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Gladly Sidekick vs Kustomer (2026)

Gladly and Kustomer both rethink support around the customer rather than the ticket, so they land on the same shortlists. Gladly centers a single lifelong conversation and prices per seat, while Kustomer builds on a unified CRM-style timeline billed per conversation. The choice is really seat-based relationships against conversation-based, data-rich workflows.

At a glance

Conversations/mo

% handled by AI

Agent seats

Price it at my volume

Estimates assume 5,000 conversations a month, 60% handled by AI and 10 agent seats, at each vendor's published list price (the cost calculator's model); treat them as a floor, not a quote. Compliance rows are what vendors publicly claim, and “Not verified” means we have not confirmed that fact yet, not that the tool lacks it.

Choose Gladly Sidekick or Kustomer?

About Gladly Sidekick

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 →

About Kustomer

Kustomer is a customer service CRM that throws out the ticket and rebuilds support around the person. Every conversation, order, and interaction lands on a single customer timeline, and its AI agents draw on that full history to answer personally, handling order status, changes, and refunds across email, chat, voice, SMS, WhatsApp, and social. It comes in two flavors that share the same no-code studio: an autonomous agent that resolves customer questions end to end, and a copilot that drafts and summarizes for human reps. Native AI Voice means the phone channel is built in rather than bolted on.

The company's history is a genuine plot twist. Kustomer was founded in 2015 in New York by Brad Birnbaum and Jeremy Suriel, the same duo who had earlier built Assistly, which Salesforce bought and turned into Desk.com. Meta then acquired Kustomer in a deal valued around a billion dollars, and about fifteen months later spun it back out to its original investors at roughly a quarter of that price, a rare corporate un-acquisition in which Meta even kept a minority stake. The deliberately misspelled name has stuck through all of it.

Now independent again, Kustomer raised fresh funding led by Norwest in 2025 and pushed its AI-native platform forward with automation and observability tools that trace exactly how an agent reached its answer. Pricing runs on annual seat tiers with an eight-seat minimum, plus a conversation-based option that unlocks unlimited users, and its autonomous agent is billed per engaged conversation.

Brands like UNTUCKit report meaningful productivity gains from putting the whole customer, not just the ticket, in front of every agent. If you believe support should feel like an ongoing relationship rather than a stream of disconnected, context-free cases, Kustomer's CRM-first approach is built from the ground up for exactly that.

Read the full Kustomer listing →  ·  See Kustomer alternatives →

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