Gladly

Gladly was founded in 2014 in San Francisco by serial enterprise-software entrepreneur Joseph Ansanelli together with co-founders Michael Wolfe (VP Products) and Dirk Kessler (Principal Engineer). Ansanelli had previously co-founded Clarify Inc. (enterprise CRM software) and Vontu (data-loss-prevention software, acquired by Symantec), and had a prior relationship with Greylock Partners before starting Gladly; Greylock became the company's first institutional backer, 'first partnering' in Gladly's Series A round, with partner Jerry Chen as the deal's Greylock representative. The company's founding thesis was that customer service software had forced a false choice between high-touch personalization and low-cost, deflection-oriented efficiency. Rather than building another ticketing system, Gladly built a platform organized around the customer — not the case — unifying every channel (voice, chat, SMS, email, social) into one continuous, lifelong 'Conversation' per customer.

Early traction included a notable investment and customer relationship with JetBlue: JetBlue Technology Ventures backed Gladly and JetBlue itself became an early adopter of the platform for airline customer service (widely covered in 2017–2019 press, e.g., Skift, Business Insider, WSJ). Gladly's institutional fundraising continued with additional rounds in 2016 (~$12M and ~$15M, per aggregator data), 2017 (~$36M) and 2019 (~$50M), bringing disclosed funding to roughly $113M by 2019 according to GetLatka. Revenue scaled from an estimated $10.9M ARR in 2021 to $30.5M in 2023 and an estimated $47.7M in 2024.

In September 2024, Gladly announced a $40M funding round led by AXA Venture Partners (AVP), alongside the launch of a reimagined, AI-powered unified Customer Service Platform aimed at turning support into a revenue driver rather than a cost center — bringing total disclosed funding to roughly $153M. The company subsequently renamed its product line (the AI product 'Sidekick' became simply 'Gladly'; the agent workspace 'Gladly Hero' became 'Gladly Team') and pushed further into agentic AI, launching 'Sidekick on Voice' in March 2025 for AI-powered phone support, and in May 2026 announcing 'Agentic Commerce' capabilities extending its AI across the full pre- and post-purchase customer journey (including surfaces like ChatGPT, Perplexity, and Gemini).

Business model

B2B vertical SaaS: an AI-powered customer experience / customer service platform sold primarily to mid-market and enterprise retail, direct-to-consumer, and consumer brands, often replacing or supplementing legacy ticket-based helpdesk systems (e.g., Zendesk, Salesforce Service Cloud).

Subscription/seat- and usage-based SaaS pricing for agent seats and platform access, plus AI-resolution/consumption-based pricing for its AI agent ("Sidekick"/Gladly AI) capabilities.