Senior Director of Engineering, Core Product

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of the daily execution and engineering integrity of Assessment, Curriculum, and Scheduling product clouds.

• Collaborate with engineering managers, product leadership, and cross-functional teams to translate the roadmap into dependable, high-quality software.

• Spearhead the shift from ad-hoc coding to specifications-driven development.

• Set standards for writing, versioning, and utilizing specifications.

• Promote AI-assisted development while ensuring quality is upheld.

• Define and apply delivery, quality, and reliability metrics to inform decisions and highlight potential risks.

• Establish commitments, clarify completion standards, define ownership, and tackle underperformance.

• Foster a culture of continuous improvement within engineering teams.

• Implement consistent planning, building, reviewing, testing, and release standards across three product clouds.

• Oversee sprint health, throughput, quarterly deliveries, blockers, and trade-offs related to scope, quality, and timelines.

• Manage quality, reliability, Change Failure Rate, Escaped Defect Rate, bug backlog, SLA compliance, and production uptime.

• Recruit, mentor, coach, and develop engineering managers; facilitate calibration and performance cycles; build a strong leadership bench.

• Collaborate effectively with product, design, and customer-facing leadership.

• Enhance specifications, estimation, definition of done, code review, release, and metrics practices.

• Establish operational rhythms and baseline metrics.

• Initiate and expand spec-driven, AI-augmented engineering methodologies.

⛳️ Requirements

• Over 10 years of experience in software engineering, including more than 5 years in leadership roles.

• Proven experience managing engineering managers; managerial experience at a higher level is essential.

• Successful track record in overseeing multiple teams or product lines simultaneously and delivering results predictably at scale.

• Experience leading an AI transformation within an engineering organization.

• Proven ability to drive the adoption of AI-assisted development and/or specifications-driven practices.

• Metrics-oriented leadership style; proficiency with DORA, defect/escape rates, and SLA attainment.

• Capability to hold teams accountable and directly address performance issues.

• Proven commitment to engineering quality and reliability.

• History of cultivating a culture of continuous improvement.

• Strong operational instincts across active portfolios.

• Exceptional cross-functional collaboration with product and customer-facing teams.

• Ability to communicate clearly and candidly with executives.

• Experience in B2B SaaS environments.

• Familiarity with cloud/pod models and modern delivery tools, including Jira, CI/CD, observability, and automated testing.

• Preferred experience in higher education technology or regulated/enterprise sectors.

• Preferred experience in scaling teams through periods of rapid growth and process maturity.

• Hands-on experience with specifications-driven workflows or AI development tools is preferred.

🏝️ Benefits

• Comprehensive healthcare, dental, and vision coverage.

• Employee-only coverage: 99% to 65% of monthly premiums.

• Employee plus dependents: 77% to 50% of monthly premiums.

• Spring Health for mental health support.

• XP Health for vision benefits.

• Carrot Fertility for family planning assistance.

• One Medical for primary care services.

• Health Savings Accounts (HSA).

• Flexible Spending Accounts (FSA).

• Safe Harbor 401(k) plan available from the first day of employment.

• 4% employer match on total compensation, subject to federal limitations.

• Unlimited Paid Time Off.

• Remote-first work environment.

• Equity grants aligned with role and tenure.

• Equity grants reviewed and adjusted with promotions.

• Up to 6 weeks of Paid Bonding Leave at 100% of base pay for all parents.

• An additional 6 weeks of Paid Medical Recovery Leave at 100% of base pay for birthing parents, totaling up to 12 weeks.