Commercial CTO Consulting

Joseph is an independent CTO consultant (proprietor). This skill activates when he discusses commercial work — reviews, new initiatives, solution formulation, VC due diligence, or coaching.

Before Any Commercial Work

Always read the relevant context file first:

[client]: wiki/wealth/consulting/[client]/_context.md
VC / due diligence: wiki/wealth/consulting/vc/_context.md
Coaching: wiki/wealth/consulting/coaching/_context.md

These files contain engagement details, org structure, tech landscape, and active initiatives. Without them, you're working blind.

Directory Map

wiki/wealth/consulting/
├── [client]/
│   ├── _context.md              ← Always load first
│   ├── reviews/                 ← Architecture, code, process reviews
│   ├── initiatives/             ← New initiative evaluations, proposals
│   ├── solutions/               ← Solution designs, ADRs, tech choices
│   └── monthly/                 ← Monthly deliverables, summaries
├── vc/
│   ├── _context.md              ← VC relationships + evaluation framework
│   └── due-diligence/           ← Per-company tech assessments
├── coaching/
│   ├── _context.md              ← Coaching relationships
│   └── engagements/             ← Per-client coaching notes
├── invoices/                    ← Invoice generation + tracking
├── rates.md                     ← Rate card
└── [client]/                    ← [client] client work

Workflows

1. Review (architecture, code, process, SOW)

When Joseph asks for a review:

1. Read the relevant _context.md — what's the company context, tech stack, constraints?

2. Read the document/code being reviewed

3. Write the review to the appropriate reviews/ subdirectory

4. Name convention: YYYY-MM-DD-<topic>-review.md

5. Structure the review: Summary → Findings → Recommendations → Risk Assessment

6. Ground every finding in the company's reality (size, team, clients, budget) — not generic advice

2. New Initiative / Proposal

When Joseph wants to evaluate or formulate a new initiative:

1. Read the _context.md for company constraints (budget, team, client base, strategic direction)

2. Write to initiatives/ with this structure:

Problem/Opportunity — what are we solving?
Strategic fit — does this align with the company's direction?
Market assessment — who else is doing this? what's the demand?
Capability gap — what do we need that we don't have?
Rough resource estimate — people, time, investment
Risk assessment — what could go wrong?
Recommendation — go / no-go / more investigation needed

3. Solution Formulation

When Joseph asks for solution design or technology recommendations:

1. Read the _context.md for existing tech landscape

2. Write to solutions/

3. Structure: Problem → Constraints → Options considered → Recommendation → Rationale → Implementation approach

4. Always consider: existing stack fit, team capability, operational overhead, cost

4. Monthly Summary

When Joseph wants a monthly summary:

1. Scan monthly/, reviews/, initiatives/, solutions/ for the month's work

2. Check session history for relevant conversations

3. Produce a summary: what was done, key decisions, open items

Pitfalls

Don't give generic consulting advice — every recommendation must be filtered through the company's actual size (~250 people, ₹30 Cr), client base (NA/UK), and constraints
Don't invent details — if _context.md has [FILL] placeholders, ask Joseph to fill them
Don't over-engineer — a ₹30 Cr services firm needs different solutions than a product company or FAANG
Joseph is fractional, not full-time — recommendations must account for him not being there day-to-day

After Each Session

Update _context.md if new facts emerged (initiatives, people, tech changes)
Save durable facts to Mnemosyne (company preferences, key decisions, recurring patterns)

commercial-cto