Herb — Org Chart Architecture

Current State

Everyone reports to Matt. Zero layers.

CEO / Founder

Matt Gray

Vision + content + clients + hiring + approvals + ops

Content

~8 people

Writers, editors, designers

Agency

~10 people

AMs, producers

Operations

~7 people

Admin, finance, tools

25+ people · 1 decision-maker · 0 layers · This is the bottleneck

Founder Dependency Audit

What Matt is doing today that should be delegated

40%

Client management — calls, deliverable reviews, escalations. → Head of Agency

20%

Content approvals — every post routes through Matt. → Head of Content

15%

Hiring — screening to final interview, every role. → Head of Ops

10%

Tools & systems — choosing, configuring, troubleshooting. → Head of Ops

10%

Finance — invoices, budgets, cash flow. → Head of Ops

Team management — 15+ 1:1s. → 3 leads handle their teams

Recommended Structure

3 direct reports. 3 departments. Founder removed.

CEO / Founder

Matt Gray

Vision · anchor content · 3 check-ins/week

Head of Content

Promote within

Strategy, approvals, waterfall

Head of Agency

To Hire — #1

Delivery, accounts, results

Head of Ops

Claire

Hiring, finance, SOPs

~8 · Writers, editors, video

~10 · AMs, strategists

~5 · Admin, finance, recruiting

Role Scorecard

Head of Content

Promote from within · Reports to Matt · FT

Own the content engine so Matt only creates anchor pieces. Every post published on time, on brand, without Matt in the approval chain.

Responsibilities

Content strategy & calendar
Quality approvals (95% without Matt)
Content Waterfall: 1 → 25+ assets
Team management: writers, editors, design

Decision Authority

Post approvals — full authority
Video edits — full after calibration
Content calendar — full
Escalate: direction changes, new platforms

Role Scorecard · Priority Hire #1

Head of Agency Services

External hire · Reports to Matt · FT · $120-150K/yr

Own client delivery end-to-end so Matt only appears for quarterly strategy reviews. Every client onboarded, serviced, and retained without the founder.

Responsibilities

Client delivery & satisfaction
Account management & reporting
Agency team performance
Productize delivery into SOPs

Ideal Candidate

5+ yrs agency ops ($3-10M scale)
Managed 8+ person delivery team
Built SOPs & productized services
Calm, high ownership, low ego

Role Scorecard

Head of Operations

Claire (or equivalent) · Reports to Matt · FT

Run the operational engine without Matt. Own hiring, finance, tools, and systems so the business scales with predictability and calm.

Responsibilities

Hiring & recruiting end-to-end
Finance, budget, vendor management
Tools, systems, internal SOPs
Team culture & HR

Decision Authority

Full hiring process (Matt meets senior finals)
Expenses under $500/mo — no approval
Tool decisions — full authority
Escalate: budget >$2K, comp changes

Founder Scorecard

Matt Gray — CEO

4 hours/day max · 3 direct reports · Vision + content only

Matt Does

Record 1 YouTube video/week
3 weekly check-ins (30 min each)
Quarterly client strategy reviews
Monthly P&L review (1 hour)
Vision, partnerships, brand direction

Matt Does NOT Do

Approve posts or content
Manage client accounts
Screen or interview (non-senior)
Choose tools or configure systems
Review invoices or manage budgets

Meeting Rhythm

From chaos to 3 hours of structured meetings per week

Leadership Sync

Weekly · 60 min · Matt + 3 leads

Wins from last week
Key metrics per lead
Top 1-2 issues per lead
Decisions needed from Matt
This week's priorities

Content Review

Weekly · 30 min · Head of Content → Matt

Performance: views, engagement
Next week's calendar preview
Anchor content plan
Creative direction questions

Agency Check-in

Weekly · 30 min · Head of Agency → Matt

Client health dashboard
At-risk accounts
Delivery pipeline status
Revenue per client update

Ops Check-in

Weekly · 30 min · Head of Ops → Matt

Hiring pipeline status
Financial summary (1 page)
Tools/systems updates
Team health flags

Quarterly OKRs · Q2 2026

Matt Gray — CEO

Transition from operator to architect

Reduce direct reports from 15+ to 3 within 30 days

80%+ time on content, strategy, and partnerships

Zero daily content or client approvals

Scale revenue while working less

Revenue growing quarter over quarter

4-hour max workday by end of quarter

Team health score 8+/10 (anonymous survey)

Quarterly OKRs · Q2 2026

Head of Content

Own the content machine

25+ assets published per week, 100% on schedule

Brand Voice Checklist created and calibrated within 14 days

Matt's daily content approvals reduced to zero

Drive measurable results from content

Content-attributed leads tracked and growing MoM

Weekly performance report running consistently

Quarterly OKRs · Q2 2026

Head of Agency Services

Own client delivery end-to-end

Client retention 90%+ for the quarter

Matt's client-facing time reduced by 80%

All delivery SOPs documented by end of quarter

Build a repeatable service machine

Client onboarding time under 48 hours

Monthly client scorecards running

Quarterly OKRs · Q2 2026

Head of Operations

Self-running operational engine

All open roles filled within 30 days

Weekly financial summary running every Monday

All critical SOPs documented and current

Build team health infrastructure

Team satisfaction 8+/10 (quarterly anonymous survey)

Ops cost as % of revenue: stable or decreasing

Hiring Roadmap

Sequenced by constraint — each hire unlocks founder removal

NOW

Head of Agency Services

The #1 constraint. Frees 15-20 hrs/week. $120-150K/yr. Matt's time redirected to vision generates 3-5x ROI.

30 DAYS

Promote Head of Content

Strongest content team member. Title + authority + Brand Voice Checklist. $15-25K bump. Matt exits content approvals.

60 DAYS

Formalize Head of Ops

Claire (or external). Full authority over hiring, finance, systems. $100-130K/yr. Matt exits all operational decisions.

90 DAYS

Evaluate: Fractional CFO

Assess once 3-layer structure is running. Needed as revenue scales past $8M.

Delegation Playbook

Matt's handoff plan — clear owners, clear timelines

DAY 1-14

Client accounts → Head of Agency

Document all relationships. Introduce new lead. Shadow 2 weeks. Matt joins quarterly reviews only.

DAY 1-14

Content approvals → Head of Content

Create 10-point Brand Voice Checklist. Head of Content approves 95%. Matt reviews anchor pieces only.

DAY 1-30

Hiring → Head of Ops

Ops owns JDs, sourcing, screening, first interviews. Matt meets finals for senior roles only.

Delegation Playbook

Continued

IMMEDIATE

Tools & systems → Head of Ops

Full authority under $500/mo. Above $500, 2-minute decision in weekly check-in.

DAY 1-14

Finance → Head of Ops

Weekly 1-page summary every Monday. Monthly P&L review only. No invoices, no micro-management.

DAY 1-30

Team 1:1s → Department Leads

Each lead owns their team's 1:1s, performance, and growth. Matt does 3 lead check-ins, not 15+ team 1:1s.

Next Steps

Clear actions. Clear owners. Start Monday.

Write the Head of Agency job description

Use the role scorecard. Post on LinkedIn, Dynamite Jobs, Talent OS. Target: 10 candidates in 14 days.

Identify your Head of Content

Strongest content team member. Promote them this week. Give title, authority, and the quality checklist.

Create the Brand Voice Checklist

10-point quality gate. Head of Content approves 95% without you. We can build this as a deliverable.

Formalize Claire's authority

Make it official. Define decision authority, budget thresholds, reporting rhythm.

Schedule your first Leadership Sync

60 min, weekly, all 3 leads. Use the agenda above. Replaces 15+ ad-hoc conversations.

Set the 90-day review

Book it now. Score every OKR 0-1.0. Evaluate the structure. Plan the next phase.