Conversational AI company Gupshup has been marked down again by Fidelity, the third or fourth such cut since the US-based asset manager began backing it in 2021. Fidelity has reduced the fair value of its Gupshup stake to $3.35 million from the original $16.2 million it invested in 2021, Entrackr reported, citing the fund's latest disclosures.

In Fidelity's revised calculations, Gupshup is likely worth $270 million to $300 million, down from $1.4 billion in 2021. Fidelity wrote down the value of its holding twice in 2024, pegging the company's implied valuation at $486 million, 65% below the 2021 peak. The asset manager entered Gupshup's cap-table during its Series F round of $240 million, Tracxn data shows. That round also drew investors like Tiger Global, Malabar Investments, White Oak and Harbor Spring Capital.

Gupshup's most recent funding round, in July 2025, was struck at the same $1.4-billion valuation as in 2021. The company raised $60 million in that deal from Evolution X and Globespan Capital. Founded by Beerud Sheth in 2004, Gupshup sells conversational messaging tools that help businesses interact with customers across channels through bots, messaging APIs and related software. The company has clients in ecommerce, financial services and healthcare, among other sectors, Revenue comes from mobile messaging services, text-based advertising and software development fees.

Globally, it competes with Sierra, Avaya, Kore, Vonage and Agora. Gupshup's India business slowed down in FY25. Revenue from operations fell 5.3% to Rs 1,943 crore from Rs 2,051 crore a year earlier, Entrackr reported. Net profit dropped to Rs 26 crore from Rs 54 crore over the same period.

Employee benefit expenses at Gupshup India rose 10% to Rs 312 crore. Gupshup has been eyeing an IPO for some time. It had earlier explored a US listing, then considered shifting its headquarters to India and floating shares locally instead. But Sheth told The Arc in 2025 that the board was still evaluating whether an India IPO made sense.