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Rethinking company structures

Admin
April 8, 2026

AI is impacting development processes, it will also impact business and operational processes. What does that look like?

3 entries

Let's start by establishing the core goal of a company. Companies solve problems for people. Successful companies solve those problems efficiently. Very successful companies solve problems efficiently and show a true ROI to the people who have the problem. So if we're leveraging an AI system, the foundational prompt should define the problem the company solves, and any knowledge the company has should be viewed through the lens of how it relates to solving that problem.

We know that the merging of the Venn diagram of roles and responsibilities for developers will also happen on the business/operations side. So we should drill down into the existing roles to identify which tasks each role is responsible for. From there, we can start targeting tasks for removal and then consolidation.

The roles and responsibilities that come to mind are:

RolePrimary FocusTypical Tasks
Chief Executive Officer (CEO)Vision & StrategySetting company goals, forming strategic partnerships, deciding what products/services to build, final say on resource allocation.
Chief Operating Officer (COO)Efficiency & SystemsMonitoring workflows, optimizing internal processes, managing software subscriptions, ensuring other departments communicate.
Product ManagerWhat to buildAnalyzing user feedback, writing feature requirements, defining the product roadmap, prioritizing the engineering backlog.
Software EngineerHow to build itWriting code, deploying updates, managing databases, reviewing system architecture.
Quality Assurance (QA)Breaking thingsWriting automated tests, finding bugs before customers do, verifying that new features work exactly as the Product Manager requested.
Service Provider / SpecialistFulfilling the serviceExecuting the actual service (e.g., generating reports, writing copy, analyzing data) depending on what your company sells.
Customer Success ManagerClient retentionOnboarding new clients, running regular check-ins, proactively helping clients get more value from your product/service.
Tech Support / HelpdeskPutting out firesAnswering support tickets, resetting passwords, walking users through troubleshooting steps, escalating real bugs to engineering.
Marketing ManagerLead generationWriting blog posts, managing social media, running email newsletters, analyzing web traffic, creating ad campaigns.
Sales Development Rep (SDR)ProspectingSending cold outreach emails, qualifying inbound leads, setting up appointments.
Account Executive (AE)Closing dealsRunning product demos, negotiating pricing, drafting contracts, finalizing sales.
Bookkeeper / FinanceCash flowSending invoices, tracking expenses, reconciling bank statements, generating monthly profit and loss reports.
Administrative AssistantCalendar & InboxFiltering your personal email, scheduling meetings, organizing files, booking travel.

A key component of incorporating AI into your business is removing "knowledge sync" type activities. You probably shouldn't plop an AI into replace a role in your company without that AI being transparent about what it is doing, why it is doing it, and how it aligns with the problem the company is solving. That information should be stored in a company knowledge layer that other agents/humans interact with to stay aligned on core objectives. A shared knowledge store means that agents/humans can both extract the hyper-task-tuned context they need to complete their next task.

As mentioned in another post, every company will have some sort of Software Factory internally. It'll either be something they build themselves or buy. We can anticipate that as the cost of building software goes down, the willingness to "start over" on software will increase. For example, if I use my internal software factory to build a CRM tool and then realize that the CRM isn't solving the problem it was intended to solve, I can likely rebuild it from the ground up using lessons learned from the initial tool's failure. This would be unheard of today, but in the near future, I think it's the more likely way things will happen.

I'll start exploring the next steps in another post, but I think we've made good progress on laying the foundation with this initial post.

One note: the "one-person" company is slightly exaggerated. While it will certainly be possible to have a one-person company, at some point scaling to solve bigger problems will be necessary, and in those cases it will be good to have like-minded humans working at that scale to ensure things are moving the way they are supposed to. You'll want your company to have diversity of thought, and you'll want your ideas to be steel-manned to improve the chances of success. I don't think a growing headcount will be something people boast about in the future (in fact, I think, in the short-term hype cycle we're in, growing headcount will be seen as a negative), but I do think the number of small companies is going to explode. The more companies working on solving problems, the better chance they have of actually getting solved.

Let's first analyze how we got to where we are. When you're in a two-person company, direct communication is how communication happens. You don't need Slack or invites for internal meetings; you pick up the phone and talk. Direct communication is the most effective way to build and stay true to the vision set by the company's founders. You are, or are supposed to be, hyper-efficient. This amazing efficiency continues throughout the early growth, largely due to direct communication and the initial need to hire "ticket-makers" (your thought workers) rather than "ticket-takers" (your execution workers). You grow stably, and as you grow, direct communication gets offloaded to tools like Slack and email, and further gets offloaded through other employees who leverage the tools to communicate. Eventually, communication and decision-making that was once founder-only is distributed from the founders through layers of the organization to carry it out. Currently, the growth pattern/org-chart relationship is something like:

SizeLayersLeadershipStructure
102Founder(s)Everyone reports to a founder. No formal departments. One person often wears 3 hats.
302–3Founders + 1–2 leadsFirst functional leads emerge (Head of Eng, Head of Sales). First non-founder manager hired.
503CEO + 3–5 HeadsClear departments form. First HR/People hire. CEO starts losing visibility into individual work.
1003–4CEO + 5–7 VPsFull exec team in place. Directors appear beneath VPs. Formal onboarding, performance reviews, OKRs.
2004CEO + 6–8 VPsDirector layer fully established. Middle management is real. Chief of Staff or COO often added.
5004–5CEO + 8–10 C-suiteTrue C-suite (CMO, CPO, CRO). Sub-functions split (e.g., Sales → Enterprise/SMB). Internal comms function.
10005–6CEO + C-suite + SVPsSVP layer inserted between C-suite and VPs. Business units or divisions may form. Dedicated strategy, BizOps, and internal tools teams.

Many of these positions are required to enable the company's progress. There is only so much data you can consume, and there are only so many actions you can take in 24 hours. Delegating work across these layers becomes necessary to sustain growth. But, what if a founder did NOT have a limit to data consumed and did NOT have a limit on actions they could take in 24 hours?

This is what AI gives us the opportunity to change. We can build companies where some of the founders' decision-making processes are hardcoded into an agent, and that agent can be integrated into processes to reduce the need for multiple layers. We can build company knowledge stores that are accessed via natural language and provide an up-to-date view of the company's capabilities. Combining those two things with internal processes and tools would allow us to shrink the organization and begin to maximize efficiency (not to mention marketing improvements, like building a Capabilities MCP server on top of your knowledge store that broadcasts what your company is capable of and what work it has already done).

I think we should next look to group the responsibilities in our organization and see what information is needed to execute those responsibilities effectively. That can help tell us which agents to build and what data to collect.

For this post, I’ll start by focusing on what AI is good at, so we can understand what agents we need to build and how a company with these agents will be structured. Can we compress headcount so that the work of a traditional 1000-person company can be done by fewer than 100 people?

I’ve been building my own software factory to investigate the limits of AI agents today. I have deferred all coding to AI so I can better understand its strengths and weaknesses and how to bridge the gap to make it more reliable. To apply this to rethinking a company, we need to stop thinking of AI as simply executing tasks and instead consider how task execution can be strategically aligned with the company’s goals. Once we do that, we can identify the failure modes and specific capabilities that shape the company, which is very different from how today’s companies operate.

In building the software factory, I’ve started to build around the idea that AI is really good at 4 critical things:

  1. Information Routing. AI can be really good at taking some information and assigning it to an individual bucket from a set of buckets. So, passing the information and having it accurately determine where to put it is good.
  2. Information Summarization. This is pretty much out-of-the-box, good at summarizing. With a little structured prompting, it can be great at summarizing for an intended audience (i.e., a medical summary for a neurosurgeon).
  3. Pushing data into a specification. I’ve proposed the CAIL process as a replacement for AGILE. CAIL focuses on creating contracts that steer the AI toward an expected output and structure. AI is really good at taking unstructured or structured information and converting it into a specification.
  4. Following instructions when given a good context. The frontier models are fantastic at this. If you give an AI a clear set of steps to follow or a decision tree to think through, then it can do a great job of following that.

If these are what AI is good at, then we can map existing responsibilities to one of these categories where possible. This would guide us on which agents we need to build, the context each needs, and the responsibilities we need to offload to humans to carry out.

Category 1: Information Routing

TaskFrom Role
Filtering personal emailAdmin Assistant
Scheduling meetingsAdmin Assistant
Organizing filesAdmin Assistant
Qualifying inbound leadsSDR
Escalating real bugs to engineeringTech Support
Ensuring departments communicateCOO
Tracking expenses (categorization)Bookkeeper
Prioritizing the engineering backlogProduct Manager

Category 2: Information Summarization

TaskFrom Role
Analyzing user feedbackProduct Manager
Analyzing web trafficMarketing Manager
Generating monthly P&L reportsBookkeeper
Generating reportsService Provider
Analyzing dataService Provider
Monitoring workflowsCOO
Running regular client check-ins (the prep + recap)CSM
Proactively surfacing value opportunitiesCSM

Category 3: Pushing Data Into a Specification

TaskFrom Role
Writing feature requirementsProduct Manager
Writing automated testsQA
Writing codeSoftware Engineer
Drafting contractsAccount Executive
Sending invoicesBookkeeper
Reconciling bank statementsBookkeeper
Writing blog postsMarketing Manager
Managing social mediaMarketing Manager
Running email newslettersMarketing Manager
Creating ad campaignsMarketing Manager
Sending cold outreach emailsSDR
Writing copyService Provider

Category 4: Following Instructions With Good Context

TaskFrom Role
Answering support ticketsTech Support
Resetting passwordsTech Support
Walking users through troubleshootingTech Support
Setting up appointmentsSDR
Onboarding new clientsCSM
Running product demosAccount Executive
Finalizing sales (mechanics)Account Executive
Verifying features match requirementsQA
Finding bugs before customers doQA
Deploying updatesSoftware Engineer
Managing databasesSoftware Engineer
Managing software subscriptionsCOO
Booking travelAdmin Assistant

After you sort work into those categories, what’s left is the work that needs human thinking and execution. We can group similar responsibilities and then assign them to new roles:

TaskOld RoleNew RoleWhy It Stays Human
Setting company goalsCEOPrincipalNo defined success spec to generate against.
Deciding what products/services to buildCEOPrincipalHigh-stakes judgment under deep ambiguity.
Defining the product roadmapProduct ManagerPrincipalDeciding what the summarized feedback means.
Final say on resource allocationCEOPrincipalAccountability has to land on a person.
Optimizing internal processes (the "is this right" call)COOPrincipalJudgment about whether the system itself is correct.
Forming strategic partnershipsCEOCounterpartTrust between principals.
Client retention (the relationship)CSMCounterpartPerson-to-person trust.
Negotiating non-trivial pricingAECounterpartReading the room; downstream consequences.
Service execution (judgment-heavy parts)Service ProviderCrafterWhere taste and expertise matter.
Reviewing system architecture (final call)Software EngineerCrafterLong-tail tradeoffs.
Deciding what's worth testingQACrafterRisk judgment depending on business context.
Cash flow decisionsFinanceStewardWhere the money goes is an accountability call.

This becomes really intriguing because it removes the communication layer we needed the middle to provide and restructures the company to move at the speed of the knowledge layer, with people who have more agency. This means we can rethink our scaling table to be less dependent on the communication/oversight boundaries and instead be based on problem complexity. This unlinks headcount from growth. Headcount grows much more slowly, with principals growing in proportion to the problems the company solves, while crafters/counterparts can be distributed across multiple problems. The company degrades differently because failure modes shift from communication breakdowns to judgment failures. The tradeoff is with accountability. A company’s success or failure depends on the judgment and execution of its principal.

If we apply this new thinking to our previous table on company scaling, I can see massive productivity gains with far fewer people. There are still failure points, but they seem to be much narrower than in a traditional company:

ScopeHumansShapeWhat the AI Layer HandlesWhat Breaks at This Scale
Single problem, single customer type1–3One Principal wearing all four hats. Everything else is agents.Routing, summarization, spec generation, instruction-following — full stack.Nothing yet. The Principal is the bottleneck on judgment, but judgment volume is low.
Single problem, multiple customer segments3–6Principal + 1–2 Counterparts (one per major segment) + 1 Crafter for the core domain.Same as above, plus per-segment context maintained in the knowledge layer.The Principal starts to lose fidelity to the customer signal. First Counterpart hire fixes this.
Multi-faceted problem, one market6–12Principal + Counterparts for each relationship surface + Crafter for each domain where quality matters (eng, the service itself, maybe design). Steward responsibilities still held by the Principal.Cross-domain coordination via the knowledge layer. Agents handle hand-offs between Crafter.Taste calls start conflicting across domains. Need a forum (not a layer) for Crafter to align.
Multi-faceted problem, multiple markets12–25Multiple Principals (one per market or product line) + Counterpart pool + Crafter pool + dedicated Steward.Cross-market intelligence, consolidated reporting, resource flow visibility.Principals start to disagree on direction. Need an explicit mechanism for resolving cross-Principal conflicts — this is the first place a "layer" almost re-appears, and resisting it is the hard part.
Multiple problems, multiple markets25–60Federation of Principal-led units, each looking like the row above, sharing a common knowledge layer and agent infrastructure. One Principal-of-Principals or rotating council.Cross-unit knowledge transfer, shared agent infrastructure, capability broadcasting (your MCP idea).The shared infrastructure itself becomes a thing that needs its own Crafter. This is where the AI-native company hires its first "internal tools" humans, and the knowledge layer becomes load-bearing enough to require its own Steward.
Platform / ecosystem scale60–150Multiple federated units + a dedicated infrastructure unit maintaining the knowledge and agent layers + external-facing Counterparts at the ecosystem level.Everything the units do internally, plus ecosystem-level coordination with partners, developers, and regulators.At this point, you're approaching the size of a traditional 1,000-person company in terms of what it can do, with roughly 10–15% of the headcount. The failure mode is no longer structural. The failures will happen if Principals can't keep up with the volume of judgment calls. To resolve this, you'd need to add Principals or accept slower decisions.

The bet underneath all of this is that companies are slow because information moves inefficiently through layers of humans, and that if you replace the routing layer with software, the company starts moving at the speed of its knowledge layer instead. That's how 60 to 150 humans end up doing the work of a thousand; not because the humans are working harder, but because the distance between a decision and its execution collapses to nearly zero.

This isn’t a magic wand, though. The new structure has new problems, albeit different ones. When Principals are the only judgment layer in the company, there’s nothing above them to catch a bad judgment before it propagates. The current org charts include built-in human structures to mitigate that risk, which are missing from this new version. There’s still a significant gap that needs to be addressed. We need a different mechanism for catching judgment errors, and it needs that mechanism to work in something close to real time.

I started this series thinking every company would need a software factory. I'm now convinced it also needs a tiered knowledge dashboard. Traditional org charts catch bad judgment through layers: your manager sees your emails, their boss identifies patterns, and so on, until somewhere up the chain, a wrong decision gets caught or softened. An AI-native company doesn't have those layers, so it needs a mechanism to live elsewhere. The dashboard is where it lives: a real-time view of what Principals are deciding, their reasoning, and the outcome. It's a status report and an escalation path, and it has to be both because the layers that used to provide each separately are gone. We can dig into that in a future post.