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Head of Legacy Engineering and Migration Enablement at Caava Group
Caava Group
October 8, 2026
Full-time
On-site
Role Purpose
Lead Caava's legacy engineering portfolio, protecting the company's largest current revenue source while supporting new customer work, necessary modernisation and progressive migration to Evolve.
Balance three priorities: Run, Grow & Modernise, and Migrate. Deliver through domain leads and specialist teams, with clear commitments from peer Heads—not by personally executing every activity.
Core Accountabilities
Protect legacy revenue and customer continuity
Keep legacy products reliable and customers supported through application support, incident improvement and safe change.
Maintain engineering coverage and recovery readiness in partnership with Platform Operations.
Build sufficient capacity and a resilient team
Match commitments to available skills; protect support and migration capacity and prevent double-booking.
Close capacity gaps through hiring, partners and cross-training.
Retain critical knowledge, strengthen succession and career paths, and develop teams without weakening customer support.
Deliver customer work and modernisation predictably
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.
Enable safe, repeatable migration to Evolve
Own the integrated customer migration plan and legacy-side readiness: business-rule discovery, data conversion, reconciliation and retirement.
Coordinate peer-owned dependencies, rehearsals, cutover and rollback readiness; build reusable upgrade and migration patterns.
Retire services, licences and capacity only after customer acceptance, data integrity, operational readiness and commercial exit conditions are met—not against arbitrary dates.
Lead an accountable, commercially sound portfolio
Own the roadmap, budget, risks and quarterly outcomes across Run, Grow & Modernise, and Migrate.
Give the CTO and ExCo evidence on delivery, capacity and revenue exposure; escalate trade-offs early with recommendations.
Challenge or reject unsafe, underfunded or under-resourced commitments.
Experience and Leadership Style
5+ years in engineering or enterprise technology, including 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, with practical experience in controlled upgrades and data migration.
Strong commercial judgement across estimation, scope, costs and acceptance; able to communicate evidence, trade-offs and recommendations at executive level.
Calm, pragmatic and collaborative leadership; transparent about risk, disciplined about commitments and invested in developing people.
Insurance, financial services or other regulated-industry experience is strongly preferred.
Lead Caava's legacy engineering portfolio, protecting the company's largest current revenue source while supporting new customer work, necessary modernisation and progressive migration to Evolve.
Balance three priorities: Run, Grow & Modernise, and Migrate. Deliver through domain leads and specialist teams, with clear commitments from peer Heads—not by personally executing every activity.
Core Accountabilities
Protect legacy revenue and customer continuity
Keep legacy products reliable and customers supported through application support, incident improvement and safe change.
Maintain engineering coverage and recovery readiness in partnership with Platform Operations.
Build sufficient capacity and a resilient team
Match commitments to available skills; protect support and migration capacity and prevent double-booking.
Close capacity gaps through hiring, partners and cross-training.
Retain critical knowledge, strengthen succession and career paths, and develop teams without weakening customer support.
Deliver customer work and modernisation predictably
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.
Enable safe, repeatable migration to Evolve
Own the integrated customer migration plan and legacy-side readiness: business-rule discovery, data conversion, reconciliation and retirement.
Coordinate peer-owned dependencies, rehearsals, cutover and rollback readiness; build reusable upgrade and migration patterns.
Retire services, licences and capacity only after customer acceptance, data integrity, operational readiness and commercial exit conditions are met—not against arbitrary dates.
Lead an accountable, commercially sound portfolio
Own the roadmap, budget, risks and quarterly outcomes across Run, Grow & Modernise, and Migrate.
Give the CTO and ExCo evidence on delivery, capacity and revenue exposure; escalate trade-offs early with recommendations.
Challenge or reject unsafe, underfunded or under-resourced commitments.
Experience and Leadership Style
5+ years in engineering or enterprise technology, including 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, with practical experience in controlled upgrades and data migration.
Strong commercial judgement across estimation, scope, costs and acceptance; able to communicate evidence, trade-offs and recommendations at executive level.
Calm, pragmatic and collaborative leadership; transparent about risk, disciplined about commitments and invested in developing people.
Insurance, financial services or other regulated-industry experience is strongly preferred.