/Companies

Thankful

Acquired

San Francisco, US · Founded 2014 · 29 known investors

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Acquired by Gladly July 2023 · terms undisclosed · source ↗

Gladly offers an AI-based customer experience (CX) platform intended to help companies improve customer service and grow customer lifetime value while reducing agent workload and costs.

Also known as Thankful AI · Thankful.ai

Founders & leadership

Thankful was founded in 2014 by Joseph Ansanelli and Dirk Kessler.

JAJoseph Ansanelli
Joseph AnsanelliFounderHe has spent his career as an entrepreneur building and investing in companies.
DKDirk Kessler
Dirk KesslerCo-FounderCo-Founder; Principal Engineer (per Greylock portfolio page) at Gladly
EWEliza Wiraatmadja
Eliza WiraatmadjaVP Services and DeliveryEliza Wiraatmadja is VP Services and Delivery at Gladly. She has experience building and scaling teams focused on technical implementations, customer support, and educational content in enterprise software.
CCCandice Carvalho
Candice CarvalhoVP Strategic FinanceCandice Carvalho previously worked as a management consultant at Bain, where she led client relationships and financial analysis, and held roles at Google and Eventbrite managing executive partnerships and financial strategy. She is VP of Finance at Gladly, a customer service platform combining AI and human support.
MMMel MacAlister
Mel MacAlisterVice President of Customer SuccessMel MacAlister is VP of Customer Success at Gladly. She brings experience in sales, client services, and partnerships, with a background in cross-functional operations and process development at startups.
CBCharlie Besecker
Charlie BeseckerCEOChief Executive Officer at Gladly
ADAndy D'Amato
Andy D'AmatoChief Revenue OfficerChief Revenue Officer of Thankful, an AI-based customer experience platform. D'Amato has experience scaling go-to-market functions, sales, and customer success teams in the AI sector.
TRTodd Rakow
Todd RakowChief Financial OfficerTodd Rakow is CFO at Gladly, an AI-powered customer experience platform. He previously co-founded and sold Kanjoya, an NLP platform for HR teams, and held roles in corporate strategy at UKG, PayPal, and Fidelity.
AFAli Fazal
Ali FazalChief Marketing OfficerHe has spent over a decade in marketing leadership roles at startups, building demand generation, content, community, product marketing, and brand teams.
MW
Michael WolfeFounder

Board

JCJerry Chen
Jerry ChenInvestor and Board DirectorPartner at Greylock Partners

Investors · 29

Notable Capitallisted by Notable CapitalSilicon Valley · $5M – $50M

How we know: Notable Capital's portfolio page · a partner's Signal profile · the VCSheet dataset · open dataset · 5k.vc investor directory · Not right? Tell us

Also in the syndicate · 7

AVPleadAXA Venture Partners (AVP)BonfireJetBlue Technology VenturesMiramarOmegaTen-One-Ten

Funding

SEC filings, press & company announcements

$12M disclosed across 1 of 4 rounds · 2021

Source: company announcements and press reports — follow each round's link for the claim.

Company profile

researched Aug 2026

Thankful was a customer service software company that built an AI layer on top of existing helpdesks to read, route and resolve customer inquiries across written channels including email, chat, social media, in-app messaging and text. Its platform was organized around three products: AI Agent, which worked inside a brand's helpdesk like a human agent to tag and resolve requests such as missing packages, returns, exchanges and order tracking; Agent Assist, which intelligently routed tickets and suggested replies and next steps for human agents; and Insight, an analytics product giving enterprise clients real-time statistics and a unified view of customer service metrics. Rather than functioning as a scripted chatbot, the system personalized interactions using signals such as a customer's tone, location, purchase history and prior service history.

The company positioned customer service as a revenue driver rather than a cost center, arguing that brands invest heavily in acquisition marketing but hand inquiries to service teams with no knowledge of the existing relationship. It marketed primarily to consumer and ecommerce brands, and management described plans to extend into finance, insurance and healthcare verticals. Thankful integrated with and partnered with helpdesk providers including Zendesk, Kustomer and Gladly.

In July 2023, Gladly acquired Thankful and used its generative AI and no-code automation technology as the foundation of Gladly Sidekick, a self-service AI platform that pairs with Gladly's agent-facing Hero product. Sidekick centers on a no-code authoring tool for building automated conversation threads covering common requests such as managing an order, processing a return or requesting an exchange, drawing conversational responses from the Gladly Answers knowledge base and priced per assisted conversation. Thankful's co-founders moved to Gladly, with CTO Evan Tann joining as a Software Engineer Fellow.

Founding story

Ted Mico and Evan Tann founded the company in 2018 in Venice, California, out of frustration as consumers with customer service experiences; neither began with a background on the business side of the industry. Mico cited market research describing customer service as a $350 billion market and consumers spending roughly 43 days of their lives dealing with support, framing the company's goal as returning that time to customers.

Business model

B2B SaaS sold to brands as an application layer on top of their existing helpdesk software.

Thankful charged customers based on the volume of tickets handled and which of its products were used. Under Gladly, the derived Sidekick product moved to consumption-based pricing tied to the number of assisted conversations, alongside seat-based pricing for the agent-facing Hero product.

Traction

By September 2021 Thankful reported 400% year-over-year growth, more than 50 brand customers, and more than 30 million customer service tickets processed and learned from. The company cited Agent Assist making human agents up to 40% more efficient and AI Agent resolving up to 50% of queries. Named customers included Crate & Barrel, FabFitFun, MeUndies and UntuckIt; shared customers with Gladly included Bombas, Breeze Airways, Crate & Barrel, JOANN and MaryRuth Organics.

Latest developments

Following the July 2023 acquisition, Thankful's capabilities were transferred into Gladly Sidekick and the company was described as part of Gladly. Gladly (gladly.ai) now markets an agentic commerce and AI customer experience platform combining conversational commerce, lifelong customer memory, voice AI and agent-facing tooling, citing customer outcomes such as +19% conversion, +$34 average order value, 41% carts saved and results at MaryRuth's, Rothy's, KÜHL, Condé Nast and Deckers Brands.

▸Full profile — market position, technology, go-to-market, geography, history

Market position

Thankful competed in the AI customer service segment against helpdesk vendors and AI startups such as Zendesk, Kustomer and Level AI, differentiating itself as an AI application layer that plugged into incumbent helpdesks rather than replacing them. Its acquirer, Gladly, was positioned in the contact center and helpdesk market, appearing on G2's Top 50 list for customer service products and holding "high performer" status in the G2 Enterprise Grid Report for Contact Center, Summer 2023.

Positioned as more than a chatbot: the AI worked inside a brand's existing helpdesk like a human agent, resolving rather than only triaging requests, and personalized responses using customer context including tone, location and purchase and service history. Its focus on the post-purchase environment and on structuring largely unstructured service data was cited by its lead investor as the basis for investing.

Technology

Artificial intelligence and, later, generative AI applied to customer service, combined with no-code automation authoring. The platform operated as an application layer above the helpdesk, handling large volumes of queries across written channels, and was trained on more than 30 million historical customer service tickets. Personalization drew on customer attributes such as tone, location, purchase history and service history.

Go-to-market

Direct enterprise sales supported by a trial-style evaluation in which Thankful's agents listened in on a prospect's helpdesk for a couple of weeks to assess the state of its customer service and demonstrate results before purchase. The company also went to market through helpdesk partnerships with Zendesk, Kustomer and Gladly, including joint webinars and demos with Gladly.

Consumer and ecommerce brands with high volumes of written customer service inquiries; by 2021 the customer list included more than 50 brands.

Geography

Headquartered in Venice, California; its acquirer Gladly is based in San Francisco.

History

Founded in 2018 and based in Venice, California, Thankful spent more than two years building its AI customer service software before going to market. It reported 400% year-over-year growth and had processed and learned from more than 30 million customer service tickets by late 2021. It partnered with Gladly in 2020 and raised a $12 million Series A led by Alpha Edison in September 2021, bringing total funding to $15 million including a previously unannounced $3 million. Gladly acquired the company in July 2023, and Thankful's technology became the basis for Gladly Sidekick.

Compiled by commissioned research from 25 cited public sources — announcements, filings, and press listed under research sources below.

Key figures

latest reported
Agent efficiency improvement from Agent AssistSep 2021up to 40% more efficient
AI resolution rateAug 202676%
ARR (estimated)Oct 2024$47.7M
Brand customersSep 2021over 50 brands
Cost savings delivered to customersAug 2026$510M
CSAT increaseAug 202665%
Cumulative customer conversations processedAug 2026300,000,000
Customer queries resolved by AI AgentSep 2021up to 50% of queries
Customer service tickets processed and learned fromSep 202130,000,000 tickets
Employee countAug 2026222
HeadcountAug 2026222
LinkedIn followersAug 202619,402
Total funding raisedSep 2024$153M
Year-over-year growthSep 2021400%

Company-reported or press-reported figures, each dated to when it was claimed — not independently audited.

Founder mafia

2 people who came through Thankful went on to found or lead other companies.

Related companies · 6

Companies working in the same space as Thankful.

Customers & partners

Named customers · 16

BombasBreeze AirwaysBSN SportsCondé NastCrate & BarrelJetBlueKUHLMaryRuth'sNordstromOllieProClip USARothy'sThe Black TuxTUMIUlta BeautyWeNatal

Relationships the company or its partners disclosed publicly — case studies, joint announcements, press.

Timeline · 18

launches, deals, and filings
May 2026
Agentic Commerce capabilities announced at Gladly Connect Live

Gladly announces AI capabilities spanning the full customer journey (pre- and post-purchase), including presence on AI shopping surfaces like ChatGPT, Perplexity, and Gemini.

source ↗

Jan 2026
Two Gold Stevie Awards

Gladly wins Gold Stevie Awards for Best Use of AI in Customer Service and Best AI-Driven Customer Experience in the 2026 Stevie Awards for Sales & Customer Service.

source ↗

Jan 2026
2026 Customer Expectations Report published

Gladly and Wakefield Research publish a study of 1,000 US consumers finding 88% get AI/hybrid resolution but only 22% say it made them prefer the company — highlighting a loyalty gap in AI-driven service.

source ↗

Aug 2025
Named 'Best Overall Customer Experience Solution Provider'

Gladly wins industry award for bringing marketing-grade personalization to customer service.

source ↗

Jun 2025
CCW Excellence Award: Disruptive Technology of the Year

Gladly named Disruptive Technology of the Year at the 2025 CCW Excellence Awards, beating finalists including Microsoft, Observe.AI, and Krisp.

source ↗

Mar 2025
Launch of Sidekick on Voice

Gladly launches AI-powered voice support ('Sidekick on Voice'), extending its unified-conversation AI to phone calls.

source ↗

Feb 2025
Named to Constellation ShortList

Gladly named to Constellation Research's ShortList for Digital Customer Service and Support, Q1 2025.

source ↗

Sep 2024
$40M round led by AXA Venture Partners; unified AI platform launch

Gladly announces a $40M funding round led by AVP and launches a reimagined, AI-powered unified Customer Service Platform positioning support as a revenue driver.

source ↗

Jul 2023
Gladly acquires Thankful

Gladly acquired Thankful, a provider of generative AI and no-code customer service automation, and used its technology as the basis of Gladly Sidekick, a consumer AI and automation platform launched the same day. The two companies had partnered since 2020 and shared customers including Bombas, Breeze Airways, Crate & Barrel, JOANN and MaryRuth Organics. Deal terms were not disclosed.

source ↗

Jul 2023
Thankful founders join Gladly

Co-founder and CTO Evan Tann joined Gladly as Software Engineer Fellow following the acquisition; CEO and co-founder Ted Mico commented on Gladly carrying forward Thankful's vision.

source ↗

Jul 2023
Gladly Sidekick launched using Thankful's AI and automation technology

Gladly introduced Gladly Sidekick, a no-code AI and automation platform for customer self-service built on Thankful's technology, priced on a consumption basis according to the number of assisted conversations, and designed to work alongside the seat-based Gladly Hero agent platform and the Gladly Answers knowledge base.

source ↗

Sep 2021
Thankful raises $12M Series A led by Alpha Edison

Thankful announced a $12 million Series A round led by Alpha Edison, with participation from Bonfire, Ten-One-Ten, Greycroft, Omega Venture Partners and Miramar. Together with a previously unannounced $3 million, the round brought total funding to $15 million. Proceeds were earmarked for engineering hires and product expansion, with plans to move into finance, insurance and healthcare verticals.

$12M source ↗

Jan 2020
Thankful and Gladly begin partnership

Thankful partnered with helpdesk vendor Gladly in 2020, jointly serving shared customers before the 2023 acquisition. Thankful also partnered with Zendesk and Kustomer on the helpdesk side.

source ↗

Jan 2019
~$50M funding round

Gladly raises roughly $50M (per GetLatka aggregation), bringing disclosed cumulative funding to approximately $113M.

source ↗

Jan 2017
JetBlue Technology Ventures invests; JetBlue adopts Gladly

JetBlue's venture arm backs Gladly, and JetBlue itself switches to Gladly's platform to modernize airline customer service — an early, widely covered proof point.

source ↗

Jan 2016
Series A led by Greylock

Greylock Partners becomes Gladly's first institutional investor, first-partnering in a Series A round; additional 2016 funding brings the year's total to roughly $27M per aggregator data.

source ↗

Jan 2014
Gladly founded

Joseph Ansanelli, Michael Wolfe, and Dirk Kessler found Gladly in San Francisco to build a customer-centric (not ticket-centric) customer service platform.

source ↗

—
CEO transition: Charlie Besecker becomes CEO

Charlie Besecker, previously President of Gladly (confirmed in that title through at least June 2025), is confirmed as CEO by a May 2026 press release; founder Joseph Ansanelli transitions to Co-Founder and Executive Chairman. Exact transition date not publicly announced/found.

source ↗

Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.

In the news

▸Research sources · 25

primary sources listed

25 public sources were cited for this profile; the first-party ones are listed here.

Frequently asked questions

What does Thankful do?
Thankful built AI-driven customer service automation for ecommerce brands and was acquired by Gladly in July 2023.
Who founded Thankful?
Thankful was founded by Joseph Ansanelli, Dirk Kessler in 2014.
Who are Thankful's investors?
Thankful's investors include DCVC (Data Collective), Glynn Capital Management, Greycroft, Greylock Partners, Invariantes Fund, JetBlue Ventures, New Enterprise Associates (NEA), NewView Capital and 14 more.
How much funding has Thankful raised?
Thankful has disclosed $12M raised across 1 of its 4 known rounds.
Where is Thankful headquartered?
Thankful is headquartered in San Francisco, US.