration. The discovery output is a written migration scope, a Project-to-Board mapping table, a Milestone encoding decision sheet, and a time entry migration recommendation (card notes or CSV export).

  2. Schema pre-configuration in Trello

    We provision Trello Boards for each TeamWork Live Project before any record migration. We create the required Lists within each Board (mirroring the Task Lists), configure Labels including the Milestone Label if the encoding strategy uses Labels, and apply Custom Fields Power-Up configurations if the destination is on Standard or Premium. We also configure Board-level Guest access for any TeamWork Live client contacts at this stage if the customer has chosen the per-Board Guest model.

  3. Sandbox migration and reconciliation

    We run a full migration into a Trello Workspace using representative data volume. The customer's project manager reconciles record counts (Boards in, Lists in, Cards in), spot-checks card ordering within a sample of Lists, verifies milestone encoding, and reviews time entry encoding. The customer signs off the schema and mapping before production migration begins. Any ordering issues, custom field gaps, or milestone encoding corrections happen here, not in production.

  4. Owner and user reconciliation

    We extract every distinct TeamWork Live user (internal team members and Guests) referenced on Tasks, Projects, and Comments. We match internal team members by email against the Trello Workspace member list. Guests without a matching Trello user are held in a reconciliation queue and mapped to Board-level Guest access for the customer's admin to provision after migration. User provisioning cannot proceed past this step because card assignees require valid Trello user IDs.

  5. Production migration in dependency order

    We run production migration in record-dependency order: Trello Workspace Members and Guests (validated by admin), Boards (one per Project), Lists (one per Task List within each Board), Cards with standard fields and assignee (with task sequence computed from iteration order), Milestone Cards or Label encoding, Custom Field values (if on Standard or Premium), Comments (by card), Attachments (by card, with retry on failure), Time Entries (appended to Card descriptions or exported as CSV), and Tags encoded as Labels. Each phase emits a row-count reconciliation report before the next phase begins.

  6. Cutover, validation, and Butler rebuild handoff

    We freeze TeamWork Live writes during cutover and run a final delta migration of any records modified during the migration window. We then enable Trello as the system of record. We deliver the Automation Inventory document covering any TeamWork Live task-level triggers and recommending Butler rules to replicate the behavior. We do not configure Butler rules or Power-Up installations as part of migration scope; the customer's admin or a Trello partner rebuilds automations post-migration. We support a one-week hypercare window where we resolve any reconciliation issues raised by the customer's project team.

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.
Trello logo

Trello

Destination

Strengths

  • Generous free tier with unlimited users and 10 boards, the lowest barrier to entry among major project management tools.
  • Intuitive drag-and-drop Kanban interface requires no training or onboarding documentation.
  • Deep Atlassian integration with Jira, Confluence, and Bitbucket for teams already in the ecosystem.
  • Built-in Butler automation covers rule-based triggers without requiring third-party integrations.
  • REST API with comprehensive documentation enables programmatic access to all core objects.

Weaknesses

  • Reporting and analytics are absent, with no built-in velocity tracking, burndown charts, or historical performance metrics.
  • The flat board/list/card data model scales poorly for complex projects requiring hierarchical task structures.
  • Customization is limited compared to platforms like Asana, monday.com, or Jira that offer richer field types and workflow configuration.
  • Advanced views (Timeline, Dashboard) require Premium and are not available on Standard, inflating total cost for teams needing visibility features.
  • Guest user billing rules are confusing and prone to accidental seat overages when guests join multiple boards.

Complexity grading

How hard is this migration?

Standard Project Management migration. 3 of 8 objects need a mapping; the rest are 1:1.

B

Overall complexity

Standard migration

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

  • Object compatibility

    B

    3 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 Trello 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 Trello data migrations

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

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Most migrations land between two and four weeks for accounts under 5,000 Tasks and 50 Projects with no time entry migration and no custom field complexity. Migrations with large time entry histories (over 10,000 entries), extensive milestone encoding requirements, or time zone and attachment issues move to five to eight weeks because of sequential time entry retrieval, milestone card creation, and attachment re-upload with retry logic.

Adjacent paths

Related migrations to explore

Ready when you are

Move from TeamWork Live.
Land in Trello, intact.

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