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Head of Engineering Strategy

Seeking a deeply technical, highly collaborative engineering leader to help shape how their engineering organization operates, modernizes, and scales.

The Head of Engineering Strategy will own and drive cross-engineering technical strategy, modernization, standards, and major engineering initiatives. This person will work closely with their experienced senior engineers and technical leads, leveraging their deep knowledge of a proprietary platform while bringing strong technical leadership, modern engineering practices, and clear execution.

This is not a traditional people-management role. The focus is on technical leadership across the engineering organization: bringing strong engineering voices together, establishing direction, driving adoption, and ensuring important technical initiatives move from discussion to implementation.

The role reports directly to the VP of Product & Engineering.

What You'll Do

• Own and drive engineering modernization across the organization, including the adoption of AI-assisted development tools, modern engineering workflows, and new technologies that improve speed, quality, and developer effectiveness.
• Own the evolution and adoption of engineering-wide standards around unit testing, automated testing, code review, CI/CD, release processes, technical documentation, and development practices, in partnership with existing engineering leads.
• Lead cross-team technical and architectural discussions, bringing together senior engineering expertise to evaluate tradeoffs, establish clear direction, and drive decisions through implementation.
• Continuously evaluate new technologies, tools, and engineering approaches, and lead promising ideas from experimentation through successful adoption.
• Bring senior engineers and technical leads together around important cross-team initiatives and ensure discussions result in clear decisions, ownership, and follow-through.
• Work alongside existing technical leaders to strengthen practices around reliability, observability, performance, infrastructure, environments, backups, and overall platform health.
• Help identify when additional technical expertise or specialized roles would benefit the organization.
• Serve as a trusted technical counterpart to the VP of Product & Engineering on major engineering questions, technical strategy, and organizational improvement.

What They're Looking For

• Strong hands-on software engineering background with the ability to review code and engage deeply in technical discussions.
• Significant experience in senior technical leadership across multiple engineering teams.
• Strong understanding of software architecture, engineering practices, and scalable SaaS systems.
• Exceptional awareness of current and emerging engineering technologies, AI-assisted development, developer tooling, frameworks, platforms, and modern software-development practices, with a demonstrated habit of continuously exploring, evaluating, and adopting new approaches.
• Experience with automated testing, CI/CD, observability, reliability, and cloud-based SaaS environments.
• Ability to lead and influence highly experienced engineers without relying solely on formal reporting authority.
• Strong technical judgment and the ability to turn complex or competing technical viewpoints into clear direction and practical action.
• Excellent communication skills, including the ability to explain complex technical topics to non-engineering leadership.
• A track record of driving engineering-wide initiatives from idea through adoption and implementation.
• Ability to combine strong technical opinions with respect for existing systems, institutional knowledge, and experienced engineering teams.

What Success Looks Like (within the first year)

• AI-assisted development practices are being used effectively and consistently across Engineering.
• Unit testing and automated testing have a clear, practical strategy and are being adopted across teams.
• Engineering standards and development practices are more consistent across the organization.
• New technologies and engineering tools are being evaluated and adopted more quickly where they provide meaningful value.
• Senior engineering discussions result in clear decisions, actions, and implementation.
• Important technical improvements continue moving forward alongside feature development.
• Engineering becomes more efficient while maintaining or improving quality, stability, and reliability.

The Ideal Candidate

• You are deeply technical, highly current, pragmatic, and execution-oriented.
• You actively stay ahead of changes in software engineering, AI, tooling, and development practices rather than waiting for established approaches to become industry standard.
• You are comfortable working with experienced engineers who may have strong and differing opinions. You respect their knowledge, listen carefully, challenge assumptions, and know when to push toward a decision.
• You have a strong backbone, low ego, and you lead through technical credibility, collaboration, sound judgment, and execution.

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