Helpdesk migration

Migrate from Gladly to Zendesk

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

Gladly logo

Gladly

Source

Zendesk

Destination

Zendesk logo

Compatibility

50%

5 of 10

objects map 1:1 between Gladly and Zendesk.

Complexity

BStandard

Timeline

2-4 weeks

Rollback included Accuracy guarantee Field-level validation

Overview

What this migration involves

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.

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

Gladly logo

Gladly

What's pushing teams away

  • The mandatory 10-seat minimum ($1,800/month floor) and annual contract requirement lock small teams into costs they cannot justify, especially during off-season.
  • Seasonal e-commerce brands cannot scale seats down mid-contract, making Gladly cost-prohibitive for businesses with heavy Q4 volume and leaner off-periods.
  • Competitors like Freshdesk and Zendesk offer broader app ecosystems, more third-party integrations, and more granular ticket management features that Gladly lacks.
  • Support for escalation management, issue splitting/merging, and custom ticket properties is weaker than ticket-native platforms, frustrating teams with complex support workflows.
  • Some customers report difficulty getting adequate data exports when leaving, requiring involvement of Gladly Professional Services to facilitate historical exports.

Choosing

Zendesk logo

Zendesk

What's pulling them in

  • Mature omnichannel routing across email, chat, phone, messaging, and social — one unified inbox for support teams regardless of size or complexity.
  • Deep automation with Triggers, Automations, and SLA Policies lets high-volume teams enforce consistent workflows without manual ticket handling.
  • Large ecosystem of third-party integrations and a public app marketplace reduce friction for teams already using Salesforce, Jira, or Slack.
  • Industry-leading brand recognition and trust signal — many enterprise buyers default to Zendesk as a known quantity in vendor procurement cycles.
  • Generous documentation library and community mean onboarding teams can self-configure without needing a services engagement to get started.

Object mapping

How Gladly objects map to Zendesk

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

maps to

Zendesk

End User (User)

1:1
Fully supported

Gladly 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

maps to

Zendesk

Ticket

1:many
Fully supported

Gladly 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

maps to

Zendesk

Comment

1:1
Fully supported

Gladly 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

maps to

Zendesk

Tag

1:1
Fully supported

Gladly 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

maps to

Zendesk

Agent (User)

1:1
Fully supported

Gladly 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

maps to

Zendesk

Trigger / Automation (documented)

lossy
Fully supported

Gladly 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

maps to

Zendesk

Zendesk Guide Article

1:1
Mapping required

Gladly 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

maps to

Zendesk

Custom Field or Custom Object

lossy
Fully supported

Gladly'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

maps to

Zendesk

Extension / Target (documented)

lossy
Fully supported

Gladly 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

maps to

Zendesk

Report (documented)

lossy
Fully supported

Gladly 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.

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.

Gladly logo

Gladly gotchas

High

Historical conversation import is a paid Gladly add-on

Medium

Customer IDs change on profile merges

Medium

One open Conversation per customer constraint

Low

Default API rate limit of 10 requests per second

Low

Workflows do not export as data records

Zendesk logo

Zendesk gotchas

High

Data export requires API scripting on non-Enterprise plans

Medium

Automations cap at 500 active rules and 1,000 tickets per hour

Medium

Help Center has no native export feature

High

Custom Objects and full data export are Enterprise-only

Pair-specific challenges

  • Single open Conversation constraint creates ticket multiplication

    Gladly enforces exactly one open Conversation per Customer Profile at any time. When a new issue arrives from a customer who already has an open Conversation, Gladly adds it to that existing Conversation rather than creating a new case. Zendesk supports unlimited simultaneous tickets per End User. During migration, we must split each Gladly Conversation into individual Zendesk Tickets by Topic, channel, or issue type, which will visibly increase the ticket count in Zendesk versus the conversation count in Gladly. Customers must be briefed on this before cutover so agent queue expectations are aligned.

  • Historical conversation export requires Gladly Professional Services

    Gladly does not include historical conversation data export in the standard subscription. Customers leaving Gladly must either purchase a historical import add-on or engage Gladly Professional Services to generate the export file. We add this as a scoping item in the discovery phase and advise customers to initiate the export request with Gladly support as early as possible, since Professional Services turnaround can take several weeks and will delay the migration start date if not addressed early.

  • Gladly Workflows do not export as data records

    Gladly encodes routing logic, spam filtering, required disclosures, and handoff rules as Workflows that live in the application configuration layer. There is no API endpoint to enumerate or export Workflow definitions in bulk. We audit every active Gladly Workflow during discovery, document the conditions, actions, and logic branches in a written Workflow Inventory, and deliver it to the customer's Zendesk admin for manual reimplementation as Zendesk Triggers and Automations post-migration. This is a manual rebuild effort that is not included in standard migration scope.

  • Zendesk Guide requires separate activation before article migration

    Zendesk Guide (the knowledge base product) is a separate paid product from Zendesk Support and must be activated manually in the destination account before any article migration can begin. Gladly Answers articles cannot be imported into Zendesk until Guide is enabled. If Guide is not activated during scoping, article migration is deferred to after the initial cutover, leaving agents without access to migrated self-service content during the transition window. We flag this at discovery and coordinate activation with the customer's Zendesk admin before the Help Center export step.

  • Zendesk custom field type mismatches silently generate tags

    Zendesk converts drop-down and multi-select custom field values into tags automatically, which persist even after the field is removed from a ticket form. Gladly has no equivalent auto-tagging behavior. During mapping, we audit every Gladly custom field and explicitly configure Zendesk field types to minimize unwanted tag proliferation: single-select to Zendesk dropdown (not tag-based), multi-select to Zendesk multi-select with tag-generation awareness, and checkbox to Zendesk boolean. We run a test import in a Zendesk Sandbox to verify tag count before production migration.

Migration approach

Six steps for a successful Gladly to Zendesk data migration

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

  6. 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

Context on both ends of the pair

Gladly logo

Gladly

Source

Strengths

  • Native multi-channel (voice, SMS, email, chat) without separate telephony integrations.
  • Conversation-per-customer model preserves full context across interactions.
  • Flat-rate pricing with unlimited agents favors high-volume support centers.
  • AI-powered reply drafting and call summaries reduce agent handling time.
  • Strong brand roster (retail/e-commerce) with documented ROI on CSAT improvements.

Weaknesses

  • Minimum 10-seat contract creates a high floor for smaller teams.
  • Annual billing only — no monthly or pay-as-you-go options.
  • Limited escalation, issue-splitting, and ticket-property customization versus ticket-native platforms.
  • Smaller app marketplace and integration ecosystem than Zendesk or Freshdesk.
  • Historical data export requires a paid Gladly Professional Services engagement.
Zendesk logo

Zendesk

Destination

Strengths

  • Well-documented REST API with broad endpoint coverage for Tickets, Users, Organizations, and Help Center.
  • Rich automation primitives: Triggers (event-driven), Automations (time-based), and Macros with variable substitution.
  • Multi-brand support enables large organizations to route and isolate support by product line or subsidiary.
  • Scalable from small teams on Team plan to global enterprises on Enterprise Plus with sandbox and disaster recovery options.
  • Large partner ecosystem and marketplace with hundreds of pre-built integrations reduces integration work at deployment.

Weaknesses

  • Per-agent pricing with aggressive feature gating makes lower tiers feel artificially limited.
  • No native full-KB export — Help Center content requires API scripting to extract.
  • AI features are add-on priced and behave inconsistently, not deeply embedded in core workflows.
  • Implementation timelines for complex multi-channel setups routinely exceed initial estimates by weeks or months.
  • Knowledge base and help center functionality are separate from core ticketing with their own permission model and versioning.

Complexity grading

How hard is this migration?

Standard Helpdesk migration. 1 of 7 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 Gladly and Zendesk.

  • Object compatibility

    B

    1 of 7 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

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

  • API constraints

    B

    Gladly: 10 requests per second across all HTTP methods, with documented 429 responses and retry guidance.

  • Data volume sensitivity

    B

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

Estimator

Estimate your Gladly to Zendesk 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 Gladly to Zendesk data migrations

Answers to the questions buyers ask most during Gladly to Zendesk migration scoping. Not seeing yours? Book a call.

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Standard migrations covering Customer Profiles, Agents, and conversation history under 50,000 tickets typically complete in two to four weeks. Migrations with large historical conversation volumes (over 100,000 Conversation Items), active Zendesk Guide article migration, or custom object schemas extend to eight to twelve weeks. Gladly's mandatory historical data export (handled via Gladly Professional Services) can add several weeks to the pre-migration timeline and is negotiated directly with Gladly outside of FlitStack AI scope.

Adjacent paths

Related migrations to explore

Ready when you are

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