The future of the Chief of Staff role: when machines become agents
Things are changing fast and it's not all good news
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🚨New podcast episode!
A while back, I sat down with my friend Natan, Co-Founder @ SingleSprout, to chat about startup recruiting and the hiring process. You can check out the episode below!
🎉 I’m Hogan Certified!
I’m happy to share that I’ve officially earned my certification in Hogan Assessments!
This means I can now use these assessments to bring deeper insights into leadership potential, team dynamics, and personality-driven performance to every placement and engagement. I’ll primarily be using it to get the skinny on what it’s like working with a founder (beyond what they tell me : )) and to do deeper dives into candidates’ strengths, growth edges, and motivators and values. I’m excited to put these assessments to work for our clients and approach Chief of Staff matchmaking with a data-driven edge.
🫢 We went kind of viral on X this week
Our hedge fund client is offering a CoS role for $120-240k, but you have to basically be attached at the hip — 16+hr workdays, 7 days/week, no vacation or weekends, based in Puerto Rico, travel at a moments’ notice, etc.
But in return you’ll get an all-expenses paid lifestyle (food, housing, travel) and learn a ton from one of the best.
Some comments we got on this:
"20+ daily meetings is nightmare fuel"
"Comp needs to be 5x"
"First step before accepting the job is killing all of your loved ones to prove you want it." 😭
X post here if you want to read more unhinged comments lol.
I’ve been thinking for a while about what AI is going to mean for the Chief of Staff role.
Using a full blown tool or “muh, GPT wrapper” for scheduling or customer service already feels like old news, because AI has already crept into strategic areas that were once the sole domain of human leadership.
AI is becoming more agentic, which means these systems can make decisions, act independently, solve complicated problems, and adapt to new situations.
Why you should care (generally)
AI is coming for all sorts of jobs faster than most people think. We're on the fast track to AGI by 2027. This means we could have machines doing jobs better than your average college grad, and by the end of the decade, they’ll outsmart pretty much everyone. No one’s role will be spared.
Prediction #1: AI is taking over admin first
In just a few short years, AI will go from “helpful assistant” to straight-up coworker replacement.
To illustrate:
A Chief of Staff at a Series C startup is tasked with coordinating a quarterly all-hands meeting:
They need to align schedules for a 15-person leadership team across 4 time zones.
Prepare a detailed agenda.
Send invites.
Handle last-minute conflicts, cancellations, and reschedules.
Here’s how it works with an AI agent:
The CoS CCs an AI agent on the planning email.
The agent instantly gathers availability, resolves scheduling conflicts, and locks in a time.
It auto-generates an agenda template based on past meetings.
All RSVPs and follow-ups are managed in real-time.
Why this matters:
Coordinating a meeting like this could take HOURS of back-and-forth emails and calendar juggling. Really high-cost Chief of Staff time is spent on low-value logistics. Now, AI agents can handle the entire process seamlessly — for pennies.
Hourly Cost Comparison:
Human Chief of Staff (~40hrs/week): $50/hour (assuming $100k/year salary).
AI Agent (24/7): $300/month ÷ (24 hours × 30 days) = $0.42/hour
42 of these bad boys = 1 hour of robot.
I’ts MUCH better to allocate the worker whose wage is 99% cheaper on low-value logistics tasks, and rotate your high-wage employee into higher value tasks. It’s a no brainer.
What this means is that admin-heavy Chief of Staff roles are officially on borrowed time — to remain relevant, they need to evolve beyond admin and logistics. Strategic thinking, stakeholder alignment, driving high-value initiatives — these are the more irreplaceable aspects of the role. If your time as a Chief of Staff is spent organizing meetings and handling inboxes, AI isn’t coming for your job because it kind of already has.
I think by 2026, many of these purely admin CoS roles are going to be phased out or radically diminished. There’s been this sort of bifurcation of the role happening over the years —> we have admin-like “Super EA” CoS vs. the more strategic advisor / thought partner / entrepreneur-lite CoS. We’re going to see a phasing out of the former, and a consolidation around the latter.
Prediction #2: AI will make the strategic CoS role more data-driven
As admin tasks disappear, AI will move up the ladder into more strategic work. For Chief of Staff roles, this means tools that analyze organizational data, create forecasts, and propose action plans — tasks that once required weeks of research and a team of analysts.
Imagine a CoS tasked with preparing the company’s annual strategy offsite:
The AI combs through financial reports, operational metrics, and market data.
It identifies bottlenecks, underperforming segments, and potential growth areas.
It drafts a slide deck with actionable recommendations for leadership.
What used to take a CoS weeks to assemble will be done in minutes, allowing them to focus on interpreting the data and driving the conversation with the executive team.
The shift that’s happening is the CoS role is less data gathering, more synthesis, and more insights that lead to better decisions (hopefully!). AI will elevate the strategic CoS by augmenting their ability to lead initiatives and focus on high-value projects, but it will also raise the bar for entry. The “strategic CoS” of the future will need to pair soft skills like stakeholder alignment with hard skills like data interpretation and tech fluency (example of this is I’m seeing more and more CoS job descriptions have fluency with GPT, Claude, and basics of workflow automation as table stakes).
Prediction #3: A new off-ramp for the Chief of Staff role is emerging
We’re going to call this Chief Automation Officer (CAO) — if not this, I’m fine with something like The Person Who Wrangles All The AI Agents for The Business, but I think that’s wordy : )
The CAO is responsible for overseeing the implementation, integration, and optimization of automation tools and technologies across an organization. To be effective, they need a full overview of the business — understanding workflows, pain points, and opportunities for improvement at every level.
This is a HUGE area of focus for founders and executives in every industry, at every stage, but who has the time? They’re already overwhelmed, and it takes a LOT of time and concerted effort to trial, successfully implement, and manage an AI agent and other tools.
Who better to handle this than a Chief of Staff? 😍
Chiefs of Staff already:
Operate as cross-functional problem-solvers, understanding how all parts of the business fit together.
Identify inefficiencies and propose solutions to improve team effectiveness.
Serve as a central hub for information flow between leadership and the broader organization.
The skills and perspective that make a Chief of Staff successful are the same ones that are critical for a CAO.
Why this transition makes sense:
The Chief of Staff is already a process architect. They understand how decisions are made, how teams collaborate, and where bottlenecks occur. This foundation is essential for automating workflows.
AI implementation needs a human touch. While technical teams may deploy automation tools, a CAO ensures that those tools align with organizational goals and culture. The Chief of Staff’s experience balancing strategy and operations makes them uniquely suited to bridge this gap.
CAOs shape the future of work. As organizations automate more processes, the CAO will play a pivotal role in deciding how humans and machines collaborate — a task that requires both technical understanding and a deep grasp of organizational dynamics.
This new career path offers a natural progression for Chiefs of Staff who want to take on a C-suite role without transitioning into traditional tracks like COO or CEO. The CAO role is emerging as a forward-looking, tech-enabled leadership position — and Chiefs of Staff are already positioned to fill it.
Prediction #4: AI will amplify leadership development
The Chief of Staff role has often been a stepping stone to C-suite positions. But as AI accelerates operational tasks, it will also provide tools for personal and professional growth, turning the CoS role into a “leader” incubator.
To illustrate:
An AI coach embedded in the CoS workflow could:
Provide real-time feedback on communication styles during meetings.
Analyze decision-making patterns and suggest areas for improvement.
Simulate scenarios (e.g., crisis management, negotiation) to develop leadership skills.
So the Chief of Staff not only supports the executive but also hones the skills required to step into those leadership shoes themselves, and make their leadership team more effective. (Maybe this even has an impact on the effectiveness and/or necessity of a team-wide executive coach?).
The implication is that the CoS of the future have always been executives-in-training, and they’ll leverage AI to learn faster than ever before. But again, the bar will rise — organizations will seek out CoS candidates with not only operational chops but also the potential to scale into a more strategic and visible leadership role.
Humans connections are the moat
If you’re already in a more strategic CoS role, you still have some breathing room, but I’m not sure how “comfortable” it’s going to be or for how long.
In Leopold Aschenbrenner’s Situational Awareness, he predicts that superintelligent AI will be automating some of the more analytical tasks soon enough. By the late 2020s, we’ll have AI systems capable of managing entire business units, understanding complex data flows, and even making high-level decisions. Imagine an AI agent that not only understands your OKRs but optimizes every piece of your strategy in real time, adjusting as it goes.
But as a businesses integrates agentic AIs to handle different aspects of their operations — whether that’s marketing, logistics, customer support, or internal communication — there will need to be someone who ensures these AIs work in harmony with each other and with human employees. These AIs won’t be perfect; they’ll need guidance, oversight, and continuous optimization. A strategic CoS, especially one with a technical background, is ideally suited for this role. Their job will be to manage not just the workflow of the organization, but the workflows of multiple agentic AIs, ensuring they align with the company’s objectives, adapt to real-time data, and communicate effectively with human departments.
So in the short term, before AI takes full control of complex strategic tasks, we’re going to see Chiefs of Staff evolve into hybrid roles — part integrator, part AI manager. Their focus won’t just be on people management or strategy anymore; it will also involve making sure these new, powerful AI systems work seamlessly together and enhance human productivity across the board.
AI can optimize, scale, and strategize until it’s blue in the face, but it can’t (yet) handle the human element: the complex interpersonal dynamics, the trust-building, the mentoring, and everything that makes a team actually work. If there’s a future for CoS roles, it's in maintaining the human connections that AI will continue to struggle with.
That’s where I think the strategic Chief of Staff holds a strong moat.
When it’s going down
By the end of this decade, we’re looking at superintelligent systems that are smarter than anyone on your leadership team. AI is already infiltrating CoS roles that lean heavily on administrative tasks, and the rest of the transformation will happen fast.
I predict that within the next few years, admin-heavy CoS positions will be some of the first to disappear, replaced by AI systems that don’t get tired, make fewer mistakes, and are ridiculously fast at learning new workflows. These shifts will start in tech-forward companies, and by the late 2020s, they’ll start hitting everywhere else.
But I do see the strategic CoS having a bit more staying power. I think the CoS will still be critical in any organization that values human input and collaboration. Leopold hints at this — AI will take over the technical and operational side, but people will still need to be at the helm, ensuring that AI aligns with human values and missions.
To recap
In short, we’re headed for a future where a lot of CoS roles as we know them won’t exist. The ones that survive and thrive will be the ones that embrace the human side of leadership. Empathy, communication, and a deep understanding of people will be the real differentiators.
Where things are going:
Admin CoS roles: Phased out by 2027, possibly sooner. AI is going to handle almost all of these tasks more efficiently and accurately than humans ever could.
Strategic CoS roles: These will stick around, but they’ll look different. Expect to be spending less time on the tactical side and more on guiding your team through complex, human-centered challenges that AI can’t touch. If you’re not focusing on emotional intelligence and team-building right now, you might want to start.
AI integration: AI won’t be a threat if you know how to use it. The most successful Chiefs of Staff will be the ones who learn how to work with AI, leveraging its strengths to amplify their strategic impact.
Human-centric leadership: Your ability to understand and manage people will be your strongest asset. This is the moat that will keep you valuable even as AI takes over other aspects of the role.
AI is going to need a human touch for quite a while yet. As agentic AIs become more embedded into the day-to-day workings of organizations, CoS roles will be central in ensuring that these systems function correctly within the complex human-machine hybrid environment. Someone with a deep understanding of both business operations and technology will need to oversee AI workflows, troubleshoot AI-driven processes, and ensure that the AI systems are aligned with the broader organizational goals.
A Chief of Staff who can manage a few agentic AIs, optimize their outputs, and align their operations with human-led departments will be invaluable. This person will likely become the integrator of tomorrow — a role that balances people, processes, and increasingly, machines.
The reality
We’re already in uncharted territory. The CoS role is evolving, and if you’re in it for the long haul, it’s time to think about what you bring to the table that an AI can’t replace.
AI will eventually outpace humans in nearly every technical domain, but I firmly believe that empathy, connection, and leadership will remain irreplaceable. In fact, I’m betting that these qualities will be at the heart of future roles — roles we can’t even fully envision yet. And as AI transforms the workplace, it will also create opportunities that don’t exist today, where uniquely human skills like emotional intelligence and authentic leadership will be more critical than ever.
And leaders of the future will seek out individuals with exceptionally high emotional intelligence, self-awareness, and authenticity (spoiler alert: they already are 😊).
Chief of Staff / Research Coordinator @ Investment Fund
This is truly a once-in-a-lifetime opportunity to learn directly from one of the industry's most brilliant minds.
Key Responsibilities:
Shadow and support the founder in all daily activities
Synthesize insights from 20+ daily meetings and distribute key information
Transform visionary ideas into actionable strategies
Drive research initiatives and special projects
Manage complex, shifting priorities with grace
Embrace whatever needs to be done - no task too big or small
The Reality (yes, really!) 👀
16+ hour days, 7 days a week
Constant international travel (primary base: Puerto Rico 🌴)
No fixed schedule - always on call
This IS your life for 2+ years
Must thrive under intense pressure
The ideal candidate has:
2-5 years of experience (finance background preferred but not required)
Exceptional academic performance
Track record of obsessive dedication to excellence
No ego about tackling any task
Burning desire to learn markets from a unique perspective
Something to prove 🔥
What They Offer:
💰 Base: $120-240k
🚀 Massive upside potential ($1M+ by year three)
🏠 All expenses covered (housing, travel, meals)
💸 Puerto Rico tax advantages
🤝 Access to elite investor network
📈 Path to becoming an investing legend
Important Note: This role is NOT for everyone. You must be willing to sacrifice everything else for this opportunity. No vacation time, no work-life balance - just pure dedication to excellence and growth.
If you're interested and want to learn more about the company, just apply here! We’ll get back to you ASAP if your experience aligns with what they’re looking for.
Check out our job board for the full list of opportunities with our clients!
Zomato’s Chief of Staff role is officially the “Most Viral CoS Role Ever”
Founders promoting 80hr work weeks are out here getting death threats
Pieter Levels’ Deadlift ETF is doing pretty good
Steve Jobs’ most important job was recruiting
Heart tissue can store memories
If you’re a candidate looking to get placed as a Chief of Staff with Right Hand, just submit this application.
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Where else you can find me: X and LinkedIn, where I post daily on all things Chief of Staff, personal growth, and consciousness.
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Until next time, Right Hand fam! 👋
This is SO HELPFUL. Thank you!
Well written and good food for thought about the future.