Susan Hobbs runs global operations as Chief of Staff to the CEO at Automattic - the company whose software quietly runs more than two-fifths of all websites on earth. WordPress.com, WooCommerce, Tumblr, Jetpack, Day One, Pocket Casts. The open-source backbone of the modern internet. She is the person who makes sure 1,800 people working from everywhere are pointed in the same direction.
Before Automattic, she was the Chief of Staff to the CEO and COO at Cloudflare during one of its most consequential growth phases. Before that, she was a partner at CrunchFund - the seed fund co-founded by TechCrunch's Michael Arrington - where her portfolio included early bets on Airbnb, Vine, Cruise, Onfido, and X.ai. Before that, she spent four years as the architect behind TechCrunch Disrupt, the conference where companies like Dropbox and Airbnb famously launched to the world.
And before all of that, she was a public school teacher in Southern California. The instinct she carried out of that classroom - being present, reading the room, building connections across wildly different kinds of people - has followed her through every role since.
"Never leave very smart people with nothing to do because they will very quickly get bored - especially if they are entrepreneurial - and start something else." - Susan Hobbs
In 2004, Susan Hobbs drove north from Southern California, changed careers entirely, and walked into a hardware startup that almost nobody had heard of.
She joined Codian as the company's first non-engineering hire. What she could not have known yet was that Tandberg would buy Codian in 2007, and Cisco would buy Tandberg in 2008. She had picked a winner before anyone had to run the numbers.
She would do it again. CoTweet - a social media management platform - came next. She joined as the first non-engineering hire, again. ExactTarget acquired CoTweet in 2010. Salesforce acquired ExactTarget in 2013. Two startups. Two acquisitions. Two Fortune 500 outcomes. The pattern suggests either remarkable judgment or the kind of operational intuition that makes organizations want to be acquired.
The classroom, it turned out, was better preparation for this than it might look. Teaching requires you to read rooms fast, adapt in real time, motivate people who did not ask to be there, and keep a complex system moving under pressure. It is not so different from running startup operations - or producing a conference for 5,000 people across three cities on two continents.
"Teaching and venture capital share common requirements: being responsive and building strong interpersonal connections."
Susan joined TechCrunch as Director of Global Programming and spent approximately four years building the Disrupt conference into the kind of event where careers changed onstage. She ran Disrupt New York, Disrupt San Francisco, and Disrupt Europe in London. She ran the Crunchies Awards, where she recruited GZA of Wu-Tang Clan to perform. She commissioned agendas that put founders, investors, journalists, and the occasional celebrity into conversations that mattered.
Programming a conference is, at its core, an act of editorial judgment: who belongs in this room, what should they talk about, and what has to happen for the audience to leave with something they did not arrive with. Susan's version of that job produced stages where Startup Battlefield companies launched to the world and where the tech industry's fault lines - around money, power, diversity, and ambition - became visible in real time.
She left TechCrunch in May 2015 with a widely-read farewell post: Farewell TC, Hello YC. She was heading to Y Combinator as Director of Programming and Events. She lasted about fifteen months. Then she became a partner at CrunchFund.
CrunchFund was a seed-stage fund co-founded by TechCrunch's Michael Arrington. When Susan joined as partner in mid-2016, the portfolio already included some remarkable early bets. She worked alongside investments in Airbnb, Vine, Cruise (later acquired by GM), Onfido, and X.ai.
The CrunchFund years put her inside the earliest stages of companies that would become defining fixtures of the 2010s. Vine - the six-second video platform that Twitter eventually shut down in 2016 - was both a cultural phenomenon and a cautionary tale about platform dependency. Airbnb was, at early stages, a company that many serious people thought was a bad idea. Cruise became one of the most ambitious bets in autonomous vehicles. The portfolio had range.
Her observation about smart, entrepreneurial people becoming restless when left with nothing to do reflects the investment posture she developed during this time: back people with the drive to keep building even when no one is watching.
After CrunchFund, Susan moved into the Chief of Staff role she would hold at two of technology's most consequential companies. At Cloudflare, she was Chief of Staff to both the CEO and the COO during a period when the company was scaling rapidly - both in product surface area and in its public role as an arbiter of what gets to exist on the internet. The Chief of Staff role in a company like Cloudflare means sitting at the intersection of executive strategy, internal operations, and the kind of decisions that end up in news cycles.
She brought that experience to Automattic, where she now holds the equivalent role for a company with an even broader mandate: keeping WordPress, WooCommerce, Tumblr, Jetpack, Pocket Casts, Day One, Newspack, and the rest of the Automattic portfolio moving - across 1,800 employees distributed across the world, with no central office and the open source ecosystem as the underlying philosophy.
Automattic is a strange and specific kind of company. It is simultaneously a commercial software business and the steward of WordPress.org, the open-source project that now underlies more than 43% of all websites. Its distributed model predates the pandemic-era remote-work conversation by more than a decade. Running global operations there is not a standard Chief of Staff job. It is closer to running the logistics of a movement.
Since 2019, Susan has been an active angel investor, board member, and advisor. She also holds the title Chief of Momentum at The Human Board, a nonprofit organization. She invests in theatrical productions in New York and London - a choice that, on paper, looks like an odd detour from Silicon Valley convention. In practice, it reflects the same instinct that shaped her career: back people making things that require craft, audience, and the courage to perform in real time.
Theatre and startups share more than they appear to. Both require a group of people to believe in something that does not yet exist, to commit completely, and to ship it in front of a live audience with no option to roll back.
Working at Automattic means working inside an organization that has built its entire operational model around the assumption that the best people are not all in the same city. Susan's role as Global Operations Chief of Staff is, in this context, a genuinely global mandate. The 1,800-person team spans time zones, languages, and cultures. The coordination that a traditional HQ handles through proximity, Automattic handles through intention, tools, and people like Susan who understand how to build culture across distance.
Her Twitter handle is @slh - short, specific, not a billboard. Her blog is susanhobbs.blog - a domain that does not announce what it is before you arrive. She has built a career on operating at the center of consequential things without making the story about herself. In the attention economy, that is a kind of rare discipline.
She has been the first hire, the event producer, the VC partner, the Chief of Staff. The throughline is not the title. It's the instinct for knowing which rooms matter. - YesPress Editorial