The org chart was designed in the 1800s for a world where change moved slowly and a person's responsibilities could be fixed in advance. AI now shifts how work gets done by the day, sometimes by the hour. A generalist operator gives your company the ability to shapeshift at that speed instead of being boxed in by static roles.
I built a company made up entirely of generalist operators, with no specialists on the team, because that adaptability has become the most valuable skill set in the room. Here is the argument for why the timing matters.
The Org Chart Was Built for a Slower World
The shape of your company didn't come from nowhere. It came from the railroads. The earliest organizational charts were drawn to manage the operations of a nineteenth-century rail network, where the problem was coordinating known work across long distances [1].
Britt Gage frames it this way:
"The org chart was designed in the 1800s by a railroad engineer and the purpose of that org design was to have clear people in roles with responsibilities so that there were clear inputs and outputs for the work."
That structure was the correct answer to its moment. Technology moved at what, from where we sit now, looks like a crawl. You could codify a role, fill it, and reasonably expect the job to look the same in five years. Put known people in known seats and the outcome was predictable.
| The 1855 assumption | What holds in 2026 |
|---|---|
| The work is stable enough to codify | The work changes as the tools change |
| Each seat has a fixed scope | Scope shifts mid-quarter, sometimes mid-week |
| Coordination is the hard problem | Adaptation is the hard problem |
| Headcount is how you add capability | Capability can be added, orchestrated, or automated |
Why "Generalist" Got a Bad Name
The word carries a negative connotation that gets in the way of the hiring conversation. It sounds like a master of nothing, somebody running between problems without going deep enough in any of them to change the outcome.
- The assumption: a generalist covers many areas shallowly and can't build real strategy.
- What I've watched for a decade: the people who flex across areas are the only ones who can pick up fuzzy work, because they're deep in adaptability itself.
- The practical read: someone who is multifunctional, operational at their core, and able to build the infrastructure that makes a function run.
- The part that gets undervalued: discernment. Knowing what to abandon, unlearning as fast as learning, staying curious while rolling up sleeves.
Founders already understand half of this, because most of them are generalists. You are sales, you are marketing, you are customer success. The gap opens when it's time to grow the team, because the instinct is to solve a specific problem with someone who does that specific thing. That instinct is sound. It also has a second answer.
Change Used to Move by the Year. Now It Moves by the Hour
Organizations have always dealt with change. What's different is the clock speed.
Britt Gage describes the shift this way:
"Now, with AI changes accelerating the way that we're working is changing, not by the year, not by the month, sometimes by the day, and often even times by the hour."
Employers now expect skill churn across a large share of the workforce within five years, and they name AI and data as the fastest-growing capability demands [2]. Adoption keeps climbing across business functions, which means the question of what gets handed to an agent and what stays with a person is being re-answered continuously [3].
Three things are moving at once:
- The tools. New capability ships weekly, and the right workflow last quarter is the wrong one now.
- The boundary. What can be safely outsourced to technology is still being discovered in real time.
- The culture. Teams now include people and technology acting as people too, so new ways of working must be designed deliberately.
What Gets Lost When Every Role Is a Fixed Box
Work in the cracks
In an organization built entirely of specialists, work falls outside everyone's stated responsibilities. It's the stuff that appears because the company is growing or pivoting, and it belongs to nobody. It doesn't go away. It gets picked up by whoever will raise a hand, which is usually the founder.
The generalist you already employ
Often that hand belongs to someone with a specialized title who happens to have generalist instincts. Their job description says one thing and their actual week says another. They absorb the overflow quietly until the overflow becomes the job. Companies have run this way for a long time, which is also why the chief of staff role exists: a proxy to the leader who handles the strategic and functional work nobody else can carry [4].
Most teams treat chief of staff as the only route to this kind of person. There are others.
Depth Looks Different in a Generalist Operator
What makes this person effective isn't volume of tasks. It's a specific set of capabilities:
| Capability | What it produces |
|---|---|
| Multifunctional range | Coverage across marketing, GTM, sales, business ops, customer success, product, AI workflows, community, and chief of staff support [5] |
| Operational core | Infrastructure that lets a function keep running after the person moves on |
| Technology orchestration | Agents built, trained, and supervised alongside the human judgment work |
| Discernment | Things that aren't working get abandoned early |
| Learning by doing | Capability acquired inside your context, not transferred from a deck |
Where Specialists Still Win
I'm not describing a company where everybody is a generalist. The useful move is to route work by how well-defined it is.
| Nature of the work | Who it belongs to |
|---|---|
| Clear scope, repeatable, measurable | A specialist, full time or hired in |
| Known function with a stable playbook | A specialist |
| New, fuzzy, cross-functional | A generalist operator |
| Dependent on tools that keep changing | A generalist operator |
| Falling between existing seats | A generalist operator |
Clear work goes to the people who know exactly how to do it. Everything ambiguous goes to someone whose skill is handling ambiguity.
how We Do: Build a Nimble Infrastructure Around a Generalist Operator
- Inventory the overflow. For two weeks, write down every piece of work you personally absorbed that sits outside anyone's role. That list is your real hiring brief.
- Sort by clarity, not by function. Split the list into work with a defined scope and work that's still forming. Resist sorting it into marketing, sales, and ops. That sort re-creates the 1800s chart.
- Hire specialists against the defined half. Where scope is stable, a specialist will outperform anyone.
- Embed an operator against the forming half. Someone who joins your team, works in your tools, learns your business, and covers the rest. At oAT the capacity flexes up, down, and sideways as the work moves, so the engagement reshapes without a new hiring cycle.
- Re-sort every quarter. Work that has become clear graduates to a defined role. New ambiguity arrives. The routing exercise is the operating habit, and skipping it is how boxes re-form.
When Seats Stop Defining Impact
The payoff is that you decouple the functional arrangement of people in seats from the impact those people make. You spend less on hiring and re-hiring, because the person adapts instead of being replaced. You stop paying the tax of work that belongs to nobody. You get the right team at the right time rather than the team you designed nine months ago.
Britt Gage puts it bluntly:
"That is not how the world of work works now. That is never how startups have been built. And with how we're accelerating through the pace of change, it's not where the world is going."
Founders come to me with specific asks: scale go-to-market, stand up a sales motion, get content moving. A generalist does that work and builds the operating infrastructure underneath it, trains and supervises the agents that handle the repeatable parts, and keeps the relational judgment work with a human. Then, as the need changes, the person changes with it.
FAQ
Why can't a team of specialists handle a fast-changing company?
Specialists excel where scope is defined and repeatable. In a company that is growing or pivoting, work appears that sits outside every stated role, and a team of specialists has no owner for it. That work gets absorbed by the founder or by whoever volunteers, which is a sign the structure needs flexible capacity alongside the fixed roles.
Did generalist operators exist before AI, or is this a new idea?
Generalist operators have existed for a long time without a codified title. Chief of staff is the version most teams recognize, acting as a proxy to the leader both strategically and operationally. What AI changed is the frequency of change, which makes the skill set valuable enough to design an organization around rather than something that simply happens by accident.
What does "work in the cracks" mean for a growing organization?
Work in the cracks is the work that falls outside everyone's documented responsibilities, usually created by growth, a pivot, or a new tool. It is real and consequential, and it has no owner on the org chart. Left unassigned, it defaults to the founder, which is why leaders end up carrying more than the structure can absorb.
How is AI specifically changing the need for this role?
AI shifts what can be automated, what needs human judgment, and what a given workflow should look like, often faster than a hiring cycle can respond. Someone has to orchestrate the technology, build and supervise agents, and keep the judgment and relational work with people. That orchestration sits across functions, which makes it generalist work by nature.
References
- Library of Congress. "New York and Erie Rail Road diagram representing a plan of organization," Daniel C. McCallum, 1855. https://www.loc.gov/item/98688346/
- World Economic Forum. "The Future of Jobs Report 2025." https://www.weforum.org/publications/the-future-of-jobs-report-2025/
- McKinsey & Company. "The State of AI." https://www.mckinsey.com/capabilities/quantumblack/our-insights/the-state-of-ai
- Ciampa, Dan. "The Case for a Chief of Staff." Harvard Business Review, May–June 2020. https://hbr.org/2020/05/the-case-for-a-chief-of-staff
- Of All Trades. weofalltrades.com