Senior Engineering Manager, Co-Intelligent Coaching

Accountabilities:: Lead multiple engineering squads responsible for delivering AI-powered coaching experiences, from prototyping and development through production, maintenance, and on-call support. Own delivery planning, sprint shaping, prioritization, backlog management, and estimation, making clear decisions about competing priorities and team capacity. Improve engineering cycle time while maintaining high standards for software quality, reliability, and operational performance. Maintain hands-on technical involvement by contributing production code, reviewing architecture, identifying design weaknesses, and supporting incident response. Partner closely with Product Strategists to align product scope, technical feasibility, delivery costs, and timelines, ensuring clear ownership and effective collaboration. Guide the development of AI-driven member experiences, including goal setting, food guidance, daily reflection, and appropriate transitions to human coaching. Establish and promote effective standards for AI-assisted engineering, including agent workflows, evaluation practices, and measurable quality expectations that can be adopted across teams. Coach and develop engineering managers and emerging technical leaders, providing direct feedback, supporting performance improvement, and building greater leadership accountability. Plan future team capacity, headcount, skill distribution, and onboarding approaches to help new engineers become productive quickly in an AI-enabled development environment. Strengthen engineering operations through effective CI/CD, logging, monitoring, telemetry, and incident management practices. Identify and lead cross-functional improvements that address broader engineering challenges, bringing peers together to resolve issues beyond individual team responsibilities. Requirements: At least 8 years of software engineering experience, including 4 or more years of direct engineering management experience. Demonstrated success developing another leader, such as an engineering manager, technical lead, or engineer who has taken on meaningful leadership responsibility. Proven experience delivering mission-critical software to production and maintaining accountability for its ongoing performance and reliability. Experience owning team prioritization, estimation, delivery commitments, and capacity trade-offs, including communicating difficult decisions clearly. Strong people leadership skills, including providing direct developmental feedback and supporting team members through performance challenges. Current or recent hands-on experience shipping production code in at least one of the following areas: backend development (Ruby, Python, or similar), web development (React), iOS, or Android, with the technical breadth to assess architecture across other layers. Comfort working with an expert-generalist engineering model, where team members contribute across backend, web, and mobile systems, with an understanding of its opportunities and potential risks. Practical experience directing AI agents through real-world production changes, alongside a thoughtful understanding of where AI-assisted development improves productivity and where it may introduce rework. Experience building and evaluating AI products, including deploying agents to production, monitoring their behavior at scale, and using evaluations to measure the impact of prompt or model changes. Strong understanding of CI/CD, logging, monitoring, and telemetry, with the ability to assess the operational health of engineering systems. Excellent written communication skills, with the ability to document decisions, expectations, and technical standards clearly and consistently. Familiarity with technologies such as Ruby on Rails, Python (Flask or FastAPI), React, Swift, SwiftUI, Kotlin, PostgreSQL, GraphQL, AWS, Docker, Kubernetes, GitLab, Datadog, and PagerDuty. Benefits: Competitive base salary with generous annual cash bonus. Equity grants. Employee Stock Purchase Plan (ESPP). Remote-first work culture. Flexible Time Off to support rest, personal commitments, and work-life balance. Generous parental leave. Health, dental, and vision insurance with above-market employer contributions. 401(k) retirement savings plan. Lifestyle Spending Account (LSA). Mental health support solutions. Additional employee benefits and programs.