Opportunities in the Upfront Portfolio


Engineering Manager- Ruby on Rails



Software Engineering, Other Engineering
Posted on Wednesday, July 3, 2024

At HopSkipDrive, our goal is to create opportunity for all through mobility.

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software and advisory services, we solve the biggest transportation challenges facing schools and school districts around the country.

Founded by three moms as a solution to their own transportation challenges, we’ve now completed more than 3.3 million rides and operate across over 13 states across the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Your role:

As an Engineering Manager, you are an accomplished engineer, having led successful projects as a Senior Engineer or Engineering Lead before directly managing teams of four or more engineers. You are fully comfortable with agile management practices, and proven project managers who have delivered many large projects successfully. As a technical leader, you are constantly tracking the team’s efficiency and quality of deliverables at SDLC and regularly adjusting processes and timelines to ensure high quality is delivered. You take responsibility for producing software that is highly available, monitorable, and maintainable over time.

While in this role, you will spend less time writing code, but there is an expectation that you still engage in some technical deliverables such as bug fixes and small features, without blocking or slowing down the progress of your team. More than writing code, you hold responsibility for identifying bottlenecks in the process and roadblocks to success for your team and clearing these roadblocks.

In this role your success will be determined by the success of your team. In particular, as a leader you are capable of identifying the most high-value projects and keeping your team focused on these projects. As part of keeping the team focused you will partner closely with Product to manage project scope and ensure the technical deliverables are met. In addition to focusing the team, you are capable of identifying headcount needs for the team and planning and recruiting to fill these needs.

As an Engineering Manager you operate as and are comfortable managing team members with different skill sets from your own. You communicate expectations clearly to all team members, solicit and deliver individual feedback frequently (not just in the scope of review periods). In addition to strong management skills, as the engineering lead you acts as a leader for the technical roadmap for the pillar. You are able to clearly communicate the timeline, scope and risks to your pillar partners, and lead the delivery of major initiatives on clear timelines. Additionally, you identify areas of strategic technical debt, do the cost/benefit analysis for resolving this debt and communicate suggested timelines for prioritizing this to the management team.

Above all, you want to build something that fundamentally improves the lives of families.

What you will do:

  • Identify and clear bottlenecks and roadblocks to the team’s success
  • Conduct weekly 1:1s with direct reports
  • Performance management - providing positive and constructive feedback
  • Foster Continuous Improvement mindset amongst team
  • Responsible for the successful planning and delivery of projects
  • Review Pull Requests and promote high code quality and testing standards on the team
  • Identify areas of strategic technical debt, do the cost/benefit analysis for resolving this debt and communicate suggested timelines for prioritizing this to the management team
  • Break up large features and long-term initiatives into smaller deliverables
  • Collaborate with VP of Engineering on technical roadmap
  • Continue to contribute to feature development and bug fixes at the level of a Sr. Software Engineer
  • Exhibit high standards when Interviewing and evaluating prospective engineering candidates

What you'll bring:

  • 5+ years of professional software engineering
  • 3+ years of professional Ruby on Rails
  • 1+ years managing software engineers
  • Excellent communication skills with technical and non-technical teammates and show a high level of emotional and professional maturity
  • A high level of craftsmanship about your work, the end experience of the user, and impact on overall product
  • Expertise with Agile Software Development practices and able to adopt the appropriate process to fit the needs of a team
  • Successful track record of delivering high-impact projects in a fast-paced environment

What you will get

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer competitive market comp, flexible vacation, FSA, medical, dental and vision, 401(k), and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is $170,000 to $200,000 year. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.

* This role will be fully remote in one of the following states AZ, CA, CO, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OH, OK, OR, SC, TN, TX, UT, VA, WA, WI**