CDO & Digital Office - 30/60/90 Day Plan¶
Prepared by: Daniel O'Reilly, Chief Digital Officer
Prepared for: Yassir Pasha, Chief Executive Officer / Executive Leadership Team
Date: 7 April 2026
Classification: Confidential - ELT Only
Version: 2.0 (supersedes CDO 90-Day Plan v1.0, dated 3 April 2026)
How to Read This Document¶
This plan has two parts:
-
Part A: CDO 30/60/90 - the CDO's personal accountability across the entire division (Solution Engineering, Platform Engineering, Data Engineering, Production Engineering, Information Security, Product Management, Digital Office). Updated to reflect Week 1 progress.
-
Part B: Digital Office 30/60/90 - the dedicated plan for the new Digital Office team, the CDO's strategic execution arm.
Each initiative includes: priority (P1–P4), owner, deadline, key results, pros/cons, estimated cost/value, and a status tracker.
Priority definitions: - P1 - Regulatory/Licence Critical: Delays the DFSA Cat 3D licence or creates regulatory risk - P2 - Revenue/Expansion Critical: Blocks Saudi Arabia entry or corridor revenue - P3 - Operational Excellence: Improves reliability, security, or efficiency - P4 - Strategic Foundation: Builds long-term capability
Part A: CDO 30/60/90 Day Plan¶
Progress Update - Week 1 (Days 1–8)¶
| Initiative | Status | Notes |
|---|---|---|
| 1.1 Operating Model v1.0 | ✅ Substantially complete | 17 sections written (1.1 MB). Pushed to Bitbucket (simpaisa1/opmodel). Board presentation pending. |
| CDO Division Org Chart | ✅ v4.0 complete | 7 tribes defined. 63 placed, 13 hires, 1 pool, 1 resigned. Target: 70. |
| Ways of Work Framework | ✅ 14 documents drafted | W-01 through W-50 published to Confluence. Operating rhythms, engineering, security, data, product, ops, compliance, HR. |
| Confluence Architecture Space | ✅ Created | Standards, regulatory playbooks, threat models, workflow diagrams all published. |
| Regulatory Playbooks | ✅ 5 markets drafted | Pakistan, Bangladesh, Nepal, UAE, Saudi Arabia, Egypt. |
| Threat Models | ✅ 3 completed | Pay-Outs, Merchant Portal, Remittances. |
Assessment: Week 1 output is exceptional. The documentation foundation is built. The risk is now execution - moving from documents to delivered change.
Phase 1: Assess and Document (Days 1–30)¶
Period: 30 March – 29 April 2026
1.1 Operating Model Completion ✅ IN PROGRESS¶
| Field | Value |
|---|---|
| Priority | P1 |
| Owner | CDO |
| Deadline | 9 April (finalisation) / 29 April (board presentation) |
| Status | 80% complete - content written, board deck pending |
Key Results: - [x] All 17 sections drafted and version-controlled - [x] Pushed to Bitbucket (simpaisa1/opmodel, DIG project) - [ ] CEO review and sign-off - [ ] Board presentation prepared and delivered
Pros: Establishes CDO credibility with the board on Day 30. Becomes the onboarding baseline for all future hires.
Cons: Time-intensive to finalise while other Phase 1 assessments run in parallel.
Value: Non-quantifiable but foundational - every subsequent initiative references this document.
1.2 Technology Assessment¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CTO (Saqlain Raza) |
| Deadline | 24 April 2026 |
| Status | Not started - dependent on CTO bandwidth |
Key Results: - [ ] AWS account inventory (all accounts, services, spend by service line) - [ ] Data residency compliance assessed per market (PK, BD, NP, IQ, AE) - [ ] Cloudflare migration candidates identified - [ ] Monthly AWS spend confirmed - [ ] Single-region exposure flagged as risk
Pros: Provides the factual basis for Cloudflare migration and cost optimisation.
Cons: Requires DevOps team time; may reveal uncomfortable truths about infrastructure debt.
Cost: Internal effort only (~40 engineer-hours).
Value: Enables USD 200K+ annualised savings target (Phase 3).
1.3 Security Posture Review¶
| Field | Value |
|---|---|
| Priority | P1 |
| Owner | CISO (Danish Hamid) |
| Deadline | 27 April 2026 |
| Status | Threat models for 3 services completed. Full posture review pending. |
Key Results: - [x] Threat models: Pay-Outs, Merchant Portal, Remittances - [ ] ISO 27001 scope confirmed for group structure (9 entities) - [ ] PCI DSS CDE boundaries documented - [ ] Pen test history reviewed (last test, critical findings, remediation status) - [ ] Gaps risk-rated (Critical/High/Medium/Low)
Pros: DFSA submission requires evidence of security posture. Early completion accelerates licence.
Cons: May reveal gaps that require immediate investment.
Value: Direct enabler for DFSA Cat 3D licence (revenue impact: entire UAE operations).
Industry context: 45% of financial organisations experienced AI-powered cyberattacks in 2025. Financial services is the most targeted industry. A single breach averages USD 5.9M in financial services. Proactive investment costs 10–20x less than breach remediation.
1.4 Product Audit¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CPO (Rizwan Zafar) |
| Deadline | 27 April 2026 |
| Status | Not started |
Key Results: - [ ] Revenue and volume by product line and corridor documented - [ ] Product-market fit rated per corridor (Strong/Developing/Weak/Exit) - [ ] Roadmap reviewed against CDO strategic priorities - [ ] 3–5 product recommendations for Phase 2
Pros: Ensures capital is directed at highest-return corridors.
Cons: May create tension if CPO's roadmap diverges from CDO priorities.
Value: Revenue optimisation across 7 markets. Saudi corridor sizing.
1.5 Team Assessment¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO |
| Deadline | 24 April (1:1s) / 29 April (gap analysis) |
| Status | Org chart v4.0 complete. 1:1s in progress. |
Key Results: - [x] Org restructure designed (7 tribes, target 70) - [x] Role mappings defined for all 65 current staff - [ ] 1:1s completed with CPO, CISO, CTO and their directs - [ ] Capability gap analysis documented - [ ] Retention risks identified - [ ] CTO appointment preliminary view formed
Pros: Restructure already designed - execution is the remaining work.
Cons: Reapplication process will create anxiety. Must be handled with care.
Impact: 21 redeployments, 13 new hires, 1 resignation. Cultural reset.
1.6 Vendor Audit¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CTO + Finance |
| Deadline | 27 April 2026 |
| Status | Not started |
Key Results: - [ ] All vendors catalogued with annual spend - [ ] Contract end dates and auto-renewal clauses documented - [ ] Lock-in risk rated (High/Medium/Low) - [ ] Renegotiation or termination candidates flagged
Pros: Quick wins on cost - typically 15–30% savings found on first audit.
Cons: Requires Finance cooperation and contract access.
Value: Estimated USD 50K–150K in immediate savings opportunities (Datadog alone estimated at USD 150K–200K/year).
1.7 DFSA Cat 3D Gap Remediation¶
| Field | Value |
|---|---|
| Priority | P1 |
| Owner | CDO + CISO |
| Deadline | 19 April 2026 |
| Status | Gap analysis exists. Remediation tracking not yet started. |
Key Results: - [ ] All CDO-domain gaps reviewed and triaged - [ ] Each gap has named owner, remediation action, target date - [ ] No CDO-domain item on critical path without committed date - [ ] CISO confirms tech/security evidence pack is submission-ready
Pros: Directly unblocks the DFSA licence - the single most important regulatory milestone.
Cons: Compressed timeline (12 days remaining).
Value: DFSA licence enables UAE operations - estimated revenue impact USD 2M+ in Year 1.
Industry context: DFSA is becoming more demanding. AI governance frameworks and operational resilience are emerging requirements. Proactive investment now avoids costly remediation and accelerates approval.
1.8 Quick Wins¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CDO |
| Deadline | 14 April (identify) / 29 April (deliver) |
| Status | Week 1 already delivered several visible outputs |
Quick Wins Delivered (Week 1): 1. ✅ Operating Model v1.0 - most comprehensive group document ever produced 2. ✅ CDO Division Org Chart v4.0 - complete restructure with transition plan 3. ✅ 14 Ways of Work documents - governance framework from scratch 4. ✅ Bitbucket repo for OpModel - version control for governance docs 5. ✅ Confluence architecture space - standards, playbooks, threat models
Quick Wins Remaining (Week 2–4): 6. [ ] Terminate or renegotiate one over-priced vendor contract 7. [ ] Close one high-severity security finding 8. [ ] Establish first public-facing SLA commitment
1.9 Board Presentation: Operating Model v1.0¶
| Field | Value |
|---|---|
| Priority | P1 |
| Owner | CDO |
| Deadline | 29 April 2026 |
| Status | Content ready. Deck not yet built. |
Key Results: - [ ] Board deck prepared (30–45 minutes + Q&A) - [ ] CEO pre-briefed - [ ] Board endorses operating model - [ ] Board approves Phase 2 investment outline
Pros: Establishes CDO as a board-level strategic voice from Day 30.
Cons: Board may challenge investment requests without financial modelling.
Value: Unlocks H2 2026 budget for Cloudflare, SRE, Data Engineering, Saudi expansion.
Phase 2: Restructure and Implement (Days 31–60)¶
Period: 30 April – 28 May 2026
2.1 Org Restructure Execution¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO + HR |
| Deadline | 28 May 2026 |
| Status | Designed. Not yet communicated. |
Key Results: - [ ] Restructure communicated to all 65 staff - [ ] Reapplication process launched for changed roles - [ ] 13 new hire JDs published and recruitment initiated - [ ] Digital Office team operational (Arsalan, Wajih, Ahsan, Annus in new roles) - [ ] Head of Data Engineering search launched
Tribes established:
| Tribe | Head | Headcount (Current → Target) |
|---|---|---|
| Solution Engineering | CTO | 27 → 27 |
| Platform Engineering | Muhammad Mohsin | 9 → 9 |
| Data Engineering | Head of Data (hire) | 2 → 6 |
| Production Engineering | Muhammad Owais Khalid | 14 → 14 |
| Information Security | Danish Hamid (CISO) | 9 → 9 |
| Product Management | Rizwan Zafar (CPO) | 8 → 8 |
| Digital Office | CDO | 4 → 9 |
Pros: Clear accountability. Modern engineering organisation. AI-native model.
Cons: Reapplication process will cause anxiety and potential attrition.
Impact: Expected natural attrition brings 77 (current + hires) down to target 70.
Cost: Recruitment costs for 13 hires estimated at USD 50K–80K (mix of direct and agency).
2.2 Cloudflare Migration: Phase 1 POC¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CTO |
| Deadline | 27 May 2026 |
| Status | Dependent on 1.2 (Technology Assessment) |
Key Results: - [ ] Cloudflare enterprise account provisioned - [ ] One corridor POC deployed (Pakistan recommended) - [ ] Latency benchmarked: Cloudflare vs. AWS baseline - [ ] In-country data routing validated - [ ] Go/no-go recommendation presented
Pros: 40–60% reduction in per-transaction costs. Active-active DR capability. Edge routing for MENA expansion.
Cons: Engineering effort during restructure period. Risk of Workers limitations for complex payment logic.
Cost: USD 15K–25K (Cloudflare enterprise + engineering time).
Value: Enables USD 200K+ annual infrastructure savings at scale.
2.3 SRE Foundation¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CTO |
| Deadline | 14 May (SLOs) / 27 May (error budget) |
| Status | Not started |
Key Results: - [ ] SLOs defined for all critical services - [ ] Error budget policy published - [ ] CAB formally deprecated - [ ] On-call rotation established for at least one team
Pros: Reliability becomes measurable and enforceable. Board-level metric.
Cons: Cultural resistance to error budget enforcement. Test coverage may be too low.
Cost: Tooling USD 35K–65K/year (feature flags, PagerDuty). SRE hire USD 80K–120K.
Value: MTTR reduction, deployment frequency increase, customer-visible reliability improvement.
2.4 Daily Deploy Pipeline¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CTO |
| Deadline | 27 May 2026 |
Key Results: - [ ] One team deploying to production daily - [ ] Jenkins pipeline automated (unit tests, integration tests, Snyk scan) - [ ] Feature flags implemented - [ ] Automated rollback within 5 minutes
Pros: Engineering velocity. Faster time-to-market for Saudi corridors.
Cons: Requires test coverage audit first. Risk of increased incidents if coverage is low.
Cost: Internal effort (~60 engineer-hours). Feature flag tooling USD 20K–40K/year.
Value: Industry research shows only 25% of payment firms are modernising. This is competitive advantage.
2.5 OKR Rollout: Technology Teams Pilot¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CDO |
| Deadline | 27 May 2026 |
Key Results: - [ ] OKR framework defined - [ ] Q3 2026 OKRs agreed with CPO, CISO, CTO - [ ] OKRs cascaded to teams - [ ] Review cadence established - [ ] CEO briefed for wider rollout in Q4
Pros: Aligns all 70 people to measurable outcomes. Board-reportable.
Cons: OKR fatigue risk if not implemented with discipline.
Cost: Tooling USD 5K–15K/year. CDO time investment.
Value: Performance visibility. Accountability culture.
2.6 CTO Appointment Decision¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO |
| Deadline | 19 May 2026 |
Key Results: - [ ] CDO recommendation submitted to CEO - [ ] If appointment: scope, compensation, reporting confirmed - [ ] If external hire: JD drafted, search initiated - [ ] No ambiguity in CTO role beyond Day 60
Pros: Removes "Acting" uncertainty. Enables CTO to lead with authority.
Cons: External hire would take 3–6 months and create a leadership gap.
2.7 Product Roadmap Alignment¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO + CPO |
| Deadline | 27 May 2026 |
Key Results: - [ ] H2 2026 unified roadmap published - [ ] Saudi/MENA expansion technology requirements included - [ ] Cloudflare, SRE, active-active DR treated as first-class roadmap items - [ ] CPO and CDO aligned on prioritisation
Industry context: Cross-border payments market growing at 16% CAGR to USD 89B by 2030. ISO 20022 is consolidating as the foundational standard. Real-time payment rails are compressing settlement from days to seconds.
2.8 Security Improvements¶
| Field | Value |
|---|---|
| Priority | P1 |
| Owner | CISO |
| Deadline | 27 May 2026 |
Key Results: - [ ] All Critical findings in active remediation - [ ] 50% of High findings closed - [ ] Fortnightly status report to CDO
Phase 3: Measure and Optimise (Days 61–90)¶
Period: 29 May – 27 June 2026
3.1 KPI Baseline Establishment¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CDO + CTO + CPO |
| Deadline | 24 June 2026 |
Key Results: - [ ] 60 of 83 operating model KPIs have live baseline values - [ ] Data source and measurement method documented per KPI - [ ] KPI dashboard agreed with CEO and board
Value: Transforms the operating model from a document into a live management system.
3.2 Cost Optimisation¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CTO + Finance |
| Deadline | 19 June 2026 |
Key Results: - [ ] USD 200K annualised savings identified - [ ] USD 50K committed or in flight - [ ] AWS reserved instance / savings plan analysis completed - [ ] Datadog cost vs. alternative modelled
Industry context: Grafana Cloud typically 40–60% cheaper than Datadog. Self-hosted ELK saves 30–50% before headcount. Current Datadog estimated at USD 150K–200K/year.
3.3 Data Strategy¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO + Head of Data Engineering (if hired) |
| Deadline | 24 June 2026 |
Key Results: - [ ] Current state documented (MySQL, PostgreSQL, MongoDB, DocumentDB, Redis, Looker, Metabase) - [ ] Target state defined (cloud data warehouse, dbt, self-service BI) - [ ] Build vs. buy recommendation per component - [ ] Implementation roadmap aligned to DT Roadmap
Industry context: Fintech analytics market hitting USD 5.3B in 2026 (25% YoY growth). 81% of fintechs embed analytics as standard. Real-time processing is table stakes. Embedded analytics drive retention and upsell.
3.4 AI and ML Opportunities¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CDO |
| Deadline | 19 June (assessment) / 27 June (first initiative confirmed) |
Key Results: - [ ] 3–5 AI/ML use cases identified, sized for effort and ROI - [ ] Reconciliation automation confirmed as Phase 1 priority - [ ] Phase 1 initiative has named lead, scope, start date - [ ] CEO and CPO briefed on AI/ML roadmap
Industry context: Industry is shifting from generative AI to agentic AI - autonomous systems that execute multi-step tasks. Frontier firms report 3x higher AI ROI. Top deployment: fraud detection (64%), loan processing (61%), customer onboarding (59%). AI automation can reduce operational headcount by 30–40% as you scale to new markets.
3.5 Saudi/MENA Talent Pipeline¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO + HR |
| Deadline | 24 June (plan) / 27 June (recruitment active) |
Key Results: - [ ] Roles defined for Saudi launch - [ ] Location strategy confirmed - [ ] Compensation benchmarks produced - [ ] JDs published, recruiter engaged for at least 2 roles
Industry context: Saudi fintech market reached USD 39.9B in 2024, growing 13.7% CAGR to USD 125B by 2034. 224 licensed fintechs already - the window is open but filling fast. Saudi-South Asia remittance corridors align perfectly with Simpaisa's footprint.
3.6 Board Quarterly Report¶
| Field | Value |
|---|---|
| Priority | P1 |
| Owner | CDO |
| Deadline | 27 June 2026 |
Key Results: - [ ] Strategic progress vs. 90-day plan - [ ] KPI dashboard with actual values - [ ] Cost optimisation delivered and pipeline - [ ] Security posture improvement - [ ] H2 2026 investment requests with business cases
What We Will NOT Do in 90 Days¶
| Out of Scope | Reason |
|---|---|
| Full Cloudflare production migration | POC first - production migration is H2 2026 |
| Data warehouse implementation | Strategy first (Phase 3), build in H2 2026 |
| AI/ML production models | Assessment and first initiative only |
| Central Asia market entry | Saudi Arabia is the priority; Central Asia is 2027 |
| Full observability platform replacement | Assessment and POC only - migration is H2 2026 |
| Complete headcount to 70 | Hiring takes 3–6 months; target is 70 by end of 2026 |
Capital Ladder - Investment Phasing¶
| Quarter | Investment | Purpose | Expected Return |
|---|---|---|---|
| Q2 2026 (now) | USD 50K–80K | Recruitment (13 hires), tooling (feature flags, PagerDuty) | Org restructure, reliability foundation |
| Q3 2026 | USD 100K–150K | Cloudflare enterprise, SRE tooling, observability POC, Head of Data salary | Infrastructure modernisation, cost savings pipeline |
| Q4 2026 | USD 150K–200K | Cloudflare production, observability migration, data warehouse foundation | USD 200K+ annualised savings, real-time analytics |
| H1 2027 | USD 200K–300K | Multi-market Cloudflare rollout, Saudi tech team, AI/ML production | Saudi revenue, cross-corridor intelligence |
Total Year 1 investment: USD 500K–730K
Expected Year 1 return: USD 200K+ cost savings + DFSA licence revenue (USD 2M+) + Saudi corridor revenue (TBD)
Payback: < 12 months on cost savings alone; < 6 months including DFSA revenue
Part B: Digital Office - 30/60/90 Day Plan¶
What is the Digital Office?¶
The Digital Office is the CDO's strategic execution arm. It sits between strategy and delivery - validating opportunities upstream of SDLC, owning delivery methodology, running spikes and PoCs, and managing developer experience. It does NOT do day-to-day engineering or product management. It does the thinking that those teams then execute.
Team (Current):
| Name | Role | Background |
|---|---|---|
| Arsalan Pervez | Manager Digital Delivery | was: PMO Manager |
| Wajih Aslam | Digital Coach | was: Agile Coach |
| Muhammad Ahsan | Associate Delivery Analyst | was: Project Coordinator |
| Annus Ahmed | Associate Delivery Analyst | was: Project Coordinator |
Hires Planned (5):
| Role | Purpose |
|---|---|
| Principal Digital Architect | Solution design, feasibility, technical prototyping, PoC architecture |
| Digital Product Strategist | Market research, concept validation, business case, opportunity sizing |
| Principal Digital Engineer | Developer experience - internal portals, golden paths, CLI tooling |
| Senior Digital Engineer | Rapid PoCs, technical spikes, API exploration, data modelling |
| Senior Digital Engineer | Rapid PoCs, technical spikes, API exploration, data modelling |
Target headcount: 9 (4 current + 5 hires)
Digital Office Mission¶
Validate opportunities upstream of SDLC. Produce validated concepts with architecture blueprints for handoff to Product and Engineering. Kill bad ideas fast. Run spikes and Sprint 0 activities. Own the delivery methodology and developer experience.
Phase 1: Establish and Assess (Days 1–30)¶
Period: 7 April – 6 May 2026
DO-1.1 Team Onboarding and Role Clarity¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO |
| Deadline | 14 April 2026 |
Key Results: - [ ] 1:1s with all 4 team members - explain new roles, expectations, career path - [ ] Digital Office charter document published (mission, scope, what we do / don't do) - [ ] Reporting lines and operating cadence established - [ ] Each team member has a 30-day personal development objective
Pros: Sets the tone. People moving from PMO/coordination roles need clarity on the strategic shift.
Cons: Team members may feel anxious about capability gap (PMO → Digital Office is a stretch).
Mitigation: Pair each person with a mentor from Engineering or Product for the first 30 days.
DO-1.2 Delivery Methodology Ownership¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | Manager Digital Delivery (Arsalan Pervez) |
| Deadline | 21 April 2026 |
Key Results: - [ ] Review all 14 Ways of Work documents and identify gaps or inconsistencies - [ ] Establish the Digital Office as the owner of delivery methodology across the CDO division - [ ] Create a delivery health dashboard (cycle time, WIP, throughput per team) - [ ] Run the first cross-team delivery standup (CDO Division Standup per W-01)
Pros: Arsalan's PMO background is directly relevant - this is a natural extension, not a stretch.
Cons: Risk of becoming a "governance police" rather than enabling function. Must be positioned as service, not oversight.
Value: Visibility into delivery health across 7 tribes. Early warning on blockers.
DO-1.3 Current State Process Audit¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | Digital Coach (Wajih Aslam) |
| Deadline | 28 April 2026 |
Key Results: - [ ] Observe every Kanban team's standup and planning session (at least once each) - [ ] Document: actual vs. prescribed process (W-10) for each team - [ ] Identify top 3 process pain points per team - [ ] Produce a "State of Delivery" report for the CDO
Pros: Wajih's agile coaching background is perfect for this. Builds trust by listening first.
Cons: Teams may see observation as surveillance. Frame as "how can we help you" not "what are you doing wrong."
Value: Evidence-based view of where delivery methodology is working and where it isn't.
DO-1.4 Tool Standards Baseline¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | Associate Delivery Analysts (Ahsan + Annus) |
| Deadline | 28 April 2026 |
Key Results: - [ ] Audit all tools in use across CDO division (Jira, Confluence, Bitbucket, Slack, etc.) - [ ] Map actual usage against W-03 (Tool Standards) - [ ] Identify tool sprawl, unused licences, and consolidation opportunities - [ ] Produce a tool register with cost, owner, and contract status
Pros: Concrete, measurable task. Good onboarding project for associates.
Cons: Low strategic value in isolation - but feeds vendor audit (1.6) and cost optimisation (3.2).
Value: Typically finds 10–20% in unused licence costs.
DO-1.5 Hire: Principal Digital Architect¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO + HR |
| Deadline | JD published by 14 April. Interview pipeline active by 28 April. |
Key Results: - [ ] JD published on LinkedIn, Bitbucket Talent, and regional job boards - [ ] Recruiter engaged (internal or agency) - [ ] First round interviews by end of Phase 1
Rationale: This is the most critical Digital Office hire. The Digital Architect owns solution design, feasibility, and PoC architecture - without this person, the team cannot do its core job.
Phase 2: Build Capability and Prove Value (Days 31–60)¶
Period: 7 May – 5 June 2026
DO-2.1 First Spike: Saudi Arabia Technology Readiness¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | Digital Office (CDO sponsors) |
| Deadline | 21 May 2026 |
Key Results: - [ ] Technology requirements for SAMA licensing documented - [ ] Data residency requirements for Saudi Arabia mapped - [ ] Integration requirements for Saudi payment rails identified (SARIE, mada, STC Pay) - [ ] Architecture blueprint for Saudi corridor produced - [ ] Go/no-go readiness assessment presented to CDO
Pros: Proves the Digital Office model - upstream validation before Engineering builds anything.
Cons: Requires domain expertise the team may not yet have. May need external consultant input.
Value: De-risks the single highest-priority expansion market. Prevents Engineering from building the wrong thing.
Industry context: Saudi fintech market growing 13.7% CAGR to USD 125B by 2034. 70% non-cash transactions already achieved. Window is open but 224 fintechs already licensed.
DO-2.2 Developer Experience Assessment¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | Digital Office |
| Deadline | 28 May 2026 |
Key Results: - [ ] Time-to-first-commit measured for new engineers (current state) - [ ] Developer satisfaction survey conducted across all engineering teams - [ ] Top 5 developer experience pain points identified - [ ] Golden paths defined for common development tasks - [ ] Internal developer portal requirements documented
Pros: Directly improves engineering velocity. Measurable impact.
Cons: Requires the Principal Digital Engineer hire (may not be in place yet).
Mitigation: Start with the assessment; build the solutions when the hire arrives.
Value: Industry research shows developer experience improvements drive 20–40% productivity gains.
DO-2.3 Delivery Methodology Rollout¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | Digital Coach (Wajih Aslam) + Manager Digital Delivery (Arsalan) |
| Deadline | 5 June 2026 |
Key Results: - [ ] 10-day delivery cycle formally adopted by all 4 engineering squads (Pay-Ins, Pay-Outs, Portals, Remittance) - [ ] Kanban boards standardised per W-10 - [ ] WIP limits enforced - [ ] Day 10 retro/demo/groom running consistently - [ ] Delivery metrics being captured (cycle time, throughput, WIP age)
Pros: Transforms paper process (W-10) into actual practice.
Cons: Teams may resist change. "We already do agile" pushback likely.
Mitigation: Frame as "we're helping you do what the document says" not "we're changing how you work."
DO-2.4 Architecture Review Board Operations¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CDO (chairs) + Digital Office (secretariat) |
| Deadline | First ARB by 5 May (per W-01: 1st Tuesday monthly) |
Key Results: - [ ] First ARB meeting held - [ ] ADR template published and adopted - [ ] First 3 ADRs drafted (Cloudflare, observability, data warehouse) - [ ] Standards exception process documented - [ ] ARB cadence running monthly
Pros: Establishes architectural governance without bureaucracy.
Cons: Risk of becoming a bottleneck if not run with pace.
DO-2.5 Continue Hiring¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | CDO + HR |
| Deadline | Ongoing |
Key Results: - [ ] Principal Digital Architect: offer extended or second round in progress - [ ] Digital Product Strategist: JD published, pipeline active - [ ] Principal Digital Engineer: JD published, pipeline active - [ ] Senior Digital Engineers (x2): JDs published
Phase 3: Scale and Embed (Days 61–90)¶
Period: 6 June – 5 July 2026
DO-3.1 Spike: AI-Assisted Reconciliation¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | Digital Office |
| Deadline | 26 June 2026 |
Key Results: - [ ] Current reconciliation process documented (manual effort, error rate, time per market) - [ ] AI reconciliation POC scoped with Data Engineering - [ ] Feasibility assessment: data availability, model approach, expected accuracy - [ ] Business case produced (hours saved × cost per hour × markets) - [ ] Handoff to Data Engineering and Solution Engineering for implementation
Pros: Highest-ROI AI use case identified in CDO 90-Day Plan. Digital Office validates; Engineering builds.
Cons: Requires Data Engineering team to exist (Head of Data may not be hired yet).
Value: Reconciliation is manual across 7 markets. Automation could save 500+ hours/month at scale.
DO-3.2 Spike: ISO 20022 Readiness Assessment¶
| Field | Value |
|---|---|
| Priority | P2 |
| Owner | Digital Office |
| Deadline | 3 July 2026 |
Key Results: - [ ] Current message format compliance assessed per corridor - [ ] ISO 20022 gap analysis produced - [ ] Migration roadmap drafted - [ ] Regulatory deadline per jurisdiction documented
Industry context: ISO 20022 is consolidating as the foundational standard for cross-border payments. Enables richer data for analytics and compliance. Non-compliance will lock Simpaisa out of emerging real-time payment links.
DO-3.3 Delivery Health Report: Month 3¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | Manager Digital Delivery (Arsalan) |
| Deadline | 5 July 2026 |
Key Results: - [ ] Delivery metrics dashboard live (cycle time, throughput, WIP, deployment frequency per team) - [ ] Month-over-month trend analysis - [ ] Recommendations for CDO on capacity allocation - [ ] Input to CDO Board Quarterly Report (3.6)
DO-3.4 Digital Office OKRs for Q3 2026¶
| Field | Value |
|---|---|
| Priority | P3 |
| Owner | CDO |
| Deadline | 5 July 2026 |
Key Results: - [ ] Digital Office Q3 OKRs published (aligned to CDO OKRs) - [ ] Each team member has individual OKRs - [ ] First OKR check-in completed
Suggested Q3 OKRs:
Objective 1: Validate 3 strategic opportunities upstream of SDLC - KR1: Complete Saudi Arabia technology readiness spike with architecture blueprint - KR2: Complete AI reconciliation feasibility spike with business case - KR3: Complete ISO 20022 readiness assessment with migration roadmap
Objective 2: Improve engineering delivery velocity by 20% - KR1: All 4 engineering squads running standardised 10-day cycles with metrics - KR2: Average cycle time reduced by 20% from Phase 1 baseline - KR3: Developer experience score improved by 15% from baseline survey
Objective 3: Hire 3 of 5 planned Digital Office roles - KR1: Principal Digital Architect hired and onboarded - KR2: Digital Product Strategist hired - KR3: At least 1 Senior Digital Engineer hired
Digital Office - What We Will NOT Do¶
| Out of Scope | Why |
|---|---|
| Write production code | That's Solution Engineering's job. We validate and hand off. |
| Own the product backlog | That's Product Management's job. We run spikes that inform the backlog. |
| Manage people in other tribes | We coach and enable, not manage. No dotted-line reporting. |
| Run programme management | We killed the PMO. We don't replace it. We enable self-organising teams. |
| Own compliance or regulatory | That's Information Security and Regulatory Affairs. We support with tech assessments. |
Summary: Digital Office Value Proposition¶
| Month | Deliverables | Business Value |
|---|---|---|
| Month 1 | Team onboarded, delivery methodology owned, process audit, tool audit, first hire in pipeline | Governance foundation, delivery visibility |
| Month 2 | Saudi readiness spike, DX assessment, delivery methodology live, ARB operational | Saudi expansion de-risked, engineering velocity baseline |
| Month 3 | AI reconciliation spike, ISO 20022 assessment, delivery health metrics, Q3 OKRs | Two validated business cases, measurable delivery improvement |
90-day cost: USD 0 incremental (team is redeployed from existing headcount) + USD 30K–50K recruitment costs for first 1–2 hires
90-day value: Saudi expansion de-risked (USD multi-million revenue opportunity), AI reconciliation business case (500+ hours/month savings potential), delivery velocity baseline (enables continuous improvement)
Document version 2.0. Review at Day 30, Day 60, and Day 90. Living document - update as conditions change.