Engineering Director

| Remote
Employer Provided Salary: 200,000-220,000 Annually
Salary data is provided by the employer. Please note this is not a guarantee of compensation.
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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 facilitated 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 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 should be obsessed with creating high-functioning, engaged and motivated organizations, and 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 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. 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.

What you will do:

  • 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

What you'll bring:

  • 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.

Our Investment In You

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 $200,000 to $220,000 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**

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Technology we use

  • Engineering
  • Sales & Marketing
    • GolangLanguages
    • JavaLanguages
    • JavascriptLanguages
    • RubyLanguages
    • SqlLanguages
    • SwiftLanguages
    • jQueryLibraries
    • ReactLibraries
    • Ember.jsFrameworks
    • Ruby on RailsFrameworks
    • MemcachedDatabases
    • PostgreSQLDatabases
    • RedisDatabases
    • SalesforceCRM


HopSkipDrive HQ officially moved to a new office this week in the Little Tokyo district in Downtown LA! Can't wait to see what adventures lie ahead.

An Insider's view of HopSkipDrive

What’s the vibe like in the office?

HopSkipDrive has the best office vibe I’ve experienced, and that’s all thanks to my coworkers. My favorite moments of the day are the small, unexpected conversations I get to have– in the kitchen grabbing coffee, in the elevator, or passing in the hall. I look forward to coming into work because of them. Well, them and our many good office dogs

Emily Durrett

Office Administrator

What are some things you learned at the company?

I learned to identify my strengths and interests in a work environment. Rather than chasing promotions, I learned to look for the work I I’d like to do. Startups make this easier because there are so many opportunities to move, change, and grow.

Mira Hayashi

CX Training Manager

How do your team's ideas influence the company's direction?

We make it a priority at HopSkipDrive to foster a trusting and collaborative culture which improves and enhances our ideas and strategies on a daily basis. This has allowed us to successfully bring to market a service that challenges the status quo as it relates to connecting access to transportation with educational outcomes.

Toby McGraw

SVP of Sales

How does the company support your career growth?

I look forward to going in to work, a work environment that pushes me to improve, that gives me the support and structure to grow into a better thinker, braver woman, all the while still letting me be the quirky clown that I am.

Leora Juster

Software Engineer

What are HopSkipDrive Perks + Benefits

HopSkipDrive Benefits Overview

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity in the company. We offer competitive market comp, onsite state of the art gym membership, BYOD technology reimbursement, unlimited vacation, FSA, medical, dental and vision, 401(k), weekly catered lunches, and an opportunity to work for a uniquely positioned, VC-backed company in a space with significant upside potential.

Partners with nonprofits
Open door policy
OKR operational model
Team based strategic planning
Pair programming
Open office floor plan
Flexible work schedule
Remote work program
Our remote work program includes full-time remote for specific positions, and the ability to work remotely on occasion for all positions.
Highly diverse management team
Mandated unconscious bias training
Hiring practices that promote diversity
Health Insurance + Wellness
Flexible Spending Account (FSA)
Disability insurance
Dental insurance
Vision insurance
Health insurance
Life insurance
Team workouts
HopSkipDrive employees work out together at the free onsite gym.
Financial & Retirement
Company equity
Child Care & Parental Leave
Generous parental leave
Family medical leave
Company sponsored family events
HopSkipDrive hosts our annual summer party with the Company and their families.
Vacation + Time Off
Unlimited vacation policy
Paid holidays
Paid sick days
Office Perks
Commuter benefits
HopSkipDrive offers a reimbursement program for using public transportation to get to work; in addition to a pre-tax commuter benefits for all employees.
Free snacks and drinks
Company-sponsored happy hours
Happy hours are hosted at all the amazing nearby downtown LA spots.
Onsite office parking
Pet friendly
HopSkipDrive's pet policy is dog friendly.
Onsite gym
Professional Development
Job training & conferences
HopSkipDrive offers employees professional development opportunities like annual individual budget for training, The ability to attend job related conferences and seminars.
Lunch and learns
HopSkipDrive hosts weekly lunch and learns.
Promote from within

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