Project Management migration

Migrate from Project KickStart to Trello

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

Project KickStart logo

Project KickStart

Source

Trello

Destination

Trello logo

Compatibility

85%

11 of 13

objects map 1:1 between Project KickStart and Trello.

Complexity

BStandard

Timeline

1-3 weeks

Rollback included Accuracy guarantee Field-level validation

Overview

What this migration involves

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.

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

Project KickStart logo

Project KickStart

What's pushing teams away

  • Project KickStart is Windows-only with no documented public API, and customers report feeling locked in once their project history grows, making migration a manual and time-intensive process.
  • As teams grow beyond planning into collaborative execution, resource management, and real-time status updates, Project KickStart's static Gantt-centric model no longer meets their needs.
  • The product has not published a public roadmap or active changelog, leaving long-term customers uncertain about continued development and future compatibility with modern operating systems.

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 Project KickStart objects map to Trello

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

maps to

Trello

Board

1:1
Fully supported

Project 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

maps to

Trello

List

1:1
Fully supported

Phases 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

maps to

Trello

Card

1:1
Fully supported

Tasks 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

maps to

Trello

Checklist Item or Nested Card

1:many
Fully supported

Project 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

maps to

Trello

Custom Field or Card Label

1:1
Fully supported

Goals 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

maps to

Trello

Card Description or Card Comment

1:1
Mapping required

Notes 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

maps to

Trello

Card Member

1:1
Fully supported

Project 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

maps to

Trello

Card Label or Checklist Item

1:1
Fully supported

Obstacles 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

maps to

Trello

Card Dependency or Checklist Sequence

lossy
Fully supported

Project 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

maps to

Trello

Card Attachment

1:1
Fully supported

Attachments 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

maps to

Trello

Card Comment

1:1
Fully supported

Project 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

maps to

Trello

Board Template (manual rebuild documented)

1:1
Fully supported

Project 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

maps to

Trello

Not Migrated

1:1
Not supported

Project 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.

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.

Project KickStart logo

Project KickStart gotchas

High

No public API requires manual export-based migration

Medium

Windows-only desktop client limits access patterns

Medium

Goal, Obstacle, and Risk data requires custom mapping

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

  • No public API requires manual export-based migration

    Project KickStart has no documented public REST or bulk API. All migration work proceeds via CSV or XML exports from the Windows desktop client. We cannot initiate programmatic reads of live data. Customers must provide export files, and we validate the export against their source data before proceeding. This adds a manual step to scoping that most cloud-to-cloud platform migrations do not require. Projects with corrupted export files, non-standard encodings, or partial outline exports require manual correction before migration can proceed.

  • Export file quality determines migration fidelity

    CSV and XML exports from the desktop client can produce encoding inconsistencies, truncated outlines, and date format mismatches that silently alter data during import. We validate export files against the source data before any transformation begins, but any discrepancies discovered in the export file (rather than the source client data) may not be correctable through migration tooling alone. Customers on older Project KickStart versions should confirm export file integrity during scoping.

  • Task dependencies require a Power-Up decision

    Project KickStart generates explicit finish-to-start, start-to-start, and finish-to-finish task dependencies from the planning phase. Trello's native dependency graph is available only through the Card Dependencies Power-Up, which is a paid add-on. Free and Standard Trello plans require a workaround: we can convert dependencies to structured checklist sequences, but this does not produce a visible dependency graph in the Trello board interface. We confirm the Power-Up decision during scoping; if the customer intends to use Card Dependencies, it must be active before migration.

  • Trello board-level limits constrain large project imports

    Trello enforces board-level limits: approximately 500 cards per board, 1,000 checklist items per card, 50 labels per board, and member limits varying by plan. Projects with more than 500 total tasks or cards require splitting across multiple boards. We audit card and checklist counts during discovery and flag any project that exceeds these limits before migration. Customers on the Standard plan should verify that the custom fields add-on is active if Goals, Obstacles, or Risks are being mapped to custom fields.

  • Goals and Risks lack native Trello equivalents

    Project KickStart's Goals, Obstacles, and Risks are planning artifacts that have no structural equivalent in Trello. We do not discard this data; we map it to custom fields (Standard plan and above), card labels, or checklist structures. However, Trello does not natively track goal status, risk probability, or obstacle resolution over time. Customers relying on these planning objects should review whether the proposed label or checklist mapping in Trello provides sufficient tracking capability for their use case before migration begins.

Migration approach

Six steps for a successful Project KickStart to Trello data migration

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

  6. 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

Context on both ends of the pair

Project KickStart logo

Project KickStart

Source

Strengths

  • Wizard-led planning interface reduces planning anxiety for non-project-manager users
  • Gantt chart generation with explicit task dependencies from the outset
  • Project templates with drag-and-drop libraries for repeatable project structures
  • Act! and Outlook calendar integration for teams already in the Act! ecosystem
  • Targeted at regulated industries with structured, auditable project planning requirements

Weaknesses

  • No public API or documented export endpoint—data extraction relies entirely on the desktop client
  • Desktop-only application with no cloud or cross-platform access
  • Waterfall-only methodology does not serve teams using Agile, Scrum, or hybrid approaches
  • Limited collaboration features once the plan is created—no real-time status updates or team feeds
  • No visible product roadmap or public changelog, raising long-term viability concerns
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. 2 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 Project KickStart and Trello.

  • Object compatibility

    B

    2 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

    Project KickStart: Not applicable — no programmatic API surface published.

  • Data volume sensitivity

    B

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

Estimator

Estimate your Project KickStart 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 Project KickStart to Trello data migrations

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

Can't find your answer?

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Most Project KickStart to Trello migrations complete in one to three weeks. The export validation and scoping step typically takes three to five business days. The sandbox test migration adds another three to five days. Production migration and cutover run one to three days depending on data volume. Projects with more than 20 projects, extensive SubTask nesting, or complex dependency graphs move to three to five weeks because of the additional transformation and reconciliation work required to flatten the Project KickStart outline into Trello Cards.

Adjacent paths

Related migrations to explore

Ready when you are

Move from Project KickStart.
Land in Trello, intact.

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