AI Summary
About
Gladly is an AI-first customer experience (CX) platform that organizes customer support around lifelong, person-centric conversations rather than discrete tickets. The company positions itself as “the only AI built for LTV,” explicitly contrasting its approach with deflection-first bots — its marketing argues that AI should engage and deepen customer relationships to grow lifetime value, not merely deflect contacts to cut cost. Gladly unifies voice, chat, SMS, email, and social into a single customer timeline so both human agents (which Gladly brands “Heroes”) and its AI (“Sidekick”) work from one continuous conversation history.
Gladly sells through a sales-led motion to midmarket and enterprise consumer brands. Publicly cited customers include Ralph Lauren, Tory Burch, Crate & Barrel, TUMI, ULTA Beauty, Rothy’s, PacSun, Nordstrom, Condé Nast, and Breeze Airways — a roster skewed toward retail, fashion, and consumer brands where customer lifetime value is a central business metric.
Founded in 2014 by Joseph Ansanelli (CEO, previously co-founder of Kana and Vontu), Michael Wolfe, and Dirk Kessler, Gladly was incubated at Greylock and has raised roughly $208M across six rounds from GGV Capital, New Enterprise Associates, Glynn Capital, Riverwood Capital, and others, with its most recent round (~$40M) closing in September 2024. The company is privately held and does not disclose ARR or valuation.
Importantly, Gladly used to publish its prices openly. From 2019 through September 2024, gladly.com carried a full public price table — first a per-user model (Customer-Facing $150/mo, Task $38/mo, Admin/Reporting free), then named Hero/Superhero packages with a per-assisted-conversation AI charge. When Gladly migrated to the gladly.ai domain it removed the public table entirely, and the new /pricing/ URL now redirects to the homepage. This page therefore documents both the recovered historical prices (from Wayback Machine snapshots) and the current sales-gated state, plus third-party indicative figures clearly marked as such.
Pricing summary : how Gladly’s sales-gated seat-plus-outcome model works
Gladly uses a two-part hybrid model combining a seat-based platform fee with outcome-based AI pricing. Until late 2024 these figures were published; today they are sales-gated. The two dimensions are:
- Per-Hero seat package (seat-based): Gladly licenses its agent-facing CX platform per “Hero” (its term for a human support agent). The last published rates were a Hero package from $180/hero/mo (10-hero minimum) and a Superhero package from $210/hero/mo (45-hero minimum), both billed annually with voice included.
- Sidekick AI per-assisted-conversation charge (outcome-based): Gladly’s AI, “Sidekick,” is priced on an outcome basis — $0.60 per assisted conversation (opt-in, with a minimum volume commitment), with a lower rate available via annual commitment. A separate “Hero AI” feature set is fully included in the seat price.
This combination of a per-seat package and a per-outcome AI meter makes Gladly a textbook hybrid pricing model: the platform fee scales with headcount while the AI line scales with automated resolution volume.
What makes this different: Gladly splits human and AI billing along different value metrics — seats for human agents and assisted conversations for the AI — and ties the AI charge to an outcome-based pricing model (an AI-assisted resolution) rather than tokens, a direction also seen at peers like Intercom Fin and Gorgias. What is unusual is that Gladly retreated from public pricing — having published rates for five years, it now hides them behind a sales gate on gladly.ai.
Pricing by product
The figures below are Gladly’s last published prices from gladly.com (Wayback snapshots, September 2023 to September 2024). Gladly’s current gladly.ai page is sales-gated, so treat these as historical/indicative anchors rather than a live quote.
Gladly platform (Hero packages — last published 2024)
| Tier | Price | Included | Key mechanics |
|---|---|---|---|
| Hero Package | From $180 /hero/mo | Omnichannel timeline (voice, chat, SMS, email, social), People Match®, knowledge base, reporting | 10-hero minimum; billed annually; voice included |
| Superhero Package | From $210 /hero/mo | Everything in Hero plus custom reporting, 99.9% uptime SLA, Premium Support, increased API capacity | 45-hero minimum; billed annually; marked “Popular” |
Gladly Sidekick (AI — outcome-priced)
| Tier | Price | Included | Key mechanics |
|---|---|---|---|
| Sidekick AI | $0.60 /assisted conversation | AI self-service that resolves conversations or hands off to a Hero; opt-in add-on | Usage-based; minimum volume commitment; lower rate via annual commitment |
| Hero AI | Included in seat price | Agent-productivity AI (suggestions, summarization) bundled into the per-hero fee | Not usage-based; fully included in the Hero/Superhero package |
Earlier per-user model (2019–2022, superseded)
| Tier | Price | Included | Key mechanics |
|---|---|---|---|
| Customer-Facing user | $150 /user/mo | Front-line agents on all channels (voice included) | 8→10 seat minimum; annual contract |
| Task user | $38 /user/mo | Internal task/collaboration users | Add-on; requires a Customer-Facing seat |
| Admin/Reporting user | $0 | View-only reporting and analytics users | Free; requires a Customer-Facing seat |
Sales motions across products: historically self-serve-priced (published rates) but always sales-closed; today fully sales-led / Contact Sales for the Hero platform and Sidekick AI, with no PLG or self-serve tier and no public figures (gladly.ai, accessed 2026-06-07).
Hidden costs : what a sales-gated seat-plus-resolution bill can hide
Using Gladly’s last published rates, a real-world bill can be reconstructed. The structure points to where costs concentrate: a brand pays a per-Hero seat fee for every human agent and a separate $0.60 charge each time Sidekick AI assists a conversation. Note that current contracts are sales-gated, so live figures will differ from these 2024-published anchors.
Midmarket consumer brand — 25 Heroes, 10,000 AI-assisted conversations/mo (Hero package, last-published rates)
| Line item | Monthly cost |
|---|---|
| Hero seats — 25 × $180/hero/mo | $4,500 |
| Sidekick AI — 10,000 assisted conversations × $0.60 | $6,000 |
| Total (before voice/telecom fees) | $10,500 |
The striking result: at moderate automation volume, the Sidekick AI line ($6,000) exceeds the entire human-seat line ($4,500). Telecom/voice usage is billed separately on top. This dual-axis dynamic — a usage-like outcome charge layered over seats — is exactly what we cover in our guide to usage-based pricing fundamentals, and it means automating more conversations raises the bill even as seat counts hold flat.
Larger brand — 50 Heroes, Superhero package, annual commit
| Line item | Monthly cost |
|---|---|
| Hero seats — 50 × $210/hero/mo (Superhero, 45-hero minimum) | $10,500 |
| Sidekick AI — 25,000 assisted conversations × ~$0.60 (pre-commit) | $15,000 |
| Total (illustrative; annual commit lowers the per-conversation rate) | $25,500 |
For finance teams, the lesson from usage-invoicing and billing cycles applies directly: the seat line is predictable, but the per-conversation AI line is volatile and seasonal — peak-season contact spikes flow straight into the bill.
Want to estimate your own Gladly bill? Use the Gladly pricing calculator to model per-Hero seats plus the $0.60 per-assisted-conversation Sidekick AI charge across your own headcount and automation volume.
Pricing evolution : a sales-gated history with no public anchor price
Cadence
| Quarter | Price changes | Product / SKU additions | Notes |
|---|---|---|---|
| 2021 Q2 | 0 | 0 | 8-seat minimum for customer-facing users added to the long-stable Free / $38 / $150 per-user model. |
| 2022 Q1 | 0 | 0 | Repackaged the same prices into named tiers: Support Hero $150, Task User $38, Free User $0. |
| 2022 Q4 | 1 | 0 | Seat minimum raised from 8 → 10 seats. |
| 2023 Q1 | 1 | 1 | Two-package split introduced: Hero $150 and new Super Hero $180 (custom reporting, 99.9% uptime, Premium Support). |
| 2023 Q3 | 2 | 1 | Major AI pivot: Hero $180 / Superhero $210, plus a new $0.60 per assisted conversation Sidekick AI charge; Hero AI included. |
| 2024 Q3 | 0 | 0 | Last published-price snapshot ($180 / $210 / $0.60); Sidekick clarified as opt-in usage with a minimum volume commitment. |
| 2025 Q1 | 0 | 1 | Sidekick on Voice launched (press, 2025-03); pricing table removed as the site migrated to gladly.ai. |
| 2026 Q2 | 1 | 0 | 2026-06-07: gladly.ai /pricing/ 308-redirects to the homepage — pricing now fully sales-gated, no public figures. |
Tracked range: 2019-12 – 2026-06 (gladly.com via Wayback, then gladly.ai). Quarters not listed were verified stable (Free / $38 / $150 per-user model held from 2019 through early 2022).
Notable changes
- 2019-12 → 2021 — Per-user model held steady: Admin/Reporting free, Task user $38/mo, Customer-Facing user $150/mo (Wayback, gladly.com/pricing).
- 2021-06 — Added an 8-seat minimum for customer-facing users plus an annual contract (Wayback, 2021-06-21).
- 2022-03 — Repackaged into named Support Hero ($150) / Task ($38) / Free ($0) tiers (Wayback, 2022-03-24).
- 2022-11 — Seat minimum raised from 8 to 10 (Wayback, 2022-11-29).
- 2023-03 — Introduced the Hero ($150) / Super Hero ($180) two-package split (Wayback, 2023-03-20).
- 2023-09 — Major AI pivot: Hero $180 + Superhero $210, plus a new $0.60-per-assisted-conversation Sidekick AI charge (Wayback, 2023-09-28).
- 2024-09 — Last public price snapshot; Sidekick clarified as opt-in usage with a minimum volume commitment (Wayback, 2024-09-16).
- 2025-03 — Gladly launched Sidekick on Voice, extending AI to phone (PR Newswire).
- 2026-06-07 — gladly.ai
/pricing/now 308-redirects to the homepage; all pricing sales-gated (first-party capture). Third-party Vendr data indicates a ~$24,150 annual median contract (range ~$14K–$79K).
The retreat from public pricing in detail
Gladly is a rare case of a vendor that withdrew transparency. For roughly five years (2019–2024) gladly.com carried a complete, dollar-denominated price table — first a simple per-user model, then named Hero/Superhero packages with an explicit $0.60 per-assisted-conversation AI rate. When the company rebranded around AI and migrated to the gladly.ai domain, the public table disappeared and the /pricing/ path was reduced to a 308 redirect to the homepage. The recovered figures above all come from Wayback Machine snapshots of the former domain; the only current-era numbers are third-party buyer reports (Vendr), explicitly marked as indicative rather than Gladly-published.
What’s unique : anti-deflection, LTV-anchored, seat-plus-resolution pricing
1. AI billed on outcomes, humans billed on seats. Gladly deliberately splits its two cost drivers along different value metrics — per-Hero seats ($180–$210/mo) for human agents and a $0.60 per-assisted-conversation outcome charge for Sidekick AI — rather than forcing both into a single seat or usage meter.
2. Two flavors of AI, priced oppositely. Gladly distinguishes “Hero AI” (agent-productivity tooling, fully included in the seat fee, not usage-based) from “Sidekick” (customer-facing self-service, priced per assisted conversation). The same product line bundles one AI and meters the other.
3. Anti-deflection positioning. Gladly frames its AI around growing lifetime value and “devotion” rather than deflecting contacts to cut cost, an explicit contrast with deflection-first CX bots.
4. A vendor that removed its public prices. Unlike most peers who add transparency over time, Gladly published rates for five years and then withdrew them when it migrated to gladly.ai — its /pricing/ URL now redirects to the homepage and discloses nothing.
Strengths & weaknesses
| Strengths | Weaknesses |
|---|---|
| Outcome-based AI pricing ($0.60/assisted conversation) aligns revenue with resolutions | Removed its public price table; current figures require a sales call |
| Unified lifelong customer timeline across all channels (voice included) | Two-axis billing (seats + per-conversation AI) is hard to forecast at peak season |
| Strong enterprise consumer-brand customer base (Ralph Lauren, ULTA, Nordstrom) | High seat minimums (10 Hero / 45 Superhero) exclude smaller teams |
| Clear value-metric story (LTV, devotion) for retail/consumer CX | At moderate volume the AI line can exceed the entire human-seat line |
| Bundles agent-productivity AI (Hero AI) into the seat price | Sales-led only; no self-serve or free tier; telecom/voice billed separately |
Billing UX : a sales-gated quote-and-contract motion
- Contact Sales form — the primary pricing surface; collects name, work email, company, title, phone, and country to schedule an introductory call where current pricing is quoted.
- Demo gate (“Get a demo” / “Try it yourself”) — an interactive self-guided demo and a request-a-demo form act as the top-of-funnel before any pricing conversation.
- Annual billing + seat minimums — historical contracts billed annually with a 10-hero (Hero) or 45-hero (Superhero) minimum, and Sidekick AI required a minimum volume commitment before its per-conversation rate applied.
- No public price table (current) — the gladly.ai
/pricing/URL 308-redirects to the homepage; there is no online plan comparison, no self-serve checkout, and no published per-seat or per-conversation rate as of 2026-06-07.
Strategic wins : how outcome pricing and LTV framing reinforce each other
1. Tying AI revenue to assisted conversations aligns incentives with buyers
By charging Sidekick AI $0.60 per assisted conversation rather than per seat, Gladly only grows AI revenue when the AI actually does work — an alignment that resonates with the broader shift toward outcome-based pricing for AI. It also reframes AI from a cost center to a measurable outcome.
2. LTV positioning differentiates in a crowded deflection market
Anchoring on lifetime value and “devotion” rather than deflection gives Gladly a distinct narrative among CX-AI vendors, especially for consumer brands where repeat purchase and loyalty drive the business. The framing also dovetails with the value-metric selection discipline central to durable usage-based pricing, and it sidesteps the value-metric problem that trips up many AI pricing teams.
3. Separating human and AI meters future-proofs the model
By metering Heroes (seats) and Sidekick (assisted conversations) independently, Gladly can let AI absorb more volume without forcing customers into a seat-count renegotiation. This decoupling is exactly the kind of structural flexibility we explore in our coverage of usage-based pricing for SaaS and AI, and it keeps the platform fee stable while the outcome line scales with automation.
Areas to improve : transparency gaps in a fully sales-gated model
1. Restore at least an anchor price or starting band
Gladly used to publish a starting per-Hero band and an explicit $0.60 per-conversation rate; removing them when it migrated to gladly.ai gives buyers no way to qualify the product before a sales call. Re-publishing a starting band — as most usage-based pricing vendors and many transparent SaaS pricing pages do — would reduce friction without giving away negotiated discounts.
2. Clarify how seats and assisted conversations interact on the bill
Because cost spans two axes, buyers need guidance on how seat counts and AI-conversation volume combine — our worked archetypes above show the AI line can exceed the seat line. A public calculator would help finance teams forecast a Gladly bill, much as the worked scenarios in our usage-based billing guide do for metered products.
3. Define “assisted conversation” publicly to build trust in the outcome meter
Outcome-based pricing only works when both sides agree on what counts as a billable unit. Publishing a clear, auditable definition of an “assisted conversation” — and how partial or escalated conversations are treated — would reduce the disputes that often accompany outcome-based AI pricing and make the $0.60 meter easier to trust.
Key takeaways
- Split your value metric when your product has two distinct cost drivers. Gladly charges seats ($180–$210/hero/mo) for humans and $0.60 per assisted conversation for AI, matching each meter to what the buyer actually values. The result is a bill that scales differently for headcount than for automation.
- Outcome-based AI pricing is becoming a category norm. Charging $0.60 per assisted conversation rather than per seat ties revenue to delivered work. It mirrors the direction seen across the CX-AI space at peers like Intercom Fin and Gorgias.
- Positioning shapes the value metric. Gladly’s anti-deflection, LTV-first story makes “conversations that deepen relationships” — not deflected tickets — the unit it bills on. The narrative and the meter reinforce each other.
- Withdrawing transparency has a cost. Gladly published prices for five years, then removed them when it rebranded around AI. Hiding rates behind Contact Sales removes self-qualification and makes comparison shopping impossible, which can lengthen sales cycles.
- Two-axis bills need forecasting tools. When cost spans seats plus a usage-like per-conversation meter — and the AI line can exceed the seat line — buyers need worked examples or calculators to budget confidently. Vendors that supply them lower buying friction.
UBP implications
- Outcome metrics can coexist with seats. Gladly shows that a $0.60 per-assisted-conversation AI charge can layer cleanly on top of a traditional per-hero seat fee. This gives vendors a hybrid path from seat-based to usage-based revenue.
- The assisted conversation is emerging as the canonical CX-AI value metric. Pricing AI per resolved/assisted conversation aligns vendor and buyer incentives. It is becoming the default outcome unit for support automation.
- Transparency is reversible, and the reversal is a signal. Gladly’s choice to remove published prices when it rebranded around AI trades buyer self-service for sales control. Vendors that pivot to outcome pricing often gate it precisely because per-unit rates invite comparison — a deliberate UBP packaging decision worth watching.
Sources
- Gladly pricing page (redirects to homepage) (accessed 2026-06-07)
- Gladly Contact Sales (accessed 2026-06-07)
- Gladly interactive demo (accessed 2026-06-07)
- Gladly pricing page — last published figures, archived (accessed 2026-06-07)
- Gladly pricing page — 2023 AI repackaging, archived (accessed 2026-06-07)
- Gladly pricing page — 2019 per-user model, archived (accessed 2026-06-07)
- Gladly blog (accessed 2026-06-07)
- Browse the full pricing blueprint corpus for peer customer-support pricing comparisons.
Bottom line
Gladly prices like its product is built: human agents (Heroes) on a per-seat package — last published at $180–$210/hero/mo — and AI (Sidekick) on a $0.60 per-assisted-conversation outcome charge. For five years those numbers were public; when Gladly rebranded around AI and moved to gladly.ai, the price table vanished and the page now redirects to the homepage. The model is legible, the history is recoverable, but the current dollars are gated — a rare example of a vendor walking transparency backward.
Want to compare Gladly against other customer-support pricing? Browse the pricing blueprint.
Pricing timeline : Major events on a vertical axis
Each milestone below corresponds to a public pricing change, product launch, or material adjustment. Major events use a filled marker; minor adjustments use a faded one.
Migrated to gladly.ai — pricing fully sales-gated
Gladly's public price table is gone. The gladly.ai /pricing/ URL 308-redirects to the homepage and all figures are quoted through Contact Sales. Third-party buyer data (Vendr) indicates a typical contract near a $24,150 annual median (range ~$14K–$79K). First-party capture 2026-06-07; figures above are Vendr-indicative, not Gladly-published.
Last published prices: $180 Hero / $210 Superhero, Sidekick opt-in $0.60
Final snapshot with public figures on gladly.com: Hero Package from $180/hero/mo (10-hero minimum, voice included) and Superhero Package from $210/hero/mo (45-hero minimum). Sidekick AI 'built in' at $0.60 per assisted conversation when opted in (minimum volume commitment); Hero AI fully included, not usage-based. (Wayback: web.archive.org/web/20240916022308)
AI pivot — Hero $180 + Superhero $210, plus $0.60/assisted conversation
Major repackaging combining 'heroes and AI working together.' Hero Package started at $180/hero/mo (10-hero minimum); Superhero Package (POPULAR) started at $210/hero/mo (45-hero minimum). Both added a $0.60 per assisted conversation charge for Gladly Sidekick AI, with Hero AI included. This is the first published per-resolution outcome rate. (Wayback: web.archive.org/web/20230928234738)
Hero $150 / Super Hero $180 two-package split
Gladly split into two packages: Hero at $150 per Support Hero/mo (10-seat minimum) and Super Hero at $180 per Support Hero/mo, adding custom reporting, 99.9% uptime, increased API capacity, and Premium Support. (Wayback: web.archive.org/web/20230320091255)
Seat minimum raised 8 → 10
Support Hero $150 / Task $38 / Free $0 held, but the customer-facing seat minimum rose from 8 to a 10-seat minimum with an annual contract. (Wayback: web.archive.org/web/20221129171427)
Repackaged into named tiers (Support Hero $150 / Task $38 / Free)
Gladly relabeled the model 'simple pricing' with named tiers: SUPPORT HERO $150/user/mo (8-seat minimum), TASK USER $38/user/mo, and FREE USER $0 (both add-ons require a Support Hero subscription). (Wayback: web.archive.org/web/20220324004014)
8-seat minimum added
Same Free / $38 / $150 per-user prices, but Gladly added a stated requirement: an 8-seat minimum for customer-facing users plus an annual contract. (Wayback: web.archive.org/web/20210621032127)
Per-user, consumption-based pricing (Free / $38 / $150)
On gladly.com, Gladly published a three-tier per-user model: Admin & Reporting users free, Task-Based users $38.00/mo, and Customer-Facing users $150.00/mo (Talk to Sales). All channels including voice were built in; consumption-based, annual contract. (Wayback: web.archive.org/web/20191212063033)
- · From 2019 to 2024 Gladly published prices openly on gladly.com — a Customer-Facing/Hero seat ran $150/mo, a Task User $38/mo, and an Admin/Reporting user was free.
- · When Gladly moved to gladly.ai it deleted its public price table entirely: the new /pricing/ URL now 308-redirects to the homepage, hiding every figure behind sales.
- · Gladly's 2023 AI repackaging introduced a $0.60-per-assisted-conversation outcome charge for its Sidekick AI — one of the earliest published per-resolution AI rates in CX software.
Questions & answers
- How much does Gladly cost?
- Gladly no longer publishes prices, but until late 2024 its public page listed a Hero package from $180 per hero per month and a Superhero package from $210 per hero per month (billed annually), plus $0.60 per assisted conversation for Sidekick AI. Third-party buyer data (Vendr) puts a typical contract near a $24,150 annual median.
- What did Gladly's pricing used to be?
- From 2019 to 2022, Gladly charged $150/month for a Customer-Facing (Hero) user, $38/month for a Task user, and $0 for Admin/Reporting users. In 2023 it repackaged into Hero ($180) and Superhero ($210) per-hero monthly packages with a $0.60 per-assisted-conversation AI charge.
- How does Gladly charge for its AI?
- Gladly markets its AI as Sidekick and prices it on an outcome basis at $0.60 per assisted conversation (when opted in, with a minimum volume commitment), layered on top of the per-Hero seat fee. A separate Hero AI feature set is fully included in the seat price, not usage-based.
- What is a Hero in Gladly pricing?
- Gladly calls human support agents Heroes and licenses the agent-facing platform per hero per month. The base Hero package historically required a 10-hero minimum and the Superhero package a 45-hero minimum, both billed annually.
- Does Gladly have a free tier?
- There is no self-serve free plan. Historically Gladly offered a free Admin/Reporting user seat bundled with a paid Hero subscription, but the platform is sold sales-led to midmarket and enterprise brands via a demo and Contact Sales form.