Senior Director of Software Engineering

The Planet Group has partnered with a Boston area company to locate a Director of Software Engineering for a full time role.

This is a remote role but preference will be given to candidates local to the Boston area.

We are seeking a hands-on, execution-focused Director of Engineering to lead multiple engineering teams in delivering complex software initiatives within an established technology environment. This role is responsible for translating defined business priorities into structured engineering plans and ensuring initiatives are delivered predictably, efficiently, and with high quality. The ideal candidate thrives in fast-moving environments where clarity, accountability, and cross-functional alignment are critical to success.

Responsibilities

• Lead end-to-end execution of engineering initiatives from planning through production release
• Translate business objectives into actionable engineering roadmaps with defined milestones, sequencing, and measurable outcomes
• Establish and manage delivery cadence across multiple squads or workstreams
• Drive planning rituals including sprint planning, backlog refinement, demos, retrospectives, and milestone reviews
• Proactively identify and manage risks, cross-team dependencies, and resource constraints
• Ensure initiatives meet defined acceptance criteria and release-readiness standards
• Partner closely with Product and business stakeholders to clarify scope, priorities, and success metrics
• Coordinate with Architecture to align execution plans with established technical standards and platform direction
• Work alongside DevOps/SRE to support release readiness, environment stability, and operational transitions
• Collaborate with Data Engineering and Security teams to align on dependencies, compliance, and secure delivery practices
• Lead and develop engineering managers and senior engineers, setting clear expectations and accountability
• Reinforce strong engineering practices including code review, testing discipline, documentation, and continuous improvement
• Evaluate, select, and negotiate vendor relationships supporting engineering delivery
• Manage delivery budgets and identify cost-efficiency opportunities
• Participate in technical design discussions and maintain credibility through hands-on engagement when needed
• Encourage responsible use of AI-enabled development tools to improve efficiency while maintaining quality standards

Required Qualifications

• 5+ years of engineering leadership experience (Director or Senior Engineering Manager level) leading multiple teams or squads
• Proven track record delivering complex software initiatives with predictable timelines and measurable outcomes
• Strong background in Java-based application development environments
• Experience working within AWS cloud ecosystems
• Solid understanding of Agile delivery methodologies and execution management
• Experience working within the realm of insurance
• Experience working with vendors and managing contract negotiations
• Bachelor’s or Master’s degree in Computer Science or related technical field (or equivalent experience)

Preferred Qualifications

• Experience leading multi-squad engineering organizations in regulated environments
• Strong working knowledge of modern DevOps/SRE practices and cloud-based release management
• Experience coordinating across architecture, data, and security functions
• Demonstrated success improving delivery predictability and cross-functional alignment
• Commercial and budget oversight experience within technology organizations
• Experience driving operational maturity within established engineering platforms

Interested candidates can apply by clicking on the link.

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