# Strategy Designer

> Strategy Designer

- Skill: `uitbreidenos/strategy-designer` (Agent Skill)
- Install (CLI): `npx skillmds@latest add uitbreidenos/strategy-designer`
- Raw SKILL.md: https://api.skillmd.com/api/skills/uitbreidenos/strategy-designer/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- Author: UitbreidenOS (https://skillmd.com/u/uitbreidenos)
- Updated: 2026-09-22
- Page: https://skillmd.com/skills/uitbreidenos/strategy-designer

---


# Strategy Designer

## When to activate
After identifying opportunities via opportunity-identifier. Use when client has approved the opportunity list and wants a detailed execution roadmap. Create before deal structuring or implementation.

## When NOT to use
Skip if engagement is diagnostic only (no execution planned). Skip if client needs lightweight advisory without formal roadmap.

## Instructions

### Step 1: Structure 3 Phases

**Phase 1: Foundation (Weeks 1–4)**
- Establish governance: assign owners, create steering committee
- Deep dive into top opportunities: refine business case, validate assumptions
- Baseline measurement: current metrics, benchmarks, capability gaps
- Build change management plan: stakeholder alignment, communication cadence

**Phase 2: Build (Weeks 5–8)**
- Pilot or launch Opportunity 1 (quick win)
- Begin Opportunity 2 and 3 (parallel tracks)
- Monitor metrics, adjust approach based on early signals
- Stakeholder updates: weekly tactical, bi-weekly strategic reviews

**Phase 3: Scale (Weeks 9–12)**
- Scale Opportunity 1 across organization
- Complete launch of Opportunity 2 and 3
- Prepare roadmap for Opportunity 4 (strategic bet)
- Review outcomes against success metrics

### Step 2: Define Milestones

For each phase, define 3–4 key milestones with owners and dependencies:

```
Phase 1 (Foundation): Weeks 1–4
├─ Week 1: Governance established, steering committee formed
├─ Week 2: Deep dive findings documented, assumptions validated
├─ Week 3: Baseline metrics locked, resource plan finalized
└─ Week 4: Change management plan approved by leadership

Phase 2 (Build): Weeks 5–8
├─ Week 5: Opp 1 pilot launched, team trained
├─ Week 6: Opp 1 initial results reviewed; Opp 2 development underway
├─ Week 7: Opp 1 expanded to broader team; Opp 3 initiated
└─ Week 8: Month 2 results reviewed; roadmap adjusted

Phase 3 (Scale): Weeks 9–12
├─ Week 9: Opp 1 scaled company-wide; Opp 2 nearing completion
├─ Week 10: Opp 2 launched; Opp 3 in final testing
├─ Week 11: All Tier 1 opportunities live; Opp 4 scoping underway
└─ Week 12: Final assessment; long-term roadmap established
```

### Step 3: Resource Requirements

For each phase and opportunity:
- **People:** FTE allocation by function (sales, product, marketing, ops)
- **External:** Consultants, contractors, technology costs
- **Timeline:** Calendar weeks, calendar months, Q notation
- **Budget:** Rough order of magnitude for phase

### Step 4: Success Metrics & Checkpoints

Define "Definition of Done" for each phase:

**Phase 1 Completeness:**
- All opportunity business cases validated
- Governance structure established and staffed
- Change management plan in place
- Baseline metrics locked

**Phase 2 Progress:**
- Opp 1 live and showing positive early signals (metrics on track)
- Opp 2 and 3 development >50% complete
- Team trained and performing against plan
- Steering committee engaged, no major blockers

**Phase 3 Success:**
- All Tier 1 opportunities live and meeting success metrics
- Financial impact realized (revenue, cost, efficiency) within 10–15% of plan
- Team capability uplifted and internalized
- Roadmap for Tier 2 approved and ready to execute

### Step 5: Risk & Dependency Mapping

Identify for each phase:
- **Critical Path:** Which opportunities are prerequisites for others
- **Bottlenecks:** Resource constraints, external dependencies
- **Risks:** Org alignment, market, execution, talent
- **Mitigation:** Contingency plans, escalation path

## Output Format

```markdown
# [Company Name] — 90-Day Strategic Roadmap

**Date:** YYYY-MM-DD  
**Engagement:** Strategic Advisory  
**Duration:** 90 days  
**Sponsor:** [C-level executive]

---

## Executive Summary

[2–3 paragraph summary: why this roadmap, what it achieves, what success looks like]

**Key Outcomes:**
- [Quantified outcome 1: revenue / cost / efficiency]
- [Quantified outcome 2]
- [Quantified outcome 3]

**Timeline:** [Start date] through [End date]  
**Steering Committee:** [CEO], [CFO], [Chief of Staff]  
**Check-in Cadence:** Weekly tactical (ops), bi-weekly strategic (leadership)

---

## Phase 1: Foundation (Weeks 1–4)

**Objective:** Establish governance, validate assumptions, baseline metrics, build change plan.

### Milestones

| Milestone | Owner | Deadline | Success Criteria |
|---|---|---|---|
| Governance established | [Owner] | Week 1 | Steering committee meets; decision rights clear |
| Deep dive complete | [Consultant] | Week 2 | Business cases refined; assumptions tested |
| Baseline locked | [CFO/ops] | Week 3 | Current-state metrics documented; benchmarks set |
| Change plan approved | [COO/HR] | Week 4 | Communication plan ready; training curriculum defined |

### Opportunities in Scope
- Opportunity 1: Foundation work (playbook design, stakeholder prep)
- Opportunity 2: Design phase underway
- Opportunity 3: Scoping and resource planning

### Resource Requirements

| Function | FTE | Cost | Notes |
|---|---|---|---|
| Sales Leadership | 0.5 | — | Steering committee + playbook design |
| Sales Enablement | 1.0 | $X | Design, train-the-trainer development |
| Product | 0.25 | — | Opp 2 technical scoping |
| Operations | 0.5 | — | Governance, tracking, baseline metrics |
| **External Consultant** | — | $X | Strategy, deep dive facilitation |
| **Total Phase 1** | — | **$X** | — |

### Success Metrics (Definition of Done)

- [ ] Governance structure documented and staffed
- [ ] Business cases validated; assumptions risk-rated
- [ ] Baseline metrics: [Current metric 1], [Current metric 2], [Current metric 3]
- [ ] Change plan includes stakeholder map, comms schedule, training plan
- [ ] Leadership alignment: CEO + steering committee sign-off on phases 2–3

---

## Phase 2: Build (Weeks 5–8)

**Objective:** Launch Opportunity 1 pilot; develop Opportunities 2 and 3; monitor early signals.

### Milestones

| Milestone | Owner | Deadline | Success Criteria |
|---|---|---|---|
| Opp 1 pilot live | [Sales VP] | Week 5 | 20% of team trained; pilot cohort identified |
| Opp 1 initial results | [Ops] | Week 6 | Early metrics positive; >85% of plan |
| Opp 2 launch | [Product] | Week 7 | Feature live; beta customers onboarded |
| Opp 3 development | [Marketing] | Week 8 | Campaign assets ready; list segmented |

### Opportunities in Scope
- Opportunity 1: Pilot expansion (40% of team)
- Opportunity 2: Build and beta launch
- Opportunity 3: Asset development, campaign preparation

### Resource Requirements

| Function | FTE | Cost | Notes |
|---|---|---|---|
| Sales | 2.0 | — | Full pilot execution + trainer support |
| Product | 2.0 | — | Opp 2 build and support |
| Marketing | 1.0 | — | Opp 3 campaign development |
| Operations | 1.0 | — | Metrics tracking, steering committee reporting |
| **Total Phase 2** | — | **$X** | — |

### Success Metrics (Definition of Done)

- [ ] Opp 1: [Metric 1] = [Target], [Metric 2] = [Target] (vs. baseline)
- [ ] Opp 2: >10 beta customers, NPS >40, product stable for broader rollout
- [ ] Opp 3: Campaign launch ready; [X% target audience] segmented
- [ ] No major blockers; team morale stable
- [ ] Steering committee alignment on Phase 3 plan

---

## Phase 3: Scale (Weeks 9–12)

**Objective:** Scale Opportunity 1 company-wide; complete launch of Opportunities 2 and 3; plan Tier 2.

### Milestones

| Milestone | Owner | Deadline | Success Criteria |
|---|---|---|---|
| Opp 1 full rollout | [Sales VP] | Week 9 | 100% of team trained; playbooks embedded in CRM |
| Opp 2 GA launch | [Product] | Week 10 | 100% of target customers migrated; support staffed |
| Opp 3 campaign live | [Marketing] | Week 11 | Demand generation live; lead flow >baseline |
| Month 3 results | [CFO] | Week 12 | Y-to-date impact = $X; success metrics met |

### Opportunities in Scope
- Opportunity 1: Full-scale rollout (100% of team)
- Opportunity 2: General availability, full support
- Opportunity 3: Active campaign, lead generation
- Opportunity 4: Scoping and business case refinement (Tier 2)

### Resource Requirements

| Function | FTE | Cost | Notes |
|---|---|---|---|
| Sales | 1.0 | — | Sustaining support; deal review and coaching |
| Product | 1.5 | — | Production support; roadmap planning |
| Marketing | 1.0 | — | Campaign optimization; lead scoring |
| Operations | 0.5 | — | Final metrics, handoff documentation |
| **Total Phase 3** | — | **$X** | — |

### Success Metrics (Definition of Done)

- [ ] Opp 1: [Metric 1] = [Target], [Metric 2] = [Target], company-wide adoption >90%
- [ ] Opp 2: [Metric 1] = [Target], customer satisfaction >80%
- [ ] Opp 3: [Metric 1] = [Target], new pipeline >$X
- [ ] **Total financial impact:** Revenue: +$X, Margin: +X%, Efficiency: +X%
- [ ] Tier 2 roadmap approved and ready to execute Q2

---

## Dependency & Critical Path Map

```
Phase 1:
├─ Governance & Steering Committee (prerequisite for all)
└─ Baseline Metrics (prerequisite for Phase 2 measurement)

Phase 2:
├─ Opp 1 Pilot (prerequisite for Phase 3 scale)
├─ Opp 2 Build (independent; supports Phase 3 launch)
└─ Opp 3 Development (independent; supports Phase 3 launch)

Phase 3:
├─ Opp 1 Scale (depends on Phase 2 pilot success)
├─ Opp 2 GA (depends on Phase 2 beta success)
├─ Opp 3 Campaign (depends on Phase 2 development)
└─ Opp 4 Planning (can start mid-Phase 3; launches Phase 2 of engagement)
```

**Critical Path:** Phase 1 → Opp 1 (Phase 2) → Opp 1 Scale (Phase 3)

---

## Risk Register & Mitigation

| Risk | Impact | Likelihood | Mitigation | Owner |
|---|---|---|---|---|
| [Risk 1: Low exec alignment] | High | Medium | Weekly steering committee; CEO sponsor visible in rollout | CEO |
| [Risk 2: Team resistance] | High | Medium | Change comms plan; train-the-trainer program; early wins celebration | COO |
| [Risk 3: Technical blocker] | Medium | Low | Design phase identifies; contingency in architecture | CTO |
| [Risk 4: Market headwind] | High | Low | Diversify opportunities; monitor competitor activity weekly | CMO |

---

## Month-by-Month Checkpoint Calendar

### Month 1 (Foundation)
- **Week 1:** Kickoff + governance setup
- **Week 2:** Deep dive findings shared with leadership
- **Week 3:** Baseline metrics locked; resource plan finalized
- **Week 4:** Change plan approved; Phase 2 prep begins
- **Executive Checkpoint:** Month 1 review; proceed to Phase 2?

### Month 2 (Build)
- **Week 5:** Opp 1 pilot launched (20% of team)
- **Week 6:** Opp 1 metrics reviewed; early wins celebrated
- **Week 7:** Opp 2 launch; Opp 1 expands (40% of team)
- **Week 8:** Month 2 results; fine-tune plan for Phase 3
- **Executive Checkpoint:** Month 2 review; on track to Phase 3?

### Month 3 (Scale)
- **Week 9:** Opp 1 full rollout (100% of team)
- **Week 10:** Opp 2 GA launch
- **Week 11:** Opp 3 campaign live; Tier 2 planning underway
- **Week 12:** Final results; long-term roadmap approved
- **Executive Checkpoint:** Engagement outcomes review; transition to next phase

---

## Engagement Transition

At Week 12 completion:
1. **Option A (Recommended):** Begin Phase 2 of engagement (Opportunities 4–5) on rolling basis
2. **Option B:** Pause and assess; resume in 30 days if needed
3. **Option C:** Transition to ongoing advisory (part-time, 4 hours/month)

**Success Definition:** All Phase 1–3 success metrics met OR contingency plan executed per risk register.
```

## Example

**Company:** B2B SaaS, $20M ARR, 85 employees  
**Engagement Length:** 90 days  
**Sponsor:** CEO (with CFO co-sponsor)

**Outcome Targets:**
- Opp 1: +$3M ARR in 6 months (sales efficiency)
- Opp 2: +$2M ARR in 12 months (SMB segment)
- Opp 3: +15% ACV, +5% margin (pricing model shift)
- **Total Year 1 Impact:** +$5M ARR, +5% margin expansion

**Phase 1 Focus:** Governance, deep dive, sales playbook design, SMB market research, pricing modeling

**Phase 2 Focus:** Sales playbook pilot (20% of team), SMB product design, pricing test with 3 customers

**Phase 3 Focus:** Sales playbook rollout (100%), SMB GA launch, pricing model shift across portfolio, Tier 2 planning