Chapter 14: Experience Strategy & Portfolio

Executive Summary

An Experience Strategy translates business objectives into a coherent plan for delivering customer value across all touchpoints—product, website, support, and customer success. Unlike feature roadmaps (which list what to build), an experience strategy defines how different customer segments will achieve outcomes through orchestrated journeys spanning multiple products, channels, and lifecycle stages. In B2B IT, where companies often have product portfolios (core platform + add-ons, mobile + web, multiple market segments), experience strategy answers: Which segments do we serve? What outcomes do they need? How do products, channels, and touchpoints work together? This chapter shows how to craft a segment-based experience strategy linked to OKRs, prioritize experience investments, and govern a portfolio to prevent fragmentation while enabling innovation—ultimately driving retention, expansion, and market differentiation.

Definitions & Scope

Experience Strategy

A deliberate plan for how customer segments will achieve desired outcomes through orchestrated experiences across products, channels, and lifecycle stages. Components:

1. Segments & Outcomes: Who we serve, what outcomes they need.
2. Experience Themes: Strategic bets (e.g., "Mobile-first field operations," "AI-assisted analytics").
3. Portfolio Architecture: How products/features fit together (core + add-ons, bundles, platform).
4. Channel Mix: Where experiences happen (mobile, web, desktop, email, support, CS).
5. Investment Allocation: Budget/resources per theme, segment, product.

Experience Portfolio

The collection of products, features, and touchpoints a company offers. B2B portfolios often include:

• Core Platform: Central product (e.g., analytics platform, CRM, project management).
• Add-Ons/Modules: Optional features (e.g., advanced reporting, API access, integrations).
• Multi-Product: Separate products sold together (e.g., marketing automation + CRM).
• Multi-Channel: Same product across channels (web, mobile, desktop app).
• Multi-Segment: Tailored experiences for segments (Enterprise vs SMB, industry verticals).

Strategy vs. Roadmap

• Strategy: Why, who, what outcomes (strategic direction, 1–3 years).
• Roadmap: What features, when (tactical execution, quarterly/annual).
• Strategy drives roadmap (not vice versa).

Scope

This chapter applies to B2B IT product/design leaders, CPOs, VPs Product, and cross-functional teams (PM, Design, Eng, CS, Marketing). Covers strategy formulation, portfolio governance, and resource allocation.

Customer Jobs & Pain Map

Framework / Model: The Experience Strategy Framework

Four-Layer Strategy Model

Layer 1: Segments & Outcomes (Who & Why)

Define target segments and outcomes they need.

Segmentation Dimensions (B2B IT):

• Company Size: SMB (<200 employees), Mid-Market (200–2000), Enterprise (2000+).
• Industry: Financial Services, Healthcare, Manufacturing, Retail, SaaS, etc.
• Use Case: Field operations, data analytics, developer tools, collaboration, etc.
• Maturity: Early adopters (new to category), switchers (replacing competitor), power users (deep usage).

Outcome Mapping (Per Segment):

• SMB Outcome: "Get started in <1 day, self-serve, low cost."
• Enterprise Outcome: "Integrate with existing stack, comply with security/legal, scale to 10K+ users."
• Field Ops Outcome: "Complete tasks offline, on mobile, with low training."

Example (Analytics Platform):

• Segment 1: SMB Marketing Teams → Outcome: "Generate campaign reports in <10 min, no data science skills."
• Segment 2: Enterprise Data Teams → Outcome: "Build custom models, integrate with data warehouse, govern at scale."

Layer 2: Experience Themes (Strategic Bets)

Define 3–5 strategic themes that span 1–3 years.

Themes = Strategic Directions (Not Features).

• Example Themes:
  1. "Mobile-first for field operations" (enable offline, rugged mobile UX, GPS integration).
  2. "AI-assisted analytics" (copilots, auto-insights, natural language queries).
  3. "Enterprise-grade governance" (RBAC, audit trails, compliance automation).
  4. "Developer platform" (APIs, SDKs, extensibility, marketplace).
  5. "Self-serve SMB" (onboarding <1 hour, freemium, no sales touch).

Theme Criteria:

• Outcome-Driven: Solves customer jobs, not internal tech interests.
• Differentiated: Creates competitive advantage.
• Multi-Quarter: Requires sustained investment (not one-off feature).
• Measurable: Has clear success metrics (adoption, revenue, NPS).

Theme Prioritization (Example Framework):

• Impact: Market size (TAM), customer demand (# requests, ARR), competitive pressure.
• Fit: Aligns with company strengths, existing platform, strategic direction.
• Effort: Engineering cost, time-to-market, risk.
• Score: Impact × Fit / Effort. Rank themes. Pick top 3–5.

Layer 3: Portfolio Architecture (How Products Fit Together)

Define how products, modules, and channels work together.

Architecture Patterns:

A. Core + Add-Ons (Modular)

• Core platform (base functionality, most customers).
• Add-ons (advanced features, subset of customers).
• Example: Analytics platform (core) + Advanced ML (add-on) + API Access (add-on).

B. Suite (Integrated Multi-Product)

• Multiple products sold together, tightly integrated.
• Example: Marketing Suite = Email + CRM + Analytics + Ads.

C. Platform + Ecosystem (Extensible)

• Core platform + APIs + third-party integrations/marketplace.
• Example: CRM platform + API + App Marketplace (50+ integrations).

D. Multi-Segment (Tailored Offerings)

• Same core, different packaging/features per segment.
• Example: SMB Edition (self-serve, limited features) vs Enterprise Edition (white-glove, full features).

Portfolio Governance:

• Avoid: Feature bloat (add everything), fragmentation (products don't integrate), cannibalization (products compete).
• Ensure: Clear product boundaries, shared platform/design system, cross-product journeys (e.g., mobile → web continuity).

Layer 4: Investment Allocation (Resources & Budget)

Allocate resources (budget, headcount, time) to themes, segments, and products.

Allocation Framework (Example):

• 70% Sustaining: Core product maintenance, bug fixes, performance, tech debt.
• 20% Growth: Strategic themes (mobile-first, AI, enterprise governance).
• 10% Innovation: Experiments, R&D, new markets (fail-fast, learn).

Allocation by Segment (Example):

• Enterprise (60% of ARR): 50% of resources (maintain + grow).
• SMB (30% of ARR): 30% of resources (self-serve, scale).
• New Segment (10% future ARR): 20% of resources (invest to grow).

Governance:

• Quarterly review: Are allocations driving outcomes (revenue, retention, NPS)?
• Adjust: Shift resources from low-ROI to high-ROI themes/segments.

Diagram description: Visualize as pyramid: Base = Portfolio Architecture (products, modules, channels). Layer 2 = Segments (SMB, Mid-Market, Enterprise). Layer 3 = Experience Themes (strategic bets). Top = Outcomes (customer + business). Strategy flows top-down (outcomes → themes → portfolio → execution).

Implementation Playbook

0–30 Days: Strategy Foundation

Week 1: Segment & Outcome Analysis

• Audit current customer base: Segment by size, industry, use case, maturity.
• For each segment, document: ARR, count, retention, NPS, top jobs (JTBD, Chapter 2).
• Define desired outcomes per segment (use VoC data, Chapter 10; interviews, Chapter 8).
• Example Output: "Enterprise Financial Services (15% of ARR, $3M) → Outcome: Comply with SOC2, integrate with data warehouse, scale to 5K users."

Week 2: Portfolio & Theme Assessment

• Audit current portfolio: Products, modules, features, channels.
• Map portfolio to segments: Which segments does each product serve? Gaps?
• List potential themes (brainstorm with PM, Design, Eng, CS, Sales): Mobile-first, AI, governance, developer platform, self-serve, etc.
• Prioritize themes using Impact × Fit / Effort. Select top 3–5.

Week 3: Define Strategy (Draft)

• Write 1-page strategy doc:
  • Vision: Where we're going (1–3 years). Example: "Be the leading mobile-first analytics platform for field operations."
  • Segments: Top 3 segments, outcomes per segment.
  • Themes: Top 3–5 strategic themes, rationale (why, impact, timeline).
  • Portfolio: How products/modules fit (core + add-ons, multi-segment, etc.).
  • Investment: Allocation (70% sustain, 20% growth, 10% innovation).
• Socialize with leadership (CPO, CEO, Eng Lead, Design Lead). Iterate based on feedback.

Week 4: Align on OKRs

• Map strategy themes to OKRs (Objectives & Key Results).
• Example OKR:
  • Objective: "Lead in mobile-first field operations."
  • Key Results: KR1: Mobile adoption 60% of field users (vs 30% today). KR2: Offline task success rate >95%. KR3: Mobile NPS >50.
• Ensure OKRs measurable, outcome-focused (not output).
• Publish strategy + OKRs (all-hands, Confluence, internal site).

Artifacts: Segment-outcome map, portfolio audit, theme prioritization, 1-page strategy doc, strategic OKRs.

30–90 Days: Operationalize & Govern

Month 2: Roadmap Alignment

• Review roadmap (backlog, planned features). Map each initiative to strategy theme or segment.
• Flag misalignment: Initiatives not tied to theme/segment → Defer or kill.
• Example: Feature request "Excel macros export" doesn't fit any theme → Defer (unless critical for key account).
• Ensure roadmap coverage: Each theme has ≥2 initiatives per quarter.

Month 2–3: Cross-Functional Alignment

• Design: Align design system to themes (e.g., mobile-first theme → mobile components prioritized).
• Engineering: Platform investments to support themes (e.g., offline-first theme → local storage, sync architecture).
• CS: Adoption playbooks per theme (e.g., AI theme → AI feature onboarding, use-case training).
• Sales/Marketing: Messaging per segment-theme (e.g., Enterprise + Governance theme → "SOC2-ready, audit trails, RBAC").

Month 3: Establish Governance Cadence

• Monthly: Theme leads (PM, Design, Eng) review progress (metrics, blockers, adjustments).
• Quarterly: Strategy review (leadership + cross-functional). Assess: OKRs on track? Themes delivering? Adjust allocations.
• Annually: Full strategy refresh (segments, themes, portfolio). Market changes, customer feedback, competitive landscape.

Checkpoints: Roadmap aligned to strategy (≥80% of initiatives tie to themes/segments), cross-functional alignment complete, governance cadence established, first quarterly review held.

Design & Engineering Guidance

Design Patterns for Strategy Execution

Theme-Based Design System Priorities

• If theme = "Mobile-first," prioritize mobile components (touch targets, responsive, offline states).
• If theme = "Enterprise governance," prioritize admin components (RBAC, audit logs, compliance exports).
• Design system roadmap tied to strategic themes (not ad-hoc requests).

Cross-Product Design Consistency

• For portfolios (multi-product, core + add-ons), ensure UX consistency: Navigation, terminology, visual language.
• Use shared design system (tokens, components) across products.
• Conduct cross-product design reviews (monthly): Spot inconsistencies, align on patterns.

Segment-Specific UX

• SMB: Simplicity, self-serve, minimal training. Progressive disclosure, smart defaults.
• Enterprise: Power, flexibility, governance. Advanced settings, bulk actions, audit trails.
• Avoid: One-size-fits-all (frustrates both segments). Solution: Adaptive UI or separate editions (SMB vs Enterprise).

Engineering Patterns for Strategy Execution

Platform Strategy (Theme: "Developer Platform")

• API-first architecture: All features exposed via API (internal + external).
• SDK strategy: Provide SDKs (3+ languages: Python, JavaScript, Go).
• Marketplace: Third-party integrations, app store.
• Governance: API versioning, rate limits, developer docs, sandbox.

Offline-First Architecture (Theme: "Mobile-First Field Ops")

• Local storage (IndexedDB, SQLite on mobile).
• Sync engine (CRDT or operational transform for conflict resolution).
• Service workers (PWA for offline web).
• Visual sync status (synced, syncing, conflict, failed).

AI Infrastructure (Theme: "AI-Assisted Analytics")

• ML pipeline (data → model training → inference → feedback loop).
• Feature store (reusable features for models).
• A/B testing for AI (measure AI-assisted vs manual workflows).
• Human-in-the-loop (AI suggests, user confirms for high-stakes actions).

Multi-Tenant Architecture (Theme: "Enterprise Governance")

• Tenant isolation (data, compute, network).
• RBAC (role-based access control) framework.
• Audit logging (all actions logged: who, what, when, result).
• Compliance automation (SOC2, GDPR, HIPAA controls built-in).

Accessibility, Security, Privacy Across Themes

• Accessibility: All themes must meet WCAG 2.1 AA (Chapter 13). Mobile-first theme: Mobile accessibility (large tap targets, voice input). AI theme: AI outputs accessible (screen reader-friendly).
• Security: Enterprise theme: Security-first (MFA, least privilege, encryption, audit trails). Developer theme: Secure APIs (OAuth, rate limits, DDoS protection).
• Privacy: All themes: Privacy by design (data minimization, consent, export/delete). AI theme: Explainable AI (show why AI recommended X), no PII in training data.

Back-Office & Ops Integration

CS Strategy Alignment

Segment-Based CS Motions

• SMB: Low-touch CS (automated onboarding, self-serve help, chatbot support). CS:ARR ratio 1:$2M.
• Mid-Market: Hybrid CS (onboarding call, quarterly check-ins, playbooks). CS:ARR ratio 1:$1M.
• Enterprise: High-touch CS (dedicated CSM, monthly QBRs, custom success plans). CS:ARR ratio 1:$500K.

Theme-Based Adoption Playbooks

• For each theme, CS builds adoption playbook.
• Example: "AI-Assisted Analytics" theme → CS playbook: (1) Onboarding: Show AI copilot in first session. (2) Adoption: Weekly tips on AI features. (3) Expansion: Identify power users for AI upsell.

Sales/Marketing Strategy Alignment

Segment-Outcome Messaging

• SMB: "Get started in 1 day, no training needed, $49/month."
• Enterprise: "Integrate with your data warehouse, SOC2-compliant, scale to 10K users, white-glove onboarding."
• Sales enablement: Segment-specific pitch decks, case studies, ROI calculators.

Theme-Based Campaigns

• Launch marketing campaigns per theme.
• Example: "Mobile-First Field Ops" theme → Campaign: "Work Anywhere" (mobile app, offline, field case studies).

Competitive Positioning by Theme

• Identify theme where you differentiate vs competitors.
• Example: "Enterprise Governance" theme → Position as "Most secure analytics platform (SOC2, HIPAA, on-prem option)." vs competitors (cloud-only, weaker compliance).

Product Ops Strategy Alignment

Telemetry Strategy per Theme

• Instrument events per theme to measure success.
• Example: "Mobile-First" theme → Events: mobile_app_install, offline_task_completed, sync_duration.
• Dashboard per theme: Mobile adoption %, offline task success, sync reliability.

Experimentation Roadmap per Theme

• Allocate experiment capacity per theme (e.g., 10% of eng capacity for AI theme experiments).
• Example: "AI-Assisted" theme → Experiments: AI vs manual report building (time, accuracy, adoption).

Metrics That Matter

Instrumentation:

• Tag roadmap items with strategy theme + segment (Jira/Linear custom fields).
• Tag product events with theme (e.g., event: ai_copilot_used, theme: "AI-Assisted").
• Segment analytics and revenue by customer segment (SMB, Mid-Market, Enterprise).
• Quarterly OKR reviews: Measure progress, adjust allocations.

AI Considerations

Where AI Helps

Strategy Data Analysis

• AI analyzes customer data (usage, feedback, churn) to surface insights for strategy.
• Example: "High churn in SMB segment (45%) correlates with lack of mobile app usage. Recommend: Mobile-first theme for SMB."

Theme Impact Prediction

• AI models predict theme impact (revenue, retention, adoption) before investment.
• Example: "Mobile-first theme estimated to increase field user retention by 25% (confidence: 70%)."

Portfolio Optimization

• AI recommends portfolio mix (which products/segments to invest in) based on market trends, customer data.
• Example: "Healthcare segment growing 40% YoY, low competition. Recommend: Healthcare-specific features (HIPAA, PHI handling)."

Guardrails

Strategy as Human Judgment, AI as Input

• AI provides data, recommendations. Leadership decides strategy (values, vision, risk tolerance).
• Don't outsource strategy to AI (strategic direction is human, not algorithmic).

Bias in Data

• AI trained on historical data may reinforce existing biases (e.g., over-invest in current segments, under-invest in emerging).
• Avoid: Balance AI recommendations with market research, forward-looking insights, experimentation.

Transparency in Recommendations

• If AI recommends strategy (e.g., "Invest in theme X"), show reasoning (data, assumptions, confidence).
• Leadership reviews, debates, decides (AI doesn't auto-execute strategy).

Risk & Anti-Patterns

Top 5 Pitfalls

1. No Strategy, Just Roadmap (Feature Factory)

   • Team ships features without strategic direction. Roadmap = customer requests + HiPPO. No coherent story, fragmented product.
   • Avoid: Strategy first (segments, outcomes, themes), then roadmap. Strategy drives what to build (and what not to build).

2. Too Many Themes (Strategic Diffusion)

   • Define 10+ themes. Resources spread thin. Nothing gets done well. No differentiation.
   • Avoid: Limit to 3–5 themes (1–3 year horizon). Focus. Say "no" to non-strategic work.

3. Strategy Theater (Beautiful Decks, No Execution)

   • Create gorgeous strategy deck, present at all-hands, then ignore. Roadmap unchanged, OKRs unrelated.
   • Avoid: Operationalize strategy (roadmap alignment, OKRs, governance cadence). Measure progress quarterly.

4. Strategy Disconnect from Customer Reality

   • Strategy based on internal assumptions, competitive analysis, market reports—not customer research.
   • Avoid: Ground strategy in customer data (JTBD, VoC, usability tests, analytics). Validate themes with customers.

5. Static Strategy (Never Updated)

   • Create strategy in 2020, market shifts (new competitors, customer needs change), strategy stale.
   • Avoid: Annual strategy refresh. Quarterly reviews (adjust themes, allocations). Market/customer feedback loops.

Case Snapshot

Company: B2B SaaS (project management platform) Challenge: Fragmented product (15 loosely-related features), unclear positioning, low retention (70%), slow growth. Roadmap = feature requests. No strategic direction. Board pressure: "What's the strategy?"

Experience Strategy Intervention:

• Segment Analysis (Month 1): Analyzed customer base. Found 3 segments: (1) SMB Marketing Teams (40% ARR, low retention 65%), (2) Enterprise IT/Ops (45% ARR, high retention 88%), (3) Software Dev Teams (15% ARR, growing 50% YoY).
• Outcome Mapping: SMB → "Collaborate on campaigns in <1 day, no training." Enterprise → "Manage complex programs, integrate with Jira/Slack, governance." Dev Teams → "Track sprints, integrate with GitHub, automate workflows."
• Theme Prioritization: Brainstormed 12 themes. Prioritized using Impact × Fit / Effort. Selected top 3:
  1. "Enterprise Governance" (Target: Enterprise segment. Impact: High retention, expansion. Fit: Existing strengths. Effort: Medium.)
  2. "Developer Platform" (Target: Dev Teams segment. Impact: High growth, new market. Fit: API exists, needs investment. Effort: High.)
  3. "Mobile-First Collaboration" (Target: SMB + Field Users. Impact: SMB retention lift, new use cases. Fit: No mobile app today, green field. Effort: High.)
• Portfolio Redesign: Core PM platform + 3 add-ons (Enterprise Governance Pack, Developer API/Integrations, Mobile App).
• Investment Allocation: 50% Enterprise theme (high ARR, retention), 30% Developer theme (growth), 20% Mobile theme (SMB retention + new market).
• OKRs: Enterprise theme KR: "Admin adoption of audit logs 70%, Enterprise NPS +10." Developer theme KR: "API usage 3x, 20 marketplace integrations." Mobile theme KR: "Mobile DAU 10K, offline task success 90%."

12-Month Results:

• Retention: Overall: 70% → 84%. Enterprise: 88% → 94% (governance theme). SMB: 65% → 75% (mobile theme).
• Growth: ARR growth: 15% → 35% YoY. Dev segment: 15% → 28% of ARR (developer platform theme).
• NPS: +18 points overall. Enterprise: +12 (governance). Dev Teams: +25 (API/integrations).
• Expansion: Enterprise accounts: 12% → 31% expansion rate (upsell to Governance Pack).
• Clarity: Board/investors: "Finally, a clear strategy." Fundraise: $20M Series B (strategy + execution de-risked investment).
• Team Alignment: Roadmap clarity: 85% of initiatives tied to themes (vs 30% pre-strategy). Teams empowered to say "no" (not in strategy).

Checklist & Templates

Experience Strategy Checklist

• Segment customer base (size, industry, use case, maturity). Analyze: ARR, count, retention, NPS per segment.
• Define outcomes per segment (use JTBD, VoC, interviews). Map: Segment → Desired Outcome.
• Audit portfolio (products, modules, features, channels). Map: Portfolio → Segments served.
• Identify gaps (segments underserved, outcomes not met).
• Brainstorm strategic themes (8–12 ideas). Examples: Mobile-first, AI, governance, developer platform, self-serve.
• Prioritize themes (Impact × Fit / Effort). Select top 3–5.
• Define portfolio architecture (core + add-ons, suite, platform, multi-segment). Ensure: Clear boundaries, integration strategy, shared platform.
• Allocate investment (70% sustain, 20% growth themes, 10% innovation). Allocate by segment based on ARR + strategic importance.
• Write 1-page strategy doc (vision, segments, themes, portfolio, investment).
• Socialize with leadership (CPO, CEO, Eng, Design). Iterate based on feedback.
• Define strategic OKRs (per theme, measurable, outcome-focused).
• Align roadmap to strategy (map initiatives to themes/segments, defer non-strategic work).
• Cross-functional alignment (Design, Eng, CS, Sales/Marketing to themes).
• Establish governance cadence (monthly theme reviews, quarterly strategy reviews, annual refresh).
• Publish strategy (all-hands, Confluence, internal site). Make accessible to all teams.
• Track metrics (segment outcomes, theme success, portfolio health, OKR progress).
• Quarterly strategy review (OKRs on track? Themes delivering? Adjust allocations).
• Annual strategy refresh (market changes, customer feedback, competitive landscape).

Templates

• Segment-Outcome Map Template: [Link to Appendix B]
• Theme Prioritization Matrix (Impact × Fit / Effort): [Link to Appendix B]
• 1-Page Strategy Doc Template: [Link to Appendix B]
• Strategic OKR Template: [Link to Appendix B]
• Portfolio Architecture Diagram: [Link to Appendix B]
• Investment Allocation Model: [Link to Appendix B]

Call to Action (Next Week)

3 Actions for the Next Five Working Days:

1. Segment Your Customer Base (Day 1–2): Pull CRM data. Segment by: Company size (SMB, Mid-Market, Enterprise), Industry (top 3–5), Use case (if applicable). For each segment, calculate: ARR, customer count, retention rate, NPS (if available). Identify: Top 3 segments by ARR + strategic importance (growth, retention).

2. Define Outcomes per Segment (Day 3–4): For top 3 segments, define desired outcomes. Use existing data: JTBD (Chapter 2), VoC (Chapter 10), interviews (Chapter 8). Format: "Segment X wants to [outcome]." Example: "SMB Marketing Teams want to collaborate on campaigns in <1 day, no training." Validate: Interview 3–5 customers per segment. Ask: "What outcome would make this product indispensable?"

3. Draft 3 Strategic Themes (Day 5): Brainstorm 5–8 potential themes (mobile-first, AI, governance, developer platform, self-serve, etc.). Prioritize using simple scoring: Impact (1–10), Fit with strengths (1–10), Effort (Low/Med/High → 10/5/1). Calculate: Impact × Fit / Effort. Pick top 3. Write 1-sentence description per theme. Example: "Mobile-First Field Ops: Enable offline task completion on mobile for field users (target: 60% mobile adoption, offline task success >95%)." Share with PM, Design, Eng leads. Discuss: Do these themes resonate? Missing anything?

Next Chapter: Chapter 15 — Outcome-Driven Roadmapping