The Deep View: Goodbye virtual assistant, hello AI Chief of staff

Posted on February 20, 2026 by michelleclarke2015
Goodbye virtual assistant, hello AI chief of staff
For over a decade, the tech industry has been racing to create the perfect virtual assistant. Now, the goal is rapidly shifting due to AI agents. The new north star is to create an AI chief of staff.
So, what’s the difference, and what does that look like? 
Siri, Alexa, Google Assistant, and countless other virtual assistants have been trying to cozy up to us for over a decade, automating tasks and reducing the number of steps to get things done. But they’ve mostly been pretty disappointing, limited to little more than announcing the weather, setting cooking timers, and helping dictate messages.
The new AI agent boom, led by Claude Code / Claude Cowork and OpenClaw, has changed the equation in just the past two months. Even just a few weeks ago, we were talking about how these new tools were finally launching the era of true “personal AI agents” that can perform routine tasks on our behalf. 
But the concept has advanced even further in recent weeks, especially driven by the OpenClaw community. The enthusiasts who are spinning up OpenClaw instances are racing ahead, giving us a picture of the future of agents. They have rapidly gone from trying to create super-smart, widely skilled agents to orchestrating teams of agents, each with dedicated strengths and specific capabilities, not unlike human teams. For many of these folks, they now have a stack of Mac minis running multiple agents and sub-agents.
And that’s where a different concept has now emerged: the AI chief of staff.
I first heard it from Jason Calacanis on This Week in Startups, where Calacanis was recently speaking to Mitesh Agrawal of Positron AI and said, “This is going to save you inbox management [and] Slack management. These are the chores that you typically, as CEO, would hire a chief of staff [or] an executive assistant to do. You’ve now used an OpenClaw agent to do [it].”
Agrawal reported that it’s saving him an average of at least 30 minutes per day. Calacanis pointed out that’s over 3 hours per week (for a startup founder) and 150 hours per year, which is the equivalent of getting 3 extra weeks per year. That kind of time savings compounds over time, and it’s likely to accelerate as the technology improves and gets easier for more people to access. 
Another concept Calacanis used to understand the power of this chief of staff phenomenon was to view it as democratizing services previously available only to the ultra-wealthy. He compared it to the way Uber can act like your personal chauffeur, Airbnb can function like having vacation homes in beautiful cities around the world, and JSX can make it feel like having a private jet. A chief of staff is someone who knows your needs and preferences and can act independently to make important tasks happen on your behalf. It was previously something limited to presidents, heads of state, and CEOs. That’s a lot for AI agents to live up to. But if they can pull it off, it will become one of the most powerful upgrades to everyday life that the current AI boom can deliver.
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About michelleclarke2015

Life event that changes all: Horse riding accident in Zimbabwe in 1993, a fractured skull et al including bipolar anxiety, chronic fatigue …. co-morbidities (Nietzche 'He who has the reason why can deal with any how' details my health history from 1993 to date). 17th 2017 August operation for breast cancer (no indications just an appointment came from BreastCheck through the Post). Trinity College Dublin Business Economics and Social Studies (but no degree) 1997-2003; UCD 1997/1998 night classes) essays, projects, writings. Trinity Horizon Programme 1997/98 (Centre for Women Studies Trinity College Dublin/St. Patrick's Foundation (Professor McKeon) EU Horizon funded: research study of 15 women (I was one of this group and it became the cornerstone of my journey to now 2017) over 9 mth period diagnosed with depression and their reintegration into society, with special emphasis on work, arts, further education; Notes from time at Trinity Horizon Project 1997/98; Articles written for Irishhealth.com 2003/2004; St Patricks Foundation monthly lecture notes for a specific period in time; Selection of Poetry including poems written by people I know; Quotations 1998-2017; other writings mainly with theme of social justice under the heading Citizen Journalism Ireland. Letters written to friends about life in Zimbabwe; Family history including Michael Comyn KC, my grandfather, my grandmother's family, the O'Donnellan ffrench Blake-Forsters; Moral wrong: An acrimonious divorce but the real injustice was the Catholic Church granting an annulment – you can read it and make your own judgment, I have mine. Topics I have written about include annual Brain Awareness week, Mashonaland Irish Associataion in Zimbabwe, Suicide (a life sentence to those left behind); Nostalgia: Tara Hill, Co. Meath.
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