Director - Product Development

As the Product Leader, you will own the product strategy, customer retention, and migration roadmap for Redwood's legacy workload automation portfolio. You will maximise customer lifetime value and position migrations as expansion opportunities, not churn events.
The candidate will have responsibilities across the following functions:
Cross-Functional Leadership:
Partner with the Product team to ensure migration blockers are addressed in the roadmap (feature parity, migration utilities, customer-specific integrations).
Collaborate with Engineering to prioritise defect fixes, security patches, and compliance requirements while minimising investment in legacy platforms.
Work with Customer Success to design migration engagement models: discovery workshops, migration planning, technical validation, go-live support.
Support Sales with migration business cases and competitive positioning.
Team Leadership and Mentorship:
Develop Product Owners responsible for backlog management, sprint ceremonies, and delivery execution.
Model product management best practices: customer-centric discovery, data-driven prioritisation, outcome-based roadmapping, transparent communication.
Build PO capability in migration management, customer segmentation, churn risk assessment, migration planning, and technical enablement.
Requirements:
5-7 years in product management with demonstrated track record of shipping complex B2B enterprise software.
Legacy product management experience: Sustained platforms while building migration paths to modern architectures.
Customer retention expertise: Prevented churn during platform transitions, positioned migrations as value-add vs. disruption.
Enterprise software domain knowledge: Workload automation, ERP integration, cloud infrastructure, or mission-critical operations software preferred.
Cross-functional leadership: Partnered with Engineering, Sales, CSM, and Support to balance competing priorities and deliver customer outcomes.
Analytical rigour: Used data (renewal rates, support ticket trends, usage telemetry) to inform prioritisation and predict churn risk.
Preferred Experience:
8+ years in product management with portfolio-level accountability for multiple products or customer segments.
Migration strategy execution: Led customer migrations at scale (100+ accounts), developed segmentation models, built migration tooling/playbooks.
Workload automation or IT operations domain.
Deep understanding of job scheduling, batch processing, ERP integration, SAP workflows, or cloud orchestration.
Team leadership: Hired, developed, and retained Product Owners or junior PMs in distributed/offshore models.

Experience
12-16 yrs