The woman who cold-emailed her way to Twitter's 34th desk - and hasn't stopped since.
There's a two-word email that changed the course of Silicon Valley history, and it started: "I want." In 2009, a 23-year-old investment associate at Venrock named Jessica Verrilli cold-emailed Evan Williams and Biz Stone after watching them pitch at her firm. The email didn't ask for coffee. It didn't hedge. It said: "I want to work for you. Here are all the things I can do." Two weeks later she was Twitter employee #34.
That move - direct, operator-minded, zero ambiguity - has been her signature ever since. She didn't get the handle @jess by accident. She didn't acquire Vine and Periscope by being passive. And she didn't build a $75 million venture fund by waiting for permission.
Today Jessica Verrilli is co-founder and managing director of Adverb Ventures, the early-stage firm she launched in 2023 alongside April Underwood out of San Francisco's Presidio. The name is a clue. An adverb modifies a verb - it's not what you do, but how you do it. That's the thesis: how you build matters as much as what you build. The firm's tagline is "Build an extraordinary company, in good company." Not a slogan - a filter. Most of the founders she backs would not disagree with her face to face.
Fund I closed at $75 million in July 2023. Fund II is targeting $125 million. The portfolio already includes companies that Adverb's neighbors at the Presidio - with its views of the Golden Gate Bridge - would have to walk uphill to see clearly: AI-powered news reader Particle, Kayvon Beykpour's codebase intelligence platform Macroscope (which raised $40 million), Microsoft-acquired workspace tool Cove, and Mozi - Ev Williams' new private social network. Yes, Ev Williams. The man she once cold-emailed.
"I want to work for you. Here are all the things I can do."Jessica Verrilli - the cold email that got her hired as Twitter's 34th employee, 2009
Her 8.5 years at Twitter were not spent in meetings. She led approximately 30 acquisitions - not just the headline names, but the whole messy, competitive, strategic portfolio of deals that shaped what Twitter became. Vine came in 2012, when short-form video looked speculative and TikTok didn't exist. Periscope arrived in early 2015 before its public launch, acquired in what was essentially a race against Google and Facebook to prevent a bidding war. She also launched Twitter's London office in 2011, back when Twitter was still figuring out what it was.
Then she did something that generated its own news cycle: she left for Google Ventures in May 2015. Returned to Twitter five months later when Jack Dorsey came back as CEO. Left again in December 2017. This was not indecision - it was information-gathering. By the time she rejoined GV in 2018 as a General Partner, she had spent a decade watching what breaks, what scales, and which founders actually deliver. That's the kind of education you can't buy.
At GV, she led the $22 million Series B for Digits and joined its board. She backed Instawork, Homebound, and The Wing. She also started investing more aggressively through #ANGELS, the collective she co-founded in 2015 with five other former Twitter executives who had their own IPO liquidity and a shared thesis: that women should be on more cap tables. Not as a charity exercise. As an alpha play. Their portfolio grew to 100+ companies including Coinbase, Gusto, Airtable, Carta, and Stripe. Not a bad argument.
On the Gap Table: In 2018, #ANGELS partnered with Carta to publish landmark research quantifying something people said in theory but had never measured in public: female founders own 39 cents in equity for every dollar held by male founders. Female employees own 47 cents. Women hold 9% of equity value in Silicon Valley despite comprising 33% of the workforce. The research ran in the WSJ, Bloomberg, and the NYT. Jessica Verrilli put the number in the room.
None of this happened in isolation. Her network is not a Rolodex - it's a former operating system. The Adverb portfolio reads like a Twitter alumni directory because Verrilli understands, better than most, what it looks like when a great operator leaves a great company and starts something new. She's backed Sara Beykpour (who built Twitter's first Android app), Kayvon Beykpour (former Twitter CEO for product), and Ev Williams (Twitter co-founder). She didn't take these deals because of loyalty. She took them because she watched these people operate under pressure for years and knows what they do when it's hard.
The Presidio office is not incidental. Adverb hosts Founder Friday Hikes in the surrounding trails - the same national park she serves on the board of (Golden Gate National Parks Conservancy). She also runs the Builder Breakfast Club, a recurring gathering for 30 engineers and founders. This is intentional community-building, not networking. The difference is that one has an agenda and the other has snacks.
She describes her best thinking as happening on long trail runs. Before her first day at GV in 2018, she ran a 50-mile ultramarathon in the Pacific Northwest with 12,000 feet of elevation gain. She called it "hitting the ground running." It was a Medium post headline. It was also just true.
She grew up in Seattle - a Pacific Northwest native, she says, though she's been in the Bay Area for nearly two decades. At Seattle Prep, she was a lacrosse All-American and team captain who led her school to the Washington State Championship in 2003. Her father played lacrosse at Penn. At Stanford, she played varsity and enrolled in the Mayfield Fellows Program, an elite entrepreneurship track that places students in startup internships. That's where she met the world she ended up reshaping.
What makes her different from a dozen other former Twitter executives now running venture funds? The @jess handle is one signal - she got it because she was early and she kept it because she's still active. But the real answer is the way she thinks about the word "company." In Latin it means "those who share bread." She takes that seriously. The best founders she's backed, she's quick to say, are the ones who went to bat for their teams even when it cost them personally. She's watched enough deals close and enough companies collapse to know that character shows up in the spreadsheet eventually.
"Make sure the people around you are a great fit. That will shape your day-to-day experience more than almost anything else."Jessica Verrilli
Fund II at $125 million would more than double Adverb's assets under management. The firm writes checks from $500K to $5M across pre-seed through Series A, focusing on AI, enterprise software, healthcare, and consumer technology. Based on the portfolio pattern, "AI" means AI that changes how operators work - not AI for its own sake. Adverb again.
She has 318,000 followers on X/Twitter under @jess - a handle so short it's almost a credential on its own. She posts about founders, about equity gaps, about the mechanics of great company-building, and occasionally about Alaska Airlines. She is not performing. She is not building a personal brand. She is running a firm, backing founders, hiking in the Presidio, and occasionally running 50 miles before breakfast.
Somewhere Biz Stone still remembers the email.
In early 2015, six former Twitter executives each had a version of the same thought: the IPO had given them liquidity, the network had given them deal flow, and the gender composition of most startup cap tables was embarrassing. They decided to do something about all three at once.
The six co-founders of #ANGELS: Jessica Verrilli, April Underwood (former Chief Product Officer at Slack), Chloe Sladden (former Twitter VP Media), Jana Messerschmidt (Lightspeed), Katie Jacobs Stanton (Moxxie Ventures), and Vijaya Gadde (former Twitter Chief Legal Officer). Different trajectories, shared conviction: women on cap tables is not charity. It's a bet on better outcomes.
The portfolio now spans 100+ companies including Airtable, Anchorage, Carta, Coinbase, Gusto, and Stripe. That's not a list of companies that needed help. That's a list of companies that good investors got into early.
The Gap Table initiative (2018) was a different kind of move. In partnership with Carta, #ANGELS published the data everyone in the room already sensed but no one had quantified with receipts: female founders hold 39 cents in equity for every dollar of male founder equity. Female employees hold 47 cents. Women hold just 9% of all equity value in Silicon Valley, despite comprising 33% of the workforce. The research ran in the Wall Street Journal, Bloomberg, the New York Times, and USA Today. It wasn't a think piece. It was a dataset with a name.
Fund I backed 30+ companies across AI, enterprise software, healthcare, and consumer tech. Checks range from $500K to $5M. The common thread is founders who build as well as they pitch - and ideally, people Verrilli has watched under pressure before.
30+ companies backed personally before Adverb. Several are now household names.
"Build an extraordinary company, in good company."Adverb Ventures thesis - the phrase that stuck
"The best founders go to bat for their teams - even literally sacrificing their own comp - and no surprise, they rise to become standout leaders within the new, larger org."On X/Twitter, 2025
"Being a woman in this industry inspires me to push forward, connect with other women and serve as a role model."Refinery29 interview