Ruby Engineering Manager

Hagerty is an automotive enthusiast brand and the world’s largest membership organization, dedicated to preserving car culture for future generations. As a Ruby Engineering Manager in the Dealer Technologies group, you will lead a team focused on designing and building dealership websites, while also fostering team growth and ensuring high-quality engineering practices.

Responsibilities:

• Guide staff in understanding and delivering on the company’s long-term goals by:
• Working with your manager to develop a deep and nuanced understanding of the company’s goals and, working with staff, develop quarterly plans to implement associated features
• Effectively and continually communicate and keep salient the vision, strategy, and roadmap. Be able to discuss how each team member’s work is contributing to those ends
• Participating in the feasibility assessment of new features, the cost to implement them, and the possible implementation timelines given current priorities and staffing
• Ensuring your services protect and appropriately manage the company’s data and user’s privacy
• Influence and support the maturation of engineers and engineering practices by:
• Educating engineers of our standards, practices, and idioms and ensuring adherence to them. This will require you to have a deep knowledge of these things as well as the reasoning behind them
• Educating engineers on, and evaluating code for, quality. This includes things like auditability, deployment practices, documentation requirements, evolvability, maintainability, performance monitoring, operational readiness, testing regimes, security evaluation, and risk mitigation
• Coach engineers on effective ways to share knowledge within and between teams. This includes effectively communicating with other groups regarding your work upon which they depend
• Coaching engineers on the art of identifying and evaluating the many tradeoffs that come up during system development. For example, between feature-rich frameworks and in-the-moment supportability, or between user experience and security consideration
• Develop a healthy and dynamic team that values and participates in the growth of individuals, the team, and the company by:
• Recruiting, hiring, and maintaining staff that bring in diverse thoughts. This includes providing timely, candid, and respectful feedback on the staff’s accomplishments and misses
• Running an onboarding and career progression curriculum that helps guide individuals in developing their skills through deliberate practice, self-mediated learning, and mentorship
• Coaching engineers on the application of psychological and sociological topics like trust, perspective taking, critical thinking, path dependence, emotional contagion, and deliberate practice
• Maintaining a workload that balances new feature development, beneficial technical and process improvements, and staff’s learning and development
• Tracking, reporting on, and responding to qualitative and quantitative measures of team health and capacity
• Facilitate the collaboration within your teams and between your teams and the rest of the company by:
• Collaborating closely with functionally-related teams, product/module owners, technical product managers, and operations to help communicate status and make the best engineering decisions
• Coaching team members on effective cross-team communication
• Monitor and improve the operational and financial sustainability of your services by:
• Understanding and monitoring key operational metrics (e.g., consumption of metered 3rd party resources, infrastructure utilization, performance over time) for your services. Understand and communicate how different technical decisions will impact these metrics
• Supporting budget planning by articulating team needs, in the context of the vision, strategy, and roadmap. This includes predicting and justifying the need for increasing or decreasing team size
• Educating staff on the basics of evaluating the operational health of the team and its services and working with them to propose methods for improvement

Requirements:

• Worked as a senior engineer, team lead, or manager on at least three large-scale, complex systems during initial development or major feature development and at least one consecutive year of product support and minor feature enhancements
• Beginning to identify beneficial behavioral and organizational concepts, patterns, and principles and attempt to apply them across a variety of different situations
• Effectively communicates technical or abstract concepts to other engineers, technical and non-technical/business peers, and your manager
• Beginning to define a decision-making process that allows you to identify and gather applicable data/facts, weigh tradeoffs, and mitigate any of your existing biases without getting paralyzed when working with incomplete information. Decisions to be made are usually well-defined and scoped to your immediate work/team
• Experience in coaching individuals, with varying degrees of competency and differing communication/learning styles, in technical and non-technical skills
• Proficient with, and the ability to stay current on, development and deployment technologies such as: Languages: Ruby, Terraform, Typescript, Interservice Communication: HTTP API patterns (ReST, RPC, GraphQL), brokered and non-brokered messaging, Security: SAML, OAuth 2, OIDC, data encryption, signing, CSRF, System Performance: load testing, application profiling, OS profiling, Operational Readiness: diagnostic and audit logging, metrics, tracing, monitoring, alerting, Deployment: VMs, containers, cloud providers, configuration management, canary deployments, Network: TCP/IP, HTTP, Firewalls, load balancers