Director of Software Engineering

Hagerty is a company built by drivers for drivers, dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. The Director of Software Engineering will lead teams responsible for foundational services, including digital identities and payment processing, while also focusing on team development and effective communication across the organization.

Responsibilities:

• Guide staff in delivering on the company’s long-term goals by:
• Working with your manager to develop a nuanced understanding of the company’s goals and use that to develop a long-term strategy and quarter-by-quarter roadmap for your group
• Developing narratives that you, your managers, and engineers use to effectively communicate, understand, and keep salient the vision and strategy for your systems
• Participating in discussions on the feasibility of new capabilities, the cost to implement them, and the possible implementation timelines given current priorities and staffing
• Reviewing the design of capabilities, in conjunction with the architecture team, to ensure it is ready for your teams to work on and support your managers in explaining, breaking down, estimating, and delivering the work
• Influence and support the maturation of engineers and engineering practices by:
• Participating in the creation and education of standards, practices, and idioms as well as reviewing the implementations of these things within your teams. This will require the ability to both write example code and review others’ code
• Helping to define and educate on what 'quality' means for services throughout their lifecycle. This includes things like auditability, business continuity, deployment practices, documentation, maintainability, performance monitoring, testing regimes, security, and risk mitigation
• Developing, with the help of our legal and security offices, an understanding of the various auditing, compliance, regulatory, and security regimes (e.g., SOC, SOX, ISO27001/2) we must deal with and educating staff on their roles in those processes
• Educating engineering managers on the art of identifying and discussing the tradeoffs between various business interests, technical concerns, financial requirements, and more
• Develop a healthy and dynamic team that values and participates in the growth of individuals, the team, and the company by:
• Developing practices for recruiting and hiring staff that bring in diverse thoughts and support their development of skills through deliberate practice, self-directed learning, and mentorship. This includes providing timely, candid, and respectful feedback on accomplishments and misses
• Coaching engineering managers on the differences between, and techniques for, managing individual contributors, peers, and superiors
• Coaching staff on core software development concepts, and appropriate application thereof, such as critical thinking, encapsulation, design patterns, and breaking/non-breaking API changes
• Developing qualitative and quantitative measures of team health and capacity used by managers to track, report on, and respond to their teams. Coach managers on how to use these measures to effectively manage team workloads, develop team members, and identify staffing needs
• Facilitate the collaboration within your teams and between your teams and the rest of the company by:
• Collaborating closely with functionally related teams, product/business leads, and operations to ensure technology teams are delivering the company’s initiatives using the company’s processes
• Coaching managers on effective cross-team communication
• Supporting managers in identifying, understanding, and delivering dependencies other teams currently, or will soon, have on them and dependencies they have on other teams
• Monitor and improve the financial sustainability of your services by:
• Developing, monitoring, and reporting on financial models (e.g., unit costs, run rates, cap/op expenses) for each service including new feature development and ongoing maintenance
• Supporting annual budget planning by providing cost-projections and well-reasoned investment plans based on the department’s strategy, vision, and expected growth. Monitor performance against plan throughout the year
• Educating staff on monitoring the financial health of their teams and services and working with them to develop methods for improvement

Requirements:

• Worked as a directory or engineering manager on at least three different large-scale systems during initial development or major feature development and at least three consecutive years of production support
• Reliably identifies beneficial behavioral and organizational concepts, patterns, and principles and wisely discern when, and when not, to apply them across a variety of different situations
• Effectively communicates technical or abstract concepts to other engineers, technical and non-technical/business peers, your manager and their peers
• Consistently employs 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
• Experience in coaching individuals, with varying degrees of competency and differing communication/learning styles, in technical and non-technical skills
• Highly proficient with, and able to stay current on, the full development and deployment stack, e.g.: Languages: C#, Terraform, Typescript; Interservice Communication: HTTP API styles (ReST, RPC, GraphQL), brokered and non-brokered messaging; Security: SAML, OAuth 2, OIDC, data encryption, signing, CSRF, STRIDE analysis; 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