Comparing Gladly Sidekick and Zendesk AI Agents? Both are AI Agents & Chatbots and Help Desk & Ticketing tools in the directory, which is why buyers put them on the same shortlist. Below is a side-by-side look at how they price, what they integrate with, and when each is the better fit, so you can pick on the facts rather than either vendor's own sales page.
| Attribute | Gladly Sidekick | Zendesk AI Agents |
|---|---|---|
| Pricing | Paid · ~$180/seat/mo | Per resolution · ~$1.50/resolution |
| Founded | 2014 | 2007 |
| Categories | AI Agents & Chatbots E-commerce Support Help Desk & Ticketing | AI Agents & Chatbots Enterprise Help Desk & Ticketing |
| Integrations | Shopify Salesforce Zendesk Twilio Amazon Connect Slack | Slack Shopify Salesforce Jira Microsoft Teams WhatsApp |
Gladly organizes support around people instead of tickets, and that one decision changes everything about how it feels. Every customer gets a single lifelong conversation thread that follows them across voice, chat, SMS, email, and social, so they never have to repeat themselves and your agents always see the full story. Sidekick, its AI agent, lives inside that thread, resolving requests using real customer context and taking genuine actions like tracking an order, starting a return, or making a change, then handing off to a human with everything already in view.
A recent standout is Sidekick on Voice, which Gladly bills as the industry's only AI voice agent powered by that lifelong, multichannel history, so a phone conversation picks up right where a chat left off. The company has kept expanding the family with Sidekick Sales for product recommendations, Sidekick Email, and versions that extend the agent onto Zendesk and Salesforce, so teams on other platforms can borrow its brain.
Gladly was founded in 2014 by Joseph Ansanelli and his co-founders, and it has leaned cheerfully into its theme, naming its pricing tiers Hero and Superhero. It is very much an enterprise product, sold largely by quote with seat minimums, and its Sidekick AI is billed per conversation or resolution on top. That positioning fits its customer base of consumer brands that treat support as a loyalty channel, including Crate and Barrel, Ulta Beauty, and Breeze Airways.
The through-line here is emotional as much as it is technical: Gladly wants every interaction to feel like talking to a company that genuinely remembers you and your history. If you sell to consumers who expect a personal, continuous relationship rather than a cold, fresh ticket every single time they reach out, Gladly and its Sidekick agent are built from top to bottom around exactly that promise.
Read the full Gladly Sidekick listing → · See Gladly Sidekick alternatives →
Zendesk AI agents resolve customer requests autonomously across email, chat, messaging, and voice, and they have the advantage of sitting on one of the most widely used support platforms on earth. Because they are built into Zendesk's help desk, the agents draw on your knowledge base and years of past tickets to answer questions instantly, then hand off to a human with full context when a conversation needs one. Zendesk also threads AI through the agent workspace itself with a copilot that suggests replies, detects intent, and summarizes long tickets.
The lineup comes in two flavors. The Essential tier bundles friendly generative answers into the Suite, while the Advanced tier, built on Zendesk's acquisition of Ultimate, goes fully autonomous, working off-script and calling your APIs to actually get things done. In keeping with where the industry is heading, the Advanced agents are billed per resolution, so you pay for issues solved rather than seats filled.
There is a fun irony in Zendesk's origins. The company was founded in 2007 by three friends in a Copenhagen loft who wanted support software that felt human instead of clunky, and its deliberately approachable branding helped it grow into an industry giant, go public, and later get taken private in a deal worth roughly ten billion dollars. More recently it has been on an AI shopping spree, absorbing companies to bolt voice, quality assurance, and deeper automation onto the platform.
Real customers put it to work in colorful ways: cosmetics brand Lush named its Zendesk agent Marvin and uses it to resolve a large share of first contacts. For the enormous number of teams already running support on Zendesk, switching on its native AI agents is often the shortest path of least resistance to real automation, with no new vendor to onboard and no data to migrate.
Read the full Zendesk AI Agents listing → · See Zendesk AI Agents alternatives →
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