[Hiring] Director, Engineering @Bridgeway Benefit Technologies

Role Description

Bridgeway is seeking an accomplished Director, Engineering to lead the ISSI-platform engineering organization. This role owns the strategic direction, operational execution, and people leadership for multiple engineering teams, driving alignment between engineering investment and business priorities. The ideal candidate combines deep technical credibility, proven experience leading leaders, and the strategic judgment to balance long-term platform investment with delivery commitments in a fast-paced environment. This is a remote position. East coast candidates preferred.

• Own the strategic and operational roadmap for the engineering organization, translating business strategy into departmental goals, tactical plans, and resourcing decisions.
• Lead, develop, and hold accountable a team of managers, individual contributors, offshore developers, ensuring consistent people leadership, performance management, and career development across the department.
• Manage the department's budget, headcount, and resource planning; develop and report on KPIs, and business outcomes to the VP of Engineering and broader leadership team.
• Serve as a key liaison between executive leadership and the engineering department, representing engineering priorities, risks, and progress at the leadership-team level.
• Set and champion engineering best practices across teams, including code quality standards, testing, and architecture governance, ensuring consistency across multiple teams.
• Partner with other business leaders to align technical strategy and execution with organizational objectives, and to shape multi-quarter roadmaps.
• Drive a culture of technical excellence, accountability, innovation, and continuous improvement across the department.
• Coach and develop managers and individual contributors, building bench strength and succession readiness.
• Oversee delivery of high-quality, scalable, and secure software solutions across teams, ensuring on-time delivery in an agile environment and resolving cross-team dependencies and escalations.
• Anticipate and address complex organizational challenges, including navigating ambiguity, resource constraints, and competing priorities across teams.
• Stay current with emerging technologies and industry trends, leading the evaluation and adoption of relevant innovations — including generative AI tools — and setting clear expectations for their use in day-to-day engineering work to drive productivity and quality outcomes.
• Own hiring strategy and workforce planning for the department, including hiring, onboarding, and performance evaluation of direct reports and oversight of hiring practices across teams.
• Ensure robust documentation, knowledge management, and process discipline throughout the software development lifecycle across the department.
• Provide technical guidance on complex design and architecture decisions, escalating and resolving the highest-impact technical and organizational issues.
• Own the department’s work-intake and prioritization process (e.g., Kanban), ensuring accurate estimation and holding teams accountable to committed timelines and work quality.
• Provide hands-on oversight of the offshore engineering vendor relationship, directly managing vendor-side managers and holding them accountable for high-quality delivery against agreed timelines.

Qualifications

• 7+ years of experience in software development, with at least 3 years in a people leadership role.
• Proven ability to balance strategic, long-term platform investment with near-term delivery commitments and business priorities.
• Excellent leadership, communication, and stakeholder management skills, with the ability to influence executive leadership and represent engineering priorities cross-functionally.
• Experience using generative AI tools such as Claude (preferred) and Copilot to improve productivity and deliver high-quality outcomes.
• Strong background in building and scaling SaaS applications, with demonstrated success leading multiple teams or a larger, cross-functional engineering organization.
• Hands-on experience with Azure and modern development practices; familiarity with version control systems, Git preferred.
• Experience with Agile methodologies, Kanban preferred, and driving process consistency across multiple teams.
• Demonstrated experience managing budgets, KPIs, and resource/headcount planning at a departmental or organizational level.
• Bachelor's degree in Information Technology, Computer Science, or a related field.

Company Description

Bridgeway is an Equal Opportunity Employer.