More people or a better system?

Quick reminder — Boardroom fall cohort applications are still open. If you're at $1M–$3M ARR and want a room of real peers at the same stage, applications are open. Short form. We review every one.

The first five founding members get three things the members after them won't:

→       A say in how the Boardroom is structured — format, cadence, focus areas

→       A free AI Visibility Audit for their agency — where your brand shows up (or doesn't) inside ChatGPT, Perplexity, Gemini, and Google AI Overviews

→       Quarterly 1:1 roadmap sessions with me, separate from group sessions

Here's how most agency hiring decisions happen:

The founder is overwhelmed. Something is breaking — too many client requests, too slow on delivery, too much still sitting on their own plate. They decide they need help. They write a job description. They hire someone.

Six months later, the new person is doing the work, but the founder is still overwhelmed. The bottleneck moved slightly — but it didn't resolve.

The hire didn't fix the problem because the problem wasn't a capacity problem. It was a systems problem.

Most agency hiring decisions are made reactively, in the middle of a capacity crunch, without a clear picture of what the person would actually do or whether the role needs a human at all. The result is expensive: the wrong hire, a vague role, or a human being paid to do work that a well-designed workflow could handle automatically.

This issue is about making better hiring decisions — which sometimes means hiring, and sometimes means building instead.

The question most founders ask when they're overwhelmed: "Who do I need to hire?"

The better question: "What is actually causing the bottleneck — and is a hire the right solution?"

There are three distinct problems that feel like capacity problems but aren't:

Problem 1: A systems problem disguised as a headcount problem.

Work keeps piling up not because there aren't enough people but because the workflow is broken — tasks aren't defined, handoffs are unclear, the same questions get answered repeatedly, and the founder is a required step in processes that shouldn't need them. Adding headcount to a broken system doesn't fix the system. It usually makes it more expensive and more complicated.

Problem 2: A scope problem disguised as a capacity problem.

The agency is at capacity because it has taken on more than it can deliver at the current team size — often because scope wasn't controlled, work expanded past what was agreed, or pricing wasn't adjusted to reflect delivery cost. Hiring to solve a scope problem means paying team costs to subsidize underpriced or poorly scoped work. The math gets worse, not better.

Problem 3: An AI gap disguised as a hiring need.

This is the newest version of the problem and the one most founders haven't fully reckoned with yet. A significant portion of the work that agency teams currently do — first-draft content, basic research, status updates, report generation, intake processing — can be handled at the execution layer by AI. Hiring a full-time human for a role where 40–60% of the day-to-day tasks are AI-handleable within 12 months is expensive, and it often means hiring someone into a role that's going to change significantly under them.

Before posting any role, pass every hiring decision through these three gates in order. A decision that clears all three is a genuine hire. A decision that fails any gate is a signal to look at the underlying problem first.

GATE 1  Is This a Capacity Problem or a Systems Problem?

Map the bottleneck before you map the role. Ask: if this workflow were fully documented and the most repetitive steps were automated or handled with AI, would you still need to hire? If the answer is "maybe not" — fix the workflow first. Then reassess.

How to tell the difference:

Capacity problem: you have a clearly defined workflow, everyone knows what to do, there simply aren't enough hours in the day to do it all. The fix is headcount.

Systems problem: work stalls, gets re-done, or sits in someone's inbox waiting for a decision. The same questions get asked repeatedly. You're a required step in things that shouldn't need you. The fix is workflow design — before anyone new joins.

GATE 2  What Would This Person Actually Do?

Write down the 10 most common tasks the person in this role would do in a typical week. Not the job description — the actual work. What does a Tuesday afternoon look like for them?

This exercise reveals two things most founders don't see until they do it: the role is often either much narrower than they thought (it's really just one or two core functions), or much more senior than they're prepared to hire for (it requires judgment and context they'd spend a year transferring).

If you can't write the task list before you post the role, you're not ready to hire. The vagueness isn't a hiring problem — it's a clarity problem.

GATE 3  What Could AI Handle in This Role?

For every task on your list from Gate 2, ask: could AI handle the execution of this if the workflow were designed properly? Not "could AI write something generically" — specifically: if you built a Claude Project with the right context, or connected an automation to the right data, could this step run without a human doing it?

If 50% or more of the tasks in the role you're considering are AI-handleable today or within 12 months — you have a choice. Hire someone into the full role and plan to reshape it as AI adoption increases. Or design the AI-native version of the role first, hire for the genuinely human parts, and give that person significantly more leverage from day one.

The second option is almost always better. And it starts with the workflow design, not the job posting.

If you have a role in mind right now — or even a vague sense that you need to hire someone — do this before you write the job description.

Gate 1 check (30 min):

Write down the workflow that's creating the bottleneck. Map the current steps. For each step: is this a capacity problem (not enough hours) or a systems problem (broken process, unclear handoff, founder dependency)? If you find more than two systems problems, fix those before posting any role.

Gate 2 check (20 min):

List the 10 most common tasks the person in this role would do in a typical week. Be specific and honest. If you can't fill in 10 tasks, you're not ready to hire — spend the time getting clear on the role first.

Gate 3 check (20 min):

For each task, mark: AI-handleable today / AI-handleable in 12 months / Genuinely human-required. Count the percentage in each column. If more than 50% is AI-handleable today or soon, design the AI-native version of the role before you hire.

A hire that passes all three gates is a genuine hire. A decision that fails any gate is an invitation to solve the real problem first.

Most job descriptions are written from a place of urgency — and it shows. They're vague on day-to-day tasks, aspirational on qualifications, and missing the operational context a good candidate would need to decide if the role is right for them.

Here's a prompt that uses Claude to design the role properly before you write the description — which also forces the clarity that Gate 2 requires.

The conversation the prompt generates is often more valuable than the job description itself — because it forces you to answer the questions most founders skip when they're operating from urgency.

The best person for your next role might not live near your office—or even in the same country.

More companies are realizing they don't need to open entities everywhere just to access global talent. Instead, they're using EOR to hire internationally faster, stay compliant, and avoid building local infrastructure before they're ready.

Oyster's EOR helps companies hire, pay, and support employees in 180+ countries while Oyster handles payroll, compliance, taxes, and local employment requirements.

See how it works

This week's picks are oriented around smarter hiring — finding better candidates, running better processes, and managing team performance once someone's in the seat.

Ashby  ashby.io

Modern ATS (applicant tracking system) built for teams that hire carefully rather than at volume. Cleaner interface than Greenhouse or Lever, with AI-powered candidate scoring and a free tier for smaller teams. What sets it apart for agencies: it's designed around quality over speed — structured scorecards, interviewer guides, and team feedback consolidation so hiring decisions are made on evidence rather than gut feel. Used by Linear, Vercel, and Notion. Free up to 10 open roles.

Pave  pave.com

Compensation benchmarking and planning platform that lets you see what comparable roles pay in real time — by geography, company size, and funding stage. For agencies making their first or second hire at a senior level, Pave removes the guesswork from salary setting and prevents the two most common mistakes: underpaying (candidate declines, you restart) and overpaying (margin hit, precedent set). Free to benchmark individual roles; paid for team planning features.

Kula AI  kula.ai

AI recruiting automation that finds candidates across LinkedIn, GitHub, and portfolio sites, then personalizes outreach at scale based on their work. For agencies doing occasional senior hiring without a dedicated recruiter, Kula compresses what would normally be 20–30 hours of sourcing and outreach into a few hours. Particularly good for creative and technical roles where portfolio signals matter. Connects to your ATS. Pricing on application.

Metaview  metaview.ai

AI interview notes that record and transcribe every candidate conversation without a visible bot in the room — similar to Granola's approach to meetings but purpose-built for interviews. Surfaces key moments, flags evaluation criteria, and produces a structured summary that can be shared across the hiring team. For agencies running interviews across multiple team members, it removes the "what did you think?" ambiguity and creates a consistent evaluative record. Free trial available.

Motion  usemotion.com

AI task and project management that automatically schedules your workday, defends focus time, and reprioritizes dynamically when things change. Relevant here because capacity is the most common trigger for a hiring decision — and Motion is worth running for 30 days before committing to a hire. If workload gets significantly more manageable with AI-assisted scheduling, you may not be as understaffed as you thought. $19/month individual; $12/user/month for teams.

📊 BY THE NUMBERS

$15,000-$25,000

That's the estimated cost of a bad hire at the mid-level (account manager, strategist, senior writer) when you factor in recruiting time, onboarding investment, reduced team productivity during ramp, severance if applicable, and the restart. For senior roles the number is higher.

The agencies with the best hiring records aren't the ones who hire fastest. They're the ones who spend the most time on the decision before posting the role — defining what they actually need, running the task analysis, and being honest about whether a human or a system is the right solution. The 3-gate check takes 70 minutes. A bad hire costs 70 hours of cleanup plus $15,000 in hard costs.

TL;DR: Fall cohort applications now open for Boardroom, our version of a mastermind. Real peers, real accountability, and direct advisory access at a stage of business where most owners say that's the hardest thing to find. For PR + marketing agency owners generating $1-3M ARR. [APPLY FOR FOUNDING MEMBER OFFER]

See you next week.

Work smart. Enjoy life harder.

Founder, Agency Owner Lab

When you're ready, here's how we can work together:

→ The Boardroom — Get in the right room. for PR + marketing agency founders generating $1-3M ARR. Advisory, peer accountability, exclusive partner offers/resources. Applications now open for Fall cohort! [Apply here]

→ Agency AI Adoption Assessment + Engagement — Custom AI strategy for your agency. Plus option to add 3 months of fractional ops support to make sure adoption sticks. [Apply here]

→ Agency Growth Roadmap — Operational audit + systems strategy. [Apply here]

→ Founder Advisory — Your advisor. Your business partner. For the founder who uses AI for strategy but wants a real human to strategize with. Quarterly commitments. Agencies doing 20k/month - approaching 7 figures [Apply Here]

→ Implementation Sprints — done-for-you systems builds, Standalone or paired with another program. [Book a Systems Audit]

→ Agency OS Lab (Community Membership) — SOPs, Claude installs, tool stacks. $97/month. [Join the waitlist here]