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.