Engineering Director, HopSkipDrive


+Equity in the form of Stock Options

Ruby on Rails
Expert level
Remote in US

More information about location


Safe youth transportation solution

Open for applications


Safe youth transportation solution

201-500 employees


Open for applications


+Equity in the form of Stock Options

Ruby on Rails
Expert level
Remote in US

More information about location

201-500 employees


Company mission

To use technology, operational expertise, and new thinking to help kids reach their full potential by providing a safe, dependable way to get them where they need to be.


Who you are

  • You should be obsessed with creating high-functioning, engaged and motivated organizations
  • You are also an excellent communicator and can simplify technical concepts in a way to explain them to non-technical partners, and take business direction and explain it to the technology team in a way that inspires and guides them
  • Director level (or higher) experience at technology focused start-ups. Additional leadership experience with established, larger companies is a plus
  • 5+ years experience as a professional software engineer (IC)
  • 3+ years of professional Ruby on Rails
  • 2+ years experience managing software engineers
  • 2+ years in a senior leadership role, specifically managing/leading other managers and organizations
  • A mindset of Continuous Improvement
  • Excellent oral and written 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 directing multiple teams delivering high-impact projects in a fast-paced environment
  • Experience leading a diversity-focused hiring process for individual contributors and managers
  • Above all, you want to build something that fundamentally improves the lives of families

What the job involves

  • As the first Director of Engineering at HopSkipDrive, you will lead a significant area of our engineering organization, focusing on developing products, systems, and processes for ensuring the operational excellence of all HopSkipDrive rides
  • This group will include several cross-functional teams focused on Ruby on Rails, ReactJS, and mobile application development
  • Your direct reports will be the engineering managers for those teams.You will report to the VP of Engineering
  • One of your primary concerns will be ensuring smooth execution of complex deliverables. To that end, you will focus on ensuring that we continually evaluate and refine our development/infrastructure standards and processes to create technology that will deliver sustained value to the business
  • You are responsible for maintaining a high performance, high velocity organization, measuring and iterating on processes as we grow and evolve as a business
  • You will be the leader for recruiting, headcount management and planning, career growth, and training for your part of the organization. As necessary, you will manage vendor relationships and participate in the budgeting process
  • As an engineering director you are responsible for the organization’s overall technical competence, guiding and growing that competence in the whole team as necessary via training and hiring
  • You will not be generally expected to write code on a day-to-day basis; however, you should have a strong technical background and spend some of your time researching new technologies and staying abreast of trends in the tech industry
  • You will be expected to help debug and triage critical systems, and should understand the systems you oversee well enough to perform code reviews and help research problems as needed
  • You should contribute to the architecture and design efforts primarily by working with staff engineers to guide our technical design process and serving as the technically-savvy voice that asks business and product questions of the engineers on your teams, ensuring that the code we are writing matches the product and business needs and can scale appropriately as those needs grow
  • Your impact will reach across multiple areas of the technology organization. You are responsible for creating and growing the next generation of leadership and management talent in the organization, helping that talent learn how to balance technical and people leadership and management
  • You are expected to own retention goals in your organization. Additionally you are responsible for strategically balancing immediate and long-term product/business focused work with technical debt and strategic technical development
  • As an Engineering Director you are a strong leader, and set the example for cross-functional collaboration both between technology and other areas of the company, and across divisions of technology
  • The goal of this collaboration is to create both a strategic and tactical tech roadmap that tackles both business needs, efficiencies and revenue as well as fundamental technology innovation
  • You will help to create a positive public presence for HopSkipDrive tech and are capable of selling the company and their area to potential candidates
  • Due to your breadth of exposure to both technology and the business drivers, you are responsible for guiding the quarterly planning process for all of the teams in your organization, helping these teams articulate goals that support both business initiatives and technology and organizational quality
  • Oversee 3-6 engineering teams, with the managers of those teams reporting to you
  • Own the operational excellence of your teams. Empower their managers to build self-organizing teams with support from you
  • Lead the hiring process for individual contributors and managers on your teams. Exhibit high standards when interviewing and evaluating prospective candidates
  • Run Quarterly planning meetings, weekly managers meetings, and other meetings as appropriate
  • Identify areas of strategic technical debt, do the cost/benefit analysis for resolving this debt and communicate suggested timelines for prioritizing this to your team’s managers
  • Work with the Staff engineers to manage a “technical review” process for changes that impact multiple teams
  • Lead teams through critical architectural decisions with a clear understanding of trade-offs
  • Drive engineering teams to use best practices (i.e. documentation, technical reviews, etc) and incorporate standardized HopSkipDrive engineering practices and principles
  • Manage the on-call process and schedule for your teams
  • Foster professional development efforts
  • Develop new management talent within the teams. Coach new managers in weekly 1:1s. Conduct performance reviews
  • Drive a performance-based culture within your teams, ensuring consistent achievement of business and team health KPIs
  • Collaborate with VP of Engineering on technical roadmap

Otta's take

Theo Margolius headshot

Theo Margolius

COO of Otta

HopSkipDrive is an LA-based organization committed to eliminating transportation barriers for children, including those requiring special assistance. The organization was launched by three women who cite their "Mom DNA" as the reason for the success of HopSkipDrive, entwining their innate desire to help their own kids with the goal of making opportunities accessible to all children.

With all CareDrivers requiring a minimum of five years' experience in a caregiving field, HopSkipDrive operates on the principles of empathy, safety, and reliability. This is a smart rule to implement, as not only can they avoid those with inadequate experience, but they also ensure that employees are truly committed to helping children - the very reason the organization was founded. The company makes money by keeping a percentage of the fares it charges (CareDrivers get the rest).

HopSkipDrive collaborates with a number of social agencies and school districts, providing them with effective youth transportation solutions. Although the company is competing with existing transportation providers, such as national services, it continues to grow as a viable and fresh alternative, raising impressive funds and growing its leadership team with new hires. The company's results back up its success as well, saving 160,000 pounds of CO2 emissions in eight months after launching its SmartPooling ride-share product. Results and moves like these will allow it to expand its services and continue the modernization of school transportation.


Led by a woman
Top investors

Few candidates hear
back within 2 weeks

23% employee growth in 12 months


Funding (last 2 of 7 rounds)

Sep 2022



Aug 2021



Total funding: $107m

Company benefits

  • 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, vision and life insurance, 401(k), and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential

Company values

  • Safety is everything: We leave no stone unturned, we think of every possibility, and we do all that we can to protect the children and CareDrivers at the heart of HopSkipDrive
  • Feel it: Empathy is the essence of our business. We are courageous enough to feel the fears, the stress, the worry of others and we show up to empower and help them so we can share in celebrating their joys, their laughs, and their successes
  • Own it: We are trustworthy, authentic, and accountable. We don’t just show up, we engage fully and wholeheartedly in all that we do to create opportunities for the kids, families, schools, and CareDrivers. We are here for our team and our partners
  • Make tomorrow better: We challenge assumptions and the status quo to achieve continuous innovation. We are curious and believe in being part of the solution instead of dwelling on problems. We move forward, break down barriers, and innovate to make tomorrow better than today - for ALL
  • Drive: We feel an urgency to create opportunity for all, so we move fast and stay nimble while creating solutions and building for scale. We embrace flexibility and efficiency while acting boldly
  • Empower community: We empower the communities we serve by celebrating diversity and being an inclusive team. We embrace different perspectives and experiences because they make us stronger, smarter, and better

Company HQ

Fashion District, Los Angeles, CA


Joanna McFarland

(CEO & Co-founder)

Former Board Member at the Marketplace Industry Association and LA

Janelle McGlothlin


Principal at WriteBand Studio. BA and BSc in International Relations and Strategic Management at University of Pennsylvania.

Co-founder & current CEO at Pearline Health. Former Limited Partner at The Fund.

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