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Director Engineering (Remote, US)



This job is no longer accepting applications

See open jobs at Openly.
Posted on Wednesday, January 24, 2024

Openly is rebuilding insurance from the ground up. We are re-envisioning and enhancing every aspect of the customer experience. Doing this requires a rapidly growing team of exceptional, curious, empathetic people with a wide range of skill sets, spanning technology, data science, product, marketing, sales, service, claims handling, finance, etc.

Now is the perfect time to join the journey. Here’s why

  • It’s working. We’re in multiple states and on our way to operating countrywide. We have thousands of agents selling our product and millions of dollars of annual customer premiums.
  • We’re well-backed & stable. We closed our $100M Series D fundraise. We are supported by some of the top investors globally, including Google’s “Gradient” AI-focused fund, Obvious Ventures, Advance Venture Partners, Eden Global Partners, and Clocktower Technology Ventures.
  • It’s not too late! Despite this traction and stability, we’re still early enough in the journey that there’s time to make a real difference during Openly’s formative period.

If you’d like to understand more about Openly’s mission, consider checking out this video (https://vimeo.com/267654520) from a company pitch we gave several years ago at Techstars.

As an Engineering Director at Openly, you will be responsible for driving alignment with and execution of the engineering strategies for supporting the business within your directorate and across engineering. You will be leading and developing Engineering Managers and Staff Engineers, and collaborating closely with the VP of Engineering, fellow directors, and other senior leaders across the organization to plan and prioritize milestones, evaluate outcomes, and translate those evaluations into next steps. You will play a vital role helping us build sustainable, high quality technology and teams.

Key Responsibilities

  • Lead a team of Engineering Managers and Staff Engineers to effectively manage projects and people within Engineering
  • Effectively manage time in the following areas:

Leading, developing, supervising Engineering Managers and Staff Engineers

Planning & prioritizing milestones for people, projects, & processes

Evaluate the timing and outcomes of those milestones

  • Translate those evaluations into next steps
  • Collaborate closely with the VP of Engineering
  • Build and maintain strong relationships with the CTO and other senior leaders across the organization
  • Partner with Product Managers to staff cross-functional teams to make impactful changes as quickly and autonomously as possible
  • Build and maintain awareness and context of the people side of things through 1:1's with the Engineering Managers who report to you, and skip-level meetings with the engineers who report to them
  • Build and maintain awareness and context of the technical details of initiatives through 1:1's and architectural discussions with the Staff Engineers who report to you, as well as reviews of their work
  • Build and maintain a strong understanding of core insurance concepts across multiple business domains
  • Connect the right person or team to the right work
  • Identify and develop key talent to promote internal career growth
  • Foster a culture of transparent feedback and communication
  • Actively seek ways to improve engagement and happiness on the team
  • Be curious in the face of uncertainty; gain the necessary knowledge or set up the necessary milestones to resolve that uncertainty
  • Partner closely with the management team, HR, and Recruiting to attract, recruit, provide professional development opportunities for, and level-up diverse teams of high-quality engineers

Our stack

  • Backend/Core: Go & Postgresql
  • Frontend: Browser-based, VueJS, Webpack, Nuxt &, Tailwind
  • Research/Data Science: R, ArcGIS, H2O, & Python
  • Infrastructure: Google Cloud, specifically Cloud Run, Cloud Build, and CloudSQL, managed with Terraform. We use GitHub for code hosting and CircleCI for running our CI/CD pipelines.
  • Remote work tools: Slack, Zoom, Donut



  • Typically requires 12+ years of experience in a broad software engineering domain, 5+ years of that within people management, and 2+ years of that as successful experience leading managers
  • Sustained track record of building and leading software engineering teams that have created improvements in business-critical systems around functionality, stability, performance, and scalability
  • Demonstrated ability guiding teams to deliver multiple complete projects from start to finish in reasonable overlapping time frames
  • Experience guiding and growing teams of teams, balancing engineering needs with business requirements
  • Experience developing a strategy or roadmap for your teams
  • Ability to think strategically and execute methodically
  • Bachelor’s degree or equivalent related software engineering experience
  • Experience or familiarity with Agile methodologies


  • Defaults to a collaborative mindset to work with multiple stakeholders to maximize our resources
  • No Egos - focuses on the best outcomes for the engineering organization and the company over ownership of any particular project, process, or people
  • Demonstrates high engagement and low attachment
  • Excellent written and verbal communication


  • Comfortable making decisions, and owning and being accountable for results
  • A high level of comfort navigating and making decisions and recommendations in environments of ambiguity

Problem solving

  • Bias towards action over perfection
  • Investment approach - considers long-term horizons to ensure immediate solutions build towards goals
  • Iterative approach - optimizes for a regular cadence of small meaningful iterations
  • When presented with a complex problem, process, or existing system you are consistently able to reduce the complexity to get more done with less work

Hiring & Team Building

  • Strong track record for hiring, retaining, and developing talent
  • Passion for fostering DE&I


Compensation & Benefits:

The base compensation for this position will be commensurate with experience and qualifications. Actual compensation will be determined based on various factors including the candidate's qualifications, skills, and experience.

Base Salary Range
$190,800$286,200 USD

The target compensation for this position will be determined based on the successful candidate's experience and skills. We are committed to providing a compensation package that not only reflects the responsibilities and requirements of the role, but also the unique expertise that the chosen candidate will bring to our team.

Target Salary Range
$207,000$238,000 USD

Benefits & Perks

  • Remote-First Culture - We supported #remotelife long before it was a given. We'll keep promoting it.
  • Competitive Salary & Equity
  • Comprehensive Medical, Dental, and Vision Plan Offerings
  • Life and disability coverage including voluntary options
  • Competitive PTO - 20 days and 11 paid holidays (including floating holidays) per year under the Company’s vacation and holiday policies.
  • Parental Leave - 12 weeks paid for eligible employees
  • 401K Company Contribution - Openly contributes 3% of the employee's gross income, even if the employee does not contribute.
  • Work-from-home stipend - We provide a $1,500 allowance to spend on setting up your home workplace
  • Annual Professional Development Fund: Each employee has $2,000 in professional development (PD) funds to spend on activities or resources annually. We want each Openly employee to achieve personal and professional success and to feel supported, confident, and informed about improving their efficiency and productivity.
  • Be Well Program - Employees receive $50 per month to use towards your overall well-being
  • Paid Volunteer Service Hours
  • Referral Program and Reward

Depending on position, Employees generally are eligible for cash incentive compensation, including commissions for sales eligible roles. In all cases, eligibility for compensation and benefits is subject to applicable plan and policy terms in effect from time to time.

U.S. Citizens, Green Card Holders, and those authorized to work in the U.S. for any employer and currently residing in the US will be considered.

Openly is committed to equal employment opportunity and non-discrimination for all employees and qualified applicants without regard to a person's race, color, sex, gender identity or expression, age, religion, national origin, ancestry, ethnicity, disability, veteran status, genetic information, sexual orientation, marital status, or any characteristic protected under applicable law. Openly is an E-Verify Employer in the United States. Openly will make reasonable accommodations for qualified individuals with known disabilities under applicable law.

This job is no longer accepting applications

See open jobs at Openly.