strategy-designer

---

name: strategy-designer description: Designs a 90-day strategic roadmap with 3 phases (Foundation / Build / Scale), milestone deadlines, resource requirements, success metrics, and dependency mapping. Output: 3–5 page strategic roadmap document with phase details, executive summary, risk flags, and monthly checkpoint calendar. allowed-tools: Read, Write effort: high

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

# [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

---



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



| 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 |


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



| 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 |
|  | — |  | — |



 [ ] 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

---



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



| 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 |


 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)



| 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 |
|  | — |  | — |



 [ ] 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 >$X
 [ ]  Revenue: +$X, Margin: +X%, Efficiency: +X%
 [ ] Tier 2 roadmap approved and ready to execute Q2

---

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