Head of Legacy Engineering – Migration Enablement

Turnkey Africa Ltd

. Lead Caava’s legacy engineering portfolio, protecting the company’s largest current revenue source .

Posted 9/18/2026full-timeNairobi • KenyaLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading engineering portfolios, managing complex delivery and modernization projects, and ensuring the reliability of legacy systems. Proficient in Oracle, PL/SQL, ADF, WebLogic, and Java, with a strong focus on customer satisfaction and risk management.

Highest-signal resume keywords

Engineering LeadershipOracle ExpertiseData Migration ExperienceCommercial JudgementRegulated Industry Experience

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

OraclePL/SQLADFWebLogicJavaData MigrationApplication SupportIncident ImprovementTechnical Debt ManagementControlled Upgrades

Soft Skills

Collaborative LeadershipCalm Under PressureTransparent CommunicationPragmatic Decision-MakingInvestment in People Development

Industry Keywords

InsuranceFinancial ServicesRegulated IndustryEnterprise TechnologyCustomer SOWs

Tech Stack

Tools & technologies

JavaOracleSQL

About the role

Key responsibilities & impact

Lead Caava’s legacy engineering portfolio, protecting the company’s largest current revenue source
Support new customer work, necessary modernisation and progressive migration to Evolve
Balance Run, Grow & Modernise, and Migrate priorities through domain leads and specialist teams
Keep legacy products reliable and customers supported through application support, incident improvement and safe change
Maintain engineering coverage and recovery readiness with Platform Operations
Match commitments to available skills and protect support and migration capacity
Close capacity gaps through hiring, partners and cross-training
Retain critical knowledge, strengthen succession and career paths, and develop teams
Own engineering delivery of legacy SOWs, projects and lifecycle upgrades, including WebLogic, Java and Oracle
Align estimates, resourcing, change control, testing and customer acceptance to meet commitments and protect delivery margin
Reduce security, supportability and technical-debt risks through modernisation
Own the integrated customer migration plan and legacy-side readiness, including business-rule discovery, data conversion, reconciliation and retirement
Coordinate dependencies, rehearsals, cutover and rollback readiness
Build reusable upgrade and migration patterns
Retire services, licences and capacity after customer acceptance, data integrity, operational readiness and commercial exit conditions are met
Own the roadmap, budget, risks and quarterly outcomes
Provide the CTO and ExCo with evidence on delivery, capacity and revenue exposure
Escalate trade-offs early with recommendations and challenge unsafe, underfunded or under-resourced commitments
Establish a baseline of customers, revenue, commitments, capacity and lifecycle risks
Agree a resourced Run, Grow & Modernise, and Migrate roadmap
Put intake controls and priority staffing actions in motion
Demonstrate control of capacity and forecasts, deliver milestones and migration rehearsals or customer proof points, and present quarterly portfolio reviews

Requirements

What you’ll need

5+ years in engineering or enterprise technology
2+ years leading teams or complex delivery, support or modernisation portfolios
Experience protecting revenue-critical production services while delivering customer SOWs and managing constrained specialist capacity
Technical credibility in Oracle, PL/SQL, ADF, WebLogic, Java and integrations
Practical experience in controlled upgrades and data migration
Strong commercial judgement across estimation, scope, costs and acceptance
Ability to communicate evidence, trade-offs and recommendations at executive level
Calm, pragmatic and collaborative leadership style
Transparency about risk and discipline about commitments
Investment in developing people
Insurance, financial services or other regulated-industry experience strongly preferred

Benefits

Comp & perks

Revenue-critical portfolio ownership
Career paths and team development opportunities
Hiring, partner capacity and cross-training opportunities
Succession planning and knowledge-retention support