Benchmark's New GP, and a16z & Sequoia's big Bet on Voice AI Wearables
Customer.io ARR Hit $100M
Customer.io ARR Hits $100M
Customer.io, a customer engagement and messaging automation platform founded in 2012, has officially exceeded $100M in ARR—a milestone confirmed in the company’s recent CEO announcement.
The company powers over 8,000 customers globally, delivering more than 64 billion messages in the past 12 months across email, push, SMS, in-app messaging and webhooks.
The platform addresses the challenge of fragmented customer data and legacy tools by enabling technical marketers and product teams to build behavior-based campaigns and cross-channel messaging flows with ease.
By unifying first-party data, enabling real-time segmentation and facilitating multi-channel automations, Customer.io helps companies convert trial users into advocates, retain at-risk customers and grow engagement without turning every change into an engineering project.
From a financial and operational perspective, Customer.io has grown capital-efficiently: the company was projected to hit around $78 M ARR at the end of 2024, at ~35% year-over-year growth.
With the $100M ARR threshold now crossed, the company indicates it will expand its infrastructure and partnership ecosystem, invest further in AI-driven personalization and maintain its distributed workforce while scaling reliably.
Benchmark’s New GP: Everett Randle
In late July, Victor Lazarte — who led Benchmark’s investment in HeyGen — announced he was leaving the firm to start his own VC fund. Combined with the earlier departures of Miles Grimshaw and Sarah Tavel (who recently transitioned to Venture Partner), Benchmark has now lost three GPs in just two years.
Two days ago, Benchmark announced a new General Partner: Everett Randle, previously a partner at Kleiner Perkins (KP). I first came across him through his 2021 essay “Playing Different Games,” a sharp breakdown of Tiger Global’s blitzscaling investment playbook.
After joining KP, Everett led the firm’s Series B investment in the AI video startup Captons(now Mirage), a company that took AI video generation to its limits.
He later spearheaded investments in Glean, Chainguard, and Huntress — some of KP’s strongest AI-related bets over the past two years. Before that, during his time at Founders Fund, he backed Rippling, Wave, and Stord.
Benchmark shared this statement on X:
Benchmark was founded in 1995 by a group of entrepreneurs and investors in their 30s. Over the last 30 years, it has been continuously reshaped by people of similar spirit.
We’ve always believed in one simple truth: great teams are built by those who put collective success above personal fame.
We look for partners who resist the industry’s trend of distancing themselves from founders — people who engage directly, who see this work not as a career, but as a lifelong mission.”
Benchmark added that Everett’s track record shows “exceptional judgment,” coupled with “relentless curiosity, sincere humility, and a quiet competitiveness that lifts everyone around him.”
The firm reaffirmed its flat structure — all equal partners with equal power, responsibility, and ownership — saying that when someone embodies Benchmark’s founding DNA, “the mutual recognition happens instantly.”
Benchmark’s AI Bets Keep Paying Off
Over the past two years, Benchmark’s AI portfolio has been nothing short of remarkable. Most of its lead investments either saw rapid revenue growth or raised subsequent rounds within months — often both. And its coverage now spans nearly every major AI vertical.
Beyond early bets like Mercor($500M Revenue Run Rate) and Sierra ($100M ARR), here are a few standout deals from the past year:
Reducto – an AI tool that turns unstructured data into structured knowledge. Benchmark led its $25M Series A in April, and just six months later, a16z led the $75M Series B.
Cursor – Benchmark participated in its $105M Series B; one of the hottest companies in the AI coding space.
Greptile – an emerging leader in AI-powered bug detection, where Benchmark led the $25M Series A.
Numeral – the AI-driven tax compliance automation startup. Benchmark led its $18M Series A in March, followed by a $35M Series B in September. The company now serves over 2,000 enterprise customers.
Exa – raised $85M in a round led by Benchmark. Exa is building “search for AIs, not humans,” positioning itself as the Google of the AI era.
Decart – an AI infrastructure company led by Victor Lazarte before his departure. It recently closed a $100M Series B at a $3.1B valuation, up 6× in just half a year.
LangChain – Benchmark led its $10M seed round two years ago. Less than a week later, Sequoia came in at a $200M valuation. Now, LangChain announced a $125M Series B at a $1.25B valuation.
Cerebras – one of Benchmark’s earlier AI hardware bets, just raised $1.1B in a Series G at an $8.1B valuation.
Legora - a collaborative AI platform for lawyers, which Benchmark led its $10.5m seed round, attracted a Series B funding of $80 million to a $675 million valuation. Now, sources say it is raising $100M at a $1.7 billion valuation.
Benchmark also remains one of the most active U.S. VCs in backing Chinese-founded AI projects:
It led HeyGen ($100M ARR), Manus ($90M annualized revenue), and Fireworks ($100M ARR).
a16z & Sequoia’s Big Bet on Voice AI Wearables
Meanwhile, one of the most intriguing recent AI deals — jointly backed by Sequoia and a16z — points toward the next major interface shift.