Head of Legacy Engineering and Migration Enablement

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.

Weekly Success Measures

Application support and continuity

• Critical legacy application incidents resolved within agreed SLAs (%); overdue critical application incidents.
• 100% resolved within agreed SLAs; 0 overdue critical application incidents.

Capacity and capability

• Next 2 weeks’ committed demand covered by named, available capacity, assessed by skill.
• 100% covered; 0 unapproved double-bookings; minimum support/on-call coverage maintained.

Delivery and modernisation

• Due SOW/project and WebLogic/upgrade milestones accepted on time (%);
• ≥90% completion in each workstream; 0 critical defects at acceptance.

Migration and legacy exit

• Due legacy-side migration milestones accepted on time (%); critical reconciliation exceptions at cutover.
• ≥90% completion; 0 unresolved critical reconciliation exceptions at cutover; all readiness/exit gates met.

Revenue-risk reduction

• Revenue-critical incident, lifecycle and resourcing corrective actions completed by their due dates.
• 100% of actions due completed; 0 overdue revenue-critical actions.

First 90 Daysys 1–30

Understand & Stabilise

• Establish a shared baseline of customers, revenue, commitments, capacity and lifecycle risks. Confirm minimum safe coverage and agree the most urgent actions with the CTO.ays 31–60

Agree the Plan

• Agree a resourced Run, Grow & Modernise, and Migrate roadmap, including WebLogic upgrades, customer migration waves and peer-owned readiness gates. Put intake controls and priority staffing actions in motion.ays 61–90

Demonstrate Progress

• Show control of capacity and forecasts; deliver an agreed milestone and a migration rehearsal or customer proof point with reconciliation. Confirm reusable patterns and present the quarterly portfolio review to the CTO and ExCo.

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.

Leadership Approach

• Combine strategic judgement with practical design depth; make timely decisions and maintain standards under delivery pressure.
• Lead calmly, surface risks early, communicate plainly and build teams that deliver without constant escalation.