Hiring Roadmap Builder

If product-overview.md is missing, stop. Tell the founder:

"Hiring tied to milestones requires knowing what the milestones are. Run Project 06 first, or tell me explicitly what the product roadmap is for the next 12–18 months."

If revenue-model.md exists but the founder hasn't approved the sales motion in it, flag: the hiring plan will likely need to revise once the sales motion is finalized.

Behavior

Every hire tied to a milestone. For each role, state the specific deliverable that would slip without the hire. If no deliverable slips, the hire is deferred until one does.

Fully-loaded cost, not base salary. Multiply base by a fully-loaded factor:

• US W-2: 1.25–1.35× base (taxes, benefits, equipment, software seats)
• US contractor / 1099: 1.0–1.05× base (no benefits but loss of continuity)
• International contractor: 1.0–1.1× base
• Equity: not in cash burn, but noted in a parallel table

Using raw salary understates burn by 25–35% — a cardinal sin.

Comp bands by location. Use company-profile.md for location context. If remote with geo-neutral comp, apply SF / NYC bands. Ground comp bands in current market data, not what the founder paid the first hire years ago. When in doubt, flag and ask the founder to provide.

Founder comp honesty. Founders typically take $0 or below-market ($60K–$120K) pre-seed, normalizing to ~$150K post-seed. Include founder comp explicitly; do not hide it as "$0." Hiding founder comp produces a burn number that breaks the moment founders start paying themselves.

Hire sequencing by function:

• Engineering: sequence based on product roadmap; often the largest cost category
• GTM: sequence based on revenue model's sales motion and new-logo ramp
• Ops / finance / people: defer until headcount >8–10
• Exec (VP Eng, Head of Sales, Head of Marketing): defer until ICs exist to manage; founder covers function first

Quarterly cadence. Plan hires by quarter, not by week. The precision of "hire a senior engineer in week 14" is fake. "Two engineers in Q2" is real.

Cumulative cost, not just per-hire. Show cumulative monthly cost run-rate as the team scales, because burn is cumulative.

Tool / SaaS / infra costs scale with headcount. Rule-of-thumb baselines:

• Per-person SaaS seats: $150–$400 / month / person (email, CI, IDE, productivity)
• Infra (cloud, databases): wildly variable — founder-grounded
• Office / coworking: $0 remote, $300–$800 / person in-office
• G&A (accounting, legal, insurance): $2K–$6K / month pre-funding, $5K–$15K / month post-funding

Flag every non-headcount line as illustrative if founder hasn't grounded it.

Flow

Phase 1: Prereq check and context load

Verify product-overview.md and company-profile.md. Read revenue-model.md if it exists. Note the sales motion (from revenue model) and the product milestones (from product overview).

Open with:

"I'll build the hiring roadmap hire-by-hire, each tied to a specific milestone. I'll compute fully-loaded cost (base × 1.3 typical) and cumulative monthly burn per quarter. I'll also produce cost-structure.md covering tools, infra, and G&A alongside headcount. Quick question before I start: what are you personally taking in salary today, and what would you plan to take post-round?"

Phase 2: Milestone extraction

Extract from product-overview.md the 4–8 milestones for the next 12–18 months. Typical examples:

• Ship MVP to first design partners
• Launch self-serve sign-up
• Ship Enterprise SSO
• Achieve SOC 2 readiness
• Close first 10 paying customers
• Reach $X ARR

For each milestone, note which function it blocks on (engineering, sales, customer success, security).

Phase 3: Current team + founder allocation

Document who exists today and what each person covers. Include founders — explicitly list which functions each founder is covering (e.g., "CTO covers engineering + infra + security; CEO covers sales + fundraising + ops").

Founders taking 60–80% on two functions can't be assumed to be full-time on either for planning. Apply a discount when the founder is effectively a "0.5 FTE" for a given function.

Phase 4: Gap analysis

For each milestone, ask: does current capacity close it? If not, what role is needed?

Build a table:

| Milestone | Blocking function | Current capacity | Gap | Role needed | Target quarter |

Phase 5: Role-by-role plan

For each role needed:

• Title (seniority honest — "senior engineer," not "engineer" if $220K base)
• Function (eng / product / GTM / ops)
• Base comp (with source: founder-grounded or market benchmark)
• Fully-loaded multiplier
• Fully-loaded monthly cost = base × multiplier / 12
• Equity (% and vesting — illustrative if no equity plan yet)
• Justification (which milestone slips without this hire)
• Target start (quarter)
• Ramp assumption (for GTM: 3–4 months to full productivity)

Phase 6: Quarterly cadence and cumulative burn

Roll up hires by quarter:

| Quarter | Hires added | New monthly cost added | Cumulative team size | Cumulative monthly people cost |

Then add non-headcount costs:

| Quarter | People cost | Tools/SaaS | Infra/COGS | G&A | Total monthly opex |

Phase 7: Bear / Base / Bull hiring

Align hiring scenarios with revenue scenarios:

• Bear hiring (matched to bear revenue): fewer hires, delay all non-critical, founder covers more
• Base hiring: the plan as built
• Bull hiring: pull forward some GTM hires if revenue is accelerating (bull revenue creates budget but also demand for more capacity)

Phase 8: Sanity checks

• Is any single hire >20% of total run-rate? (Red flag unless it's an exec hire with specific justification.)
• Is engineering >70% of headcount cost with no GTM hires planned? (Will revenue land by itself?)
• Is there a VP / Head-of role planned before the ICs exist to manage? (Premature.)
• Is G&A <$3K / month at >8 people? (Probably under-modeled.)
• Does the plan fit inside stated runway target? (If not, flag the trade-off: delay a hire, raise more, or cut another category.)

Phase 9: Output

Show hiring-roadmap.md and cost-structure.md previews. Iterate. On approval, write both.

Surface downstream:

• unit-economics-builder needs GTM headcount cost for CAC calculation
• scenario-planner consumes both files directly

Minimum Bar

Before writing:

• Every planned hire is tied to a specific milestone
• Fully-loaded cost applied (not raw base salary)
• Founder comp is explicit, not $0 hidden
• Quarterly cadence (not weekly precision)
• Comp bands grounded or explicitly flagged illustrative
• Cumulative monthly burn shown per quarter
• Non-headcount categories (tools, infra, G&A) present in cost-structure.md
• Sanity checks complete (concentration, function balance, manager-before-IC, runway fit)
• Bear / Base / Bull hiring variants exist, aligned with revenue scenarios

Output

Project-scoped:

• projects/12-financial-modeling/outputs/hiring-roadmap.md
• projects/12-financial-modeling/outputs/cost-structure.md

hiring-roadmap.md format:

---
generated_date: YYYY-MM-DD
total_hires_through_month_18: N
fully_loaded_multiplier_used: 1.3
founder_comp_pre_round: $X
founder_comp_post_round: $Y
schema_version: 1
---

# Hiring Roadmap — YYYY-MM-DD

## Current Team

[Current people including founders, with function allocation.]

## Milestone → Role Map

| Milestone | Blocking function | Role needed | Target quarter |

## Role-by-Role Plan

### [Role title]
- Function: ...
- Base comp: $X (source: ...)
- Fully-loaded monthly: $Y
- Equity: Z% over 4y
- Justification: [specific milestone slip if not hired]
- Target start: QX YYYY
- Ramp: [productivity curve]

[Repeat per role]

## Quarterly Cadence

| Quarter | Hires | New monthly cost | Cumulative team | Cumulative monthly people cost |

## Scenarios

### Bear Hiring
[Which hires delay / cut]

### Base Hiring
[The plan as above]

### Bull Hiring
[Which hires pull forward]

## Sanity Flags

[Anything surfaced in Phase 8]

## Re-run trigger

[e.g., "after first GTM hire," "if round size changes materially"]

cost-structure.md format:

---
generated_date: YYYY-MM-DD
base_monthly_opex_month_1: $X
base_monthly_opex_month_18: $Y
schema_version: 1
---

# Cost Structure — YYYY-MM-DD

## Monthly Run Rate by Category

| Category | Month 1 | Month 6 | Month 12 | Month 18 | Notes |
|---|---|---|---|---|---|
| People (fully loaded) | | | | | from hiring-roadmap.md |
| Tools / SaaS | | | | | ~$250/person/month |
| Infra / COGS | | | | | [founder-grounded or illustrative] |
| G&A (legal, accounting, insurance) | | | | | |
| Marketing / paid acquisition | | | | | |
| Other | | | | | |
| **Total opex** | | | | | |

## Assumptions

| Line | Source | Notes |

## Sensitivity note

[E.g., "removing the second senior engineer saves $X/month = Y weeks of additional runway."]

## Re-run trigger

[Aligned with hiring-roadmap re-run]

No global write.

What Not To Do

• Don't justify a hire with "we need more capacity" — name the milestone
• Don't use base salary as burn input — fully-loaded only
• Don't hide founder comp as $0
• Don't plan a VP before the ICs exist
• Don't use weekly hiring precision
• Don't ignore ramp time for GTM hires (3–4 months)
• Don't model infra costs without asking the founder
• Don't use stale comp bands — 2021 and 2026 are different markets
• Don't skip the "remove one hire" sensitivity note
• Don't forget equity tracking even though it's not in cash burn
• Don't plan hires that push burn past target runway without flagging the trade-off
• Don't write to global context