Director of Engineering

Job Description

As a Director of Engineering in our Insurance Engineering group you will lead a team that develops, maintains, and runs the custom code for our agency, billing, claims, and policy management systems.  These teams will support both our existing systems as well as the new systems to which we are moving to over the next several years.

As the 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 with both their technical and inter-personal skills as well as helping them deliver on 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), and have strong communication and strategy skills.

What you’ll do

• Guide staff in 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 develop a 3-year vision and strategy.
  • Developing narratives that you, your managers, and engineers use to effectively communicate, understand, and keep salient the vision and strategy for your systems.
  • Working with product/project managers, architects, engineering managers, and peers to develop a concrete roadmap that balances the business’s needs with the need for ongoing evolution and maintenance of our systems.
  • Participating in the discussion on the feasibility of new features, the cost to implement them, and the possible implementation timelines given current priorities and staffing.
• Influence and support the maturation of engineers and engineering practices by:
  • Participating in the creation and education of standards, practices, 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 other’s code.
  • Helping to define what “quality” means for services throughout their lifecycle.  This includes things like auditability, deployment practices, documentation requirements, evolvability, 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 we must deal with and educating staff on what is required to meet these needs.
  • 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, hiring, and maintaining staff that bring in diverse thoughts.  This includes providing timely, candid, and respectful feedback on accomplishments and misses.
  • Developing an onboarding and career progression curriculum that helps guide individuals in developing their skills through deliberate practice, self-mediated learning, and mentorship.
  • Coaching engineering managers on the differences between, and techniques for, managing individual contributors, peers, and superiors.
  • Coaching engineering managers and teams on how to effectively communicate and discuss diversity of opinions while respecting differences and committing to decisions.
  • 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.
• Monitor and improve the financial sustainability of your services by:
  • Developing, monitoring, and reporting on financial models (e.g., unit costs, run rates) for each service including new feature development and ongoing maintenance.
  • Supporting budget planning by providing cost-projections and well-reasoned investment plans based on the department’s strategy, vision, and expected growth.
  • Educating staff on the basics of the financial health of the teams and services and working with them to develop methods for improvement.

This might describe you

• Worked as an 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.
• Demonstrable ability to comprehend, decompose, and construct solutions in complex domains.  Experience in developing products in at least three complicated domains.
• Deep, well-structured conceptual thinking and the ability to effectively communicate technical or abstract concepts to technical and non-technical people
• Highly proficient with, and able to stay current on, the full development and deployment stack, e.g.:
  • Languages: C#, 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
• Experience in coaching individuals, with varying degrees of existing competency and communication/learning styles, in technical and non-technical skills.

Other things to note 

• This role can be worked from any U.S. remote location. 
• 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. 

Say hello to Hagerty 

Hagerty is an automotive enthusiast brand and the world’s largest membership organization. Along with being a best-in-class provider of specialty insurance for enthusiasts, Hagerty is also home to the Hagerty Drivers Foundation, Garage + Social, Hagerty Drivers Club, Marketplace, and so much more. Committed to saving driving for future generations, each and every thing Hagerty does is dedicated to the love of the automobile. 

Hagerty is a rapidly growing company that values a winning culture. We provide meaningful work for and invest in every single team member. 

At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference.  We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world. 

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Vermont, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email recruiting@hagerty.com for compensation, comprehensive benefits and the perks that set us apart.