Helpdesk migration
Field-level mapping, validation, and rollback between Gladly and Zendesk. We move data and schema; workflows are rebuilt natively in Zendesk.
Gladly
Source
Zendesk
Destination
Compatibility
5 of 10
objects map 1:1 between Gladly and Zendesk.
Complexity
BStandard
Timeline
2-4 weeks
Overview
Gladly's conversation-centric model treats every customer interaction as a continuous thread tied to a single Customer Profile; Zendesk's ticket-centric model allows multiple simultaneous cases per user. This fundamental architectural difference means we must split each open Gladly Conversation into discrete Zendesk Tickets by issue type or channel before migration, preserving the full message history as Comments. We resolve merged Customer IDs (which Gladly redirects rather than updates) by exporting both old and current IDs and mapping all history to the surviving record. Gladly's flat-rate pricing ($180-$210/user/month with a 10- to 45-seat minimum on annual contracts) contrasts with Zendesk's flexible per-seat tiers starting at $19/user on Team, making the cost argument for migration compelling for teams below Gladly's seat floor or managing seasonal volume. Workflows, automations, and routing rules are Gladly configuration rather than data records and do not export via API; we document every active Workflow for manual reimplementation in Zendesk. Zendesk Guide (knowledge base) is a separate product requiring manual activation before article migration begins, which must be sequenced before the Help Center export step.
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 Gladly object lands in Zendesk, including any object-level transformations, lookup resolution, or schema-design dependencies.
Typical mapping — final map is confirmed during the sample migration step.
Gladly
Customer Profile
Zendesk
End User (User)
1:1Gladly Customer Profiles map to Zendesk End Users. Each Profile has a unique Customer ID, unique email, and unique mobile number. We export both current and pre-merge historical Customer IDs because Gladly 301-redirects absorbed Profile IDs to the surviving ID while the Work Sessions Report retains the old value. In Zendesk, we store the original Gladly Customer ID in a custom field gladly_customer_id__c on the User record for cross-referencing and reporting continuity.
Gladly
Conversation
Zendesk
Ticket
1:manyGladly enforces a single open Conversation per Customer Profile at any time. We split each Gladly Conversation into individual Zendesk Tickets by Topic assignment and channel metadata (voice, email, SMS, chat). The split increases apparent ticket count in Zendesk compared to Gladly's conversation count, which the customer's CX lead must acknowledge before cutover. Closed Conversations map to Zendesk Ticket status (Solved/Closed); open Conversations map to Open status.
Gladly
Conversation Item
Zendesk
Comment
1:1Gladly Conversation Items represent individual messages across all channels within a Conversation. We export all Items with timestamps, channel metadata (type, direction, agent attribution), and body content. In Zendesk, each Item becomes a Comment on the corresponding Ticket, with the original channel preserved in a custom field original_channel__c so agents know whether the interaction originated as email, chat, SMS, or voice.
Gladly
Topic
Zendesk
Tag
1:1Gladly Topics are taggable labels applied to Conversations for routing and analytics. We export Topic assignments and apply them as Zendesk Tags. Tags serve as the primary classification mechanism in Zendesk equivalent to Gladly's Topic model. Tag names are preserved exactly to maintain continuity in any reporting or routing rules that reference them.
Gladly
User / Agent
Zendesk
Agent (User)
1:1Gladly User records include name, email, role, and permission set. We export all active and inactive agents and map them to Zendesk User records, preserving role assignments (Agent, Admin) and group memberships. Agents without an email match in the Zendesk destination are held in a reconciliation queue for the customer's admin to provision before record import proceeds.
Gladly
Workflow
Zendesk
Trigger / Automation (documented)
lossyGladly Workflows encode routing logic, spam filtering, required disclosures, and agent handoff rules as configuration rather than data records. There is no bulk API endpoint to export Workflow definitions. We audit every active Gladly Workflow during discovery, document the trigger conditions and actions in a written specification, and deliver it to the customer's Zendesk admin for manual reimplementation as Zendesk Triggers and Automations post-migration.
Gladly
Knowledge Base / Gladly Answers
Zendesk
Zendesk Guide Article
1:1Gladly Answers articles, categories, and metadata export via API and map to Zendesk Guide Articles, Sections, and Categories. Zendesk Guide must be activated manually in the destination account before migration begins (it is a separate product). Article HTML bodies transfer directly; translated articles require a locale mapping step before import because Gladly and Zendesk handle multilingual article hierarchy differently.
Gladly
Custom Object
Zendesk
Custom Field or Custom Object
lossyGladly's custom object configuration requires extensive testing per G2 reviewers. We audit every custom object in the customer's Gladly account and design an equivalent Zendesk Custom Field (on Ticket or User) or Custom Object (Enterprise tier) schema before migration. Field types are mapped: Gladly text to Zendesk text, Gladly dropdown to Zendesk single-select, Gladly multi-select to Zendesk multi-select with the caveat that Zendesk generates tags from these fields automatically.
Gladly
Webhook
Zendesk
Extension / Target (documented)
lossyGladly exposes a webhook system with configurable events, retry policies, and ping events. We export webhook endpoint URLs, subscribed events, and retry configurations as a written inventory. The customer's admin re-establishes these as Zendesk Targets and Triggers in the Zendesk Admin UI post-migration, since Zendesk webhooks use a different configuration model (Extensions API rather than Gladly's webhook API).
Gladly
Report / CSV Export
Zendesk
Report (documented)
lossyGladly exports CSV and JSON reports via the UI and API. The Work Sessions Report retains old Customer IDs after profile merges, which we flag during scoping. We recommend exporting CSVs before migration and mapping them to Zendesk's Explore reporting workspace post-migration, noting that any existing Zendesk Guide report hierarchy will need to be rebuilt. Custom dashboards do not transfer.
| Gladly | Zendesk | Compatibility | |
|---|---|---|---|
| Customer Profile | End User (User)1:1 | Fully supported | |
| Conversation | Ticket1:many | Fully supported | |
| Conversation Item | Comment1:1 | Fully supported | |
| Topic | Tag1:1 | Fully supported | |
| User / Agent | Agent (User)1:1 | Fully supported | |
| Workflow | Trigger / Automation (documented)lossy | Fully supported | |
| Knowledge Base / Gladly Answers | Zendesk Guide Article1:1 | Mapping required | |
| Custom Object | Custom Field or Custom Objectlossy | Fully supported | |
| Webhook | Extension / Target (documented)lossy | Fully supported | |
| Report / CSV Export | Report (documented)lossy | Fully 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.
Gladly gotchas
Historical conversation import is a paid Gladly add-on
Customer IDs change on profile merges
One open Conversation per customer constraint
Default API rate limit of 10 requests per second
Workflows do not export as data records
Zendesk gotchas
Data export requires API scripting on non-Enterprise plans
Automations cap at 500 active rules and 1,000 tickets per hour
Help Center has no native export feature
Custom Objects and full data export are Enterprise-only
Pair-specific challenges
Migration approach
Discovery and data export negotiation with Gladly
We audit the Gladly account for Customer Profile volume, active Conversation count, Conversation Item volume by channel, Topic taxonomy, active User and Agent records, Workflow list, webhook configurations, and any custom object definitions. Simultaneously, we advise the customer to open a Gladly Professional Services ticket to request historical conversation export access, as this is a prerequisite that can take weeks to fulfill. We produce a written migration scope document covering record counts, object mapping decisions, and a timeline that accounts for the Gladly export delay.
Conversation-to-Ticket split design and Zendesk Guide activation
We design the conversation-split logic: each Gladly Conversation becomes one or more Zendesk Tickets, with the split rule (by Topic, by channel, by date range) defined during scoping based on the customer's issue taxonomy. We activate Zendesk Guide in the destination account and begin designing the Article, Section, and Category hierarchy to match Gladly Answers. Any custom object schemas are designed in Zendesk at this stage (Custom Fields on Ticket or User, or Custom Objects if the destination is Suite Enterprise), and the schema is deployed to a Zendesk Sandbox for validation.
Sandbox migration and record reconciliation
We run a full migration into the Zendesk Sandbox using production-like data volumes. The customer's CX lead and Zendesk admin reconcile record counts: End Users in, Tickets in, Comments in, Tags in, Article count, and Agent/User count. We spot-check 25-50 records against the Gladly source for field-level accuracy and verify that the conversation-split output produces the expected ticket structure. Schema corrections and mapping adjustments are made in Sandbox before any production data moves.
Customer ID resolution and owner reconciliation
We export both current and pre-merge Gladly Customer IDs for every Profile that has been merged during the account lifetime. Each historical ID is stored in a custom field gladly_legacy_customer_id__c on the Zendesk End User so that Work Sessions Report data from Gladly cross-references correctly in Zendesk. We extract every Gladly Agent referenced on Conversations and match by email against Zendesk Users. Agents without a Zendesk account go to a reconciliation queue for the admin to provision before production migration begins.
Production migration in dependency order
We run production migration in sequence: End Users first (with gladly_customer_id__c and gladly_legacy_customer_id__c populated), followed by Agents and Admins (User provisioning validated), then Tickets (with conversation-split applied and Comments attached in order), then Tags applied to Tickets, then Article migration to Zendesk Guide, then Webhook and Custom Object data. Each phase emits a row-count reconciliation report before the next begins. We throttle exports to Gladly's 10 requests per second API limit and use Zendesk's batch import endpoints with exponential backoff.
Cutover, delta sync, and Workflow handoff
We freeze new Gladly writes during cutover, run a final delta migration of any records created or modified during the migration window, then switch agents to Zendesk as the system of record. We deliver the Gladly Workflow Inventory document to the customer's Zendesk admin for Trigger and Automation rebuild. We provide a one-week hypercare window to resolve any record linkage issues (orphaned Comments, missing Tag assignments, incorrect User references). Zendesk Guide activation and article migration completeness are verified in this window. Post-migration admin rebuild and workflow training are outside standard scope.
Platform deep dives
Gladly
Source
Strengths
Weaknesses
Zendesk
Destination
Strengths
Weaknesses
Complexity grading
Standard Helpdesk migration. 1 of 7 objects need a mapping; the rest are 1:1.
Overall complexity
Standard migration
Derived from compatibility, mapping clarity, API constraints, and data volume across Gladly and Zendesk.
Object compatibility
1 of 7 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
7-object category — typical timelines run 2–7 days end-to-end.
API constraints
Gladly: 10 requests per second across all HTTP methods, with documented 429 responses and retry guidance.
Data volume sensitivity
Gladly 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
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Category
FAQ
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