Project Management migration
Field-level mapping, validation, and rollback between Project KickStart and Trello. We move data and schema; workflows are rebuilt natively in Trello.
Project KickStart
Source
Trello
Destination
Compatibility
11 of 13
objects map 1:1 between Project KickStart and Trello.
Complexity
BStandard
Timeline
1-3 weeks
Overview
Moving from Project KickStart to Trello is a methodology and access-model shift as much as a data migration. Project KickStart is a Windows desktop application built around Waterfall Gantt scheduling with a wizard-led planning interface and explicit task dependencies; it has no documented public API, so all data extraction relies on CSV and XML exports from the desktop client. Trello is a cloud-hosted Kanban platform organized around Boards, Lists, and Cards with a REST API, Power-Up ecosystem, and Butler automation. The migration maps your Project KickStart outline (Projects, Phases, Tasks, SubTasks) into Trello structure, converts dependency links to native Trello dependencies or checklist-based sequencing, and preserves Goals, Obstacles, and Risks as custom fields or card labels depending on your Trello plan. We do not migrate Power-Ups, Butler rules, or Project KickStart workflows; we deliver a written inventory of these for your admin to rebuild post-migration.
Every standard and custom field arrives verified.
AI proposes the map; you confirm before any record moves.
Parent–child, lookups, and ownership stay linked.
Calls, emails, meetings — with original timestamps.
Documents, uploads, and inline notes move with the record.
Why teams make this switch
Leaving
What's pushing teams away
Choosing
What's pulling them in
Object mapping
Each row shows how a Project KickStart 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.
Project KickStart
Project
Trello
Board
1:1Project KickStart Projects map to Trello Boards. Project name becomes the board title, description maps to the board description field, and cost maps to a custom field on the board. We preserve the source Project ID as a reference field for audit and reconciliation. If the customer uses multiple Project KickStart projects that share a theme, we create a Trello Workspace to contain the corresponding boards.
Project KickStart
Phase
Trello
List
1:1Phases are the second level of the Project KickStart outline and map directly to Trello Lists within the target board. Phase name becomes the List name, and the planned phase start and end dates are recorded as custom date fields on the first card in the list or as board-level custom fields depending on the Trello plan. We use the phase order from the outline to set List ordering.
Project KickStart
Task
Trello
Card
1:1Tasks are the primary work unit and map to Trello Cards. Task name becomes the card title, planned dates map to card due date and due date complete, owner maps to card members, cost maps to a custom number field, and completion percentage maps to card checklist progress or a custom number field. SubTask-level details from Project KickStart append to the card description with a structured prefix for disambiguation.
Project KickStart
SubTask
Trello
Checklist Item or Nested Card
1:manyProject KickStart SubTasks nest under Tasks. Where Trello Business Class or above is in use, we create nested Cards under the parent task Card. For Standard and Free plans, we flatten SubTasks into Checklist items on the parent Card, prefixing each name with the SubTask label for disambiguation. The customer selects the nesting strategy during scoping.
Project KickStart
Goal
Trello
Custom Field or Card Label
1:1Goals are a Project KickStart concept with no native Trello equivalent. We preserve them as a custom text field on each board card, or as a dedicated label with a structured prefix in the card title. Customers on the Standard or Premium Trello plan with custom fields enabled receive Goals as a custom long-text field; Free plan customers receive them as card description entries prefixed with GOAL: for manual extraction.
Project KickStart
Notes
Trello
Card Description or Card Comment
1:1Notes are free-text entries at Project, Phase, and Task levels. We append them to the target Card description field with a prefix indicating the source level. If the card description already contains structured content, we attach Notes as Card Comments to avoid overwriting existing data. The author and timestamp are preserved in the comment attribution.
Project KickStart
Assignee
Trello
Card Member
1:1Project KickStart assigns Tasks to named team members. We map Assignee names to Trello Workspace members by email match. Where the assignee has no corresponding Trello account, we flag the card for reassignment during the reconciliation step before production migration. Member mapping is validated in the sandbox migration before the production cutover.
Project KickStart
Obstacle and Risk
Trello
Card Label or Checklist Item
1:1Obstacles and Risks are Project KickStart-specific project risk entries with no direct Trello equivalent. We map them to a dedicated Card Label (RISK: or OBSTACLE:) on the related task card, or to a checklist titled Risk Register with each item containing the risk title and description. The customer's choice of label versus checklist is confirmed during scoping based on their risk-tracking workflow.
Project KickStart
Task Dependency
Trello
Card Dependency or Checklist Sequence
lossyProject KickStart generates explicit finish-to-start and start-to-start dependencies between tasks. We reconstruct these as native Trello Card Dependencies (available with the Card Dependencies Power-Up) where that Power-Up is active. For Free and Standard plans without the Power-Up, we convert dependencies to checklist-based sequencing on the predecessor card, ensuring that follow-on tasks are clearly ordered within the card structure. The customer chooses the dependency strategy during scoping.
Project KickStart
Attachment
Trello
Card Attachment
1:1Attachments linked to Project KickStart Tasks and Projects migrate as Card Attachments in Trello. We copy files to Trello by uploading directly to the card via the Trello API. File path references are not preserved since Trello stores attachments on its own servers. Customers with many large attachments should flag this during scoping to confirm that Trello storage limits are acceptable for their use case.
Project KickStart
Comment
Trello
Card Comment
1:1Project KickStart Comment Logs on Tasks migrate to Card Comments in Trello, preserving the comment text, author name, and timestamp. Comment ordering follows the original timestamp sequence. If a Comment references a SubTask or dependency context, we include a prefix in the comment body identifying the referenced element from the Project KickStart outline.
Project KickStart
Project Template
Trello
Board Template (manual rebuild documented)
1:1Project KickStart templates contain the outline structure, phases, and placeholder tasks. We export the template structure as a documented board layout in Trello and provide a written template rebuild guide specifying which Lists, standard cards, and custom fields to create in Trello to replicate the template. Trello Board Templates are rebuilt manually using the guide, as template export-import is not part of the automated migration scope.
Project KickStart
Act! and Outlook Integration Data
Trello
Not Migrated
1:1Project KickStart pushes tasks and calendar events to Act! CRM and Microsoft Outlook via proprietary integration. These external sync records do not live in Project KickStart's own data store and cannot be extracted from the export files. We do not migrate them. The customer's admin reconfigures Act! or Outlook sync integrations directly in Trello post-migration using the appropriate Trello Power-Up or native Atlassian Connect integration.
| Project KickStart | Trello | Compatibility | |
|---|---|---|---|
| Project | Board1:1 | Fully supported | |
| Phase | List1:1 | Fully supported | |
| Task | Card1:1 | Fully supported | |
| SubTask | Checklist Item or Nested Card1:many | Fully supported | |
| Goal | Custom Field or Card Label1:1 | Fully supported | |
| Notes | Card Description or Card Comment1:1 | Mapping required | |
| Assignee | Card Member1:1 | Fully supported | |
| Obstacle and Risk | Card Label or Checklist Item1:1 | Fully supported | |
| Task Dependency | Card Dependency or Checklist Sequencelossy | Fully supported | |
| Attachment | Card Attachment1:1 | Fully supported | |
| Comment | Card Comment1:1 | Fully supported | |
| Project Template | Board Template (manual rebuild documented)1:1 | Fully supported | |
| Act! and Outlook Integration Data | Not Migrated1:1 | Not supported |
Gotchas + challenges
Platform-specific issues from each side, plus the pair-specific challenges that don't show up on either platform's page on its own.
Project KickStart gotchas
No public API requires manual export-based migration
Windows-only desktop client limits access patterns
Goal, Obstacle, and Risk data requires custom mapping
Trello gotchas
Billing model uses maximum seat quantity at term midpoint
Custom Field data historically stored in pluginData
API rate limits are token-gated and can block bulk migration
Guest-to-paid seat conversion triggers on multi-board membership
Automation command runs are capped per plan and overage triggers upgrade pressure
Pair-specific challenges
Migration approach
Discovery and export file acquisition
We audit the customer's Project KickStart environment for project count, phase depth, task and SubTask volume, attachment count, custom field usage, and active integration exports. Because Project KickStart has no API, we guide the customer through generating CSV and XML exports from the Windows desktop client. We validate export file integrity against the source data and identify any records that cannot be represented in the export format. This step produces a written migration scope document confirming what data is migratable and what requires a workaround or manual post-migration rebuild.
Schema mapping design
We design the mapping from Project KickStart hierarchy to Trello structure: Projects to Boards, Phases to Lists, Tasks to Cards. We decide whether SubTasks become nested Cards or Checklist items based on the customer's Trello plan. We select the Goals, Obstacles, and Risks strategy (custom fields, labels, or checklist). We confirm whether the Card Dependencies Power-Up is active so we know whether to use native dependencies or checklist-based sequencing. All mapping decisions are documented in a schema map signed off by the customer before any data moves.
Sandbox test migration
We run a test migration into a Trello Workspace or board created specifically for validation. The customer's project lead reviews the board structure, card layout, dependency representation, and label usage. They spot-check 20-30 cards against the source Project KickStart data to confirm that task names, dates, assignees, and descriptions transferred correctly. We correct any mapping errors identified in the sandbox before the production migration. The sandbox step is required for all Project KickStart migrations because the export-file format introduces variability that is best validated against real data before cutover.
Owner and member reconciliation
We extract every distinct Assignee from the Project KickStart export and match them to Trello Workspace members by email address. Any Assignee without a corresponding Trello account enters a reconciliation queue. The customer's admin provisions any missing Trello accounts and confirms member access to the target Workspace before production migration begins. This step is required because Trello card members must be resolved at the time of card creation; cards cannot be created with a member lookup that fails at insert time.
Production migration in dependency order
We execute the production migration in phases: first the Workspace and Board setup, then List creation in phase order, then Card creation in outline order with dependency links established after both predecessor and successor cards exist. Attachments are uploaded via Trello's API after the parent card is confirmed. Comments are appended using the card ID resolved during card creation. We run row-count reconciliation after each phase comparing migrated record counts against the validated export file counts. Task dependencies are reconstructed using the Card Dependencies Power-Up or checklist sequencing as agreed in scoping.
Cutover and automation inventory delivery
We freeze Project KickStart writes, run a final delta migration capturing any records modified during the migration window, then deliver the migration results. We provide a written automation inventory documenting any Butler rules, board buttons, or Power-Up configurations in Trello that replicate the workflow logic from Project KickStart planning artifacts. We do not rebuild automations as part of the migration scope. We support a one-week hypercare window to address reconciliation issues raised by the project team in the first days of live use in Trello.
Platform deep dives
Project KickStart
Source
Strengths
Weaknesses
Trello
Destination
Strengths
Weaknesses
Complexity grading
Standard Project Management migration. 2 of 8 objects need a mapping; the rest are 1:1.
Overall complexity
Standard migration
Derived from compatibility, mapping clarity, API constraints, and data volume across Project KickStart and Trello.
Object compatibility
2 of 8 objects need a mapping; the rest are 1:1.
Field mapping clarity
Field mapping is derived from defaults — final spec confirmed during the sample migration.
Timeline complexity
8-object category — typical timelines run 2–7 days end-to-end.
API constraints
Project KickStart: Not applicable — no programmatic API surface published.
Data volume sensitivity
Project KickStart doesn't expose a bulk API — REST + parallelization used for high-volume runs.
Estimator
Rule-based pricing — no per-record fees, no manual quotes. Migrations over 2M records are scoped individually.
Step 1
Pick a category, then your source and destination platforms.
Category
FAQ
Answers to the questions buyers ask most during Project KickStart to Trello migration scoping. Not seeing yours? Book a call.
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