Head, Technology Delivery

We are looking for a Head of Technology Delivery to join our team. The successful candidate will report directly to the CTO and serve as the operational backbone of the Technology department.

About the Role

The Head of Technology Delivery will own end-to-end product quality, streamline delivery processes, and lead the strategic adoption of internal AI tools across the organization. The ideal candidate will have a proven track record of optimizing agile delivery frameworks, test strategies, and quality assurance practices in complex, multi-team environments.

Key Responsibilities

• Product Quality & Delivery Excellence: Own end-to-end quality standards, testing frameworks, and release governance to ensure high-performing technology deployments.
• Process Improvement & Operational Efficiency: Audit delivery processes, implement repeatable operating models, and drive agile best practices to reduce cycle times and eliminate bottlenecks.
• AI Strategy & Integration: Lead internal AI adoption by identifying high-leverage workflows, establishing ROI frameworks, and deploying tools that boost productivity and delivery quality.
• Leadership & Cross-Functional Alignment: Partner with CTO and school operations leaders to align technology delivery timelines with organizational needs and the academic calendar.
• Portfolio Health & Metrics: Establish health KPIs, track team velocity, and proactively mitigate risks across all active product initiatives.

Qualifications

• 10+ years of experience in technology delivery, engineering program management, or a related field, with at least 5 years in a senior leadership role.
• Proven track record of optimizing agile delivery frameworks, test strategies, and quality assurance practices in complex, multi-team environments.
• Hands-on experience evaluating and implementing AI/ML productivity tools responsibly within an enterprise setting.
• Bachelor’s degree in Computer Science, Information Technology, Engineering, or an equivalent combination of education and experience.

Competencies

• Strategic Execution: Translates high-level CTO priorities into actionable, structured project plans with clear accountabilities and measurable timelines.
• Continuous Improvement: Identifies operational inefficiencies and systematically institutes scalable solutions that raise delivery velocity and standard of quality.
• Influencing & Communication: Engages credibly across executive leaders, technical engineers, and non-technical stakeholders to build alignment and consensus.
• Bias for Action: Operates with high ownership and agility to resolve technical bottlenecks and dependencies in a fast-paced environment.

Compensation, Benefits & Perks

• Compensation Range: $250,000-$275,000 USD
• Day-One Health & Wellness: Medical, dental, and vision coverage starting your first day (SA covers 82% of our core medical plan), plus a free One Medical membership and confidential mental health support via EAP/Talkspace.
• Financial Security: 403(b) retirement plan with a 3% employer match, up to $2,400/year in employer HSA contributions, employer-paid life/disability insurance, and Public Service Loan Forgiveness (PSLF) eligibility.
• Time to Recharge: Generous paid time off, paid holidays, and paid parental leave.
• Perks & Stipends: A $50/month cellphone stipend ($600/year), pre-tax commuter benefits, backup family care, and performance-based earning incentives.