Director of Software Engineering

Hagerty

1d•Remote

About The Position

As the Director of Software Engineering in our Foundations Engineering group, you will lead teams that are responsible for services that sit at the foundation of nearly everything we do. They include the creation, use, and management of digital identities, generation, storage and management of documents, acquisition and processing of payments, and creation, use, and management of our core vehicle data. As a director of engineering, you will have a small set of managers reporting directly to you. It will be your job to grow them and their teams in both technical and interpersonal skills as well as helping them deliver their work. You will also be responsible for effectively communicating, to technical and non-technical individuals, what your team is working on and any needs the engineering team may have. You must be deeply technical (e.g., still comfortable writing and reviewing complicated code), have strong communication skills, and the ability to develop and execute a strategy.

Requirements

Worked as a director 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

Nice To Haves

Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable.
For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.

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.
Develop narratives that you, your managers, and engineers use to effectively communicate, understand, and keep salient the vision and strategy for your systems.
Participate in discussions on the feasibility of new capabilities, the cost to implement them, and the possible implementation timelines given current priorities and staffing.
Review 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.
Help 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.
Develop, 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.
Educate 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.
Provide timely, candid, and respectful feedback on accomplishments and misses.
Coach engineering managers on the differences between, and techniques for, managing individual contributors, peers, and superiors.
Coach staff on core software development concepts, and appropriate application thereof, such as critical thinking, encapsulation, design patterns, and breaking/non-breaking API changes.
Develop 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.
Coach managers on effective cross-team communication.
Support 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.
Support 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.
Educate staff on monitoring the financial health of their teams and services and working with them to develop methods for improvement.