Comparing Decagon and Gladly Sidekick? Both are AI Agents & Chatbots 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 | Decagon | Gladly Sidekick |
|---|---|---|
| Pricing | Per resolution · Custom | Paid · ~$180/seat/mo |
| Founded | 2023 | 2014 |
| Categories | AI Agents & Chatbots Enterprise | AI Agents & Chatbots E-commerce Support Help Desk & Ticketing |
| Integrations | Zendesk Salesforce Intercom Shopify Stripe Kustomer | Shopify Salesforce Zendesk Twilio Amazon Connect Slack |
Decagon builds what it calls an AI concierge: autonomous agents that resolve customer issues across chat, email, voice, and SMS, all sharing one brain and one memory of your customer. Instead of trapping your logic in brittle decision trees, Decagon uses Agent Operating Procedures, plain-language playbooks that describe how you want issues handled. Its voice agents answer with sub-second latency, handle interruptions gracefully, and can dial out as well as pick up, which makes them feel far closer to a competent human than to a phone tree.
The company's rise has been ridiculous in the best possible way. Founded in 2023 by Jesse Zhang and Ashwin Sreenivas, alumni of Google, Palantir, Citadel, and Scale AI, Decagon went from a standing start to a multi-billion-dollar valuation in roughly two and a half years, with its worth reportedly tripling in a single seven-month stretch as investors piled in. The name itself is a quiet math joke, nodding to the ten-sided polygon.
What keeps the logos coming is deployment quality. Decagon leans into white-glove onboarding, exposes full conversation logs so teams can audit and improve every answer, and routes genuinely hard cases to humans cleanly rather than bluffing. Its customer roster reads like a tour of the modern internet: Notion, Duolingo, Rippling, Eventbrite, Substack, Chime, and Affirm among them, plus larger enterprises adopting its outbound and proactive agents.
Pricing is sales-led and usage-based, offered per conversation or per resolution with volume discounts, so it is squarely an enterprise purchase rather than a quick self-serve signup you try on a whim. For teams that want an AI agent that feels concierge-grade, keeps a persistent memory of each customer, and can be tuned in the plain language a support manager actually speaks day to day, Decagon has become one of the most talked-about names in the category.
Read the full Decagon listing → · See Decagon alternatives →
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 →
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