Director Of Strategic Initiatives

Who we are
HopSkipDrive 's mission is to create opportunity for all through mobility. Our innovative, supplemental school transportation solutions are used by over 400 school districts, charter schools, nonprofits, government agencies, as well as busy families to safely and reliably get kids where they need to go.
Student transportation is the largest mass transit system in the U.S. The way kids get to and from school has a direct impact on our kids, families, schools and communities. While school districts spend $28 billion annually on transportation, only 30% of kids get to school on a bus. The current system can no longer meet all the transportation needs of our districts, schools and families - and its shortcomings are causing inequities in educational access that are affecting the welfare of millions of kids each day.
HopSkipDrive is taking a different approach to arranging safe, reliable school transportation that meets needs that aren't being addressed by the current system, helping to fill gaps and supplement the student transportation options available. We create personalized transportation solutions for the one to the many, and everything in between.
We're a company with heartOur partnerships with school districts, child welfare agencies and nonprofits ensure equitable educational access for the most vulnerable populations, including youth in foster care, children experiencing homelessness and students with disabilities.
We understand that the difference between struggle and success can sometimes be as simple as the ability to show up, which is why we're on a mission to use innovative technology - coupled with operational expertise and new ways of thinking - to help kids reach their full potential by providing a safe, dependable way to get them where they are going.
We're an awesome place to workOur company culture has been well-recognized - HopSkipDrive has been named to Fast Company's Most Innovative Companies list, as well as Best Places to Work lists from Built In LA, Comparably, Inc., and the Los Angeles Business Journal. Comparably also named us a Best Company for Professional Development, as well as to its Best CEO and Best CEOs for Women lists.
We're growing rapidlyFounded by three moms as a solution to their own transportation challenges, we now operate across over 20 major markets and more than a dozen 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 has raised $100M in funding to date.
You are looking for a challenging and rewarding experience. You are inspired by our vision and the opportunity to define a new category in an incredibly fast-growing market. You are excited to learn, grow and collaborate so we can achieve our mission of creating opportunity for all through mobility.
You are equally comfortable with thoughtful deliberation for strategy development as well as scrappy execution for early validation and proof points. You are comfortable with developing objective, data-driven, merit-based perspectives and then aligning the rest of the organization accordingly.
You are a collaborative team player with strong influence and executive presence. You are analytical, detail-oriented, organized and have a passion for making things happen. You are excited about bringing calm to chaos and are comfortable both leading and contributing to projects. You are comfortable juggling multiple high impact priorities and thrive in ambiguity.
Above all, you want to build something that fundamentally changes the lives of families for the better.
What you'll do:

• Partner with leadership on key Strategic Initiatives from concept to reality with a broad impact on company outcomes
• Evaluate opportunities and influence strategy by building detailed business cases for key initiatives
• Revamp and continuously improve overall project architecture (inflow, reporting, risk evaluation, retrospectives etc.)
• Manage and mentor a team of project managers and operators

What you'll bring

• 6+ years of experience in business operations, strategy and project management at a fast-paced tech startup or equivalent experience in consulting or investment banking
• Able to take broad strategy, break it into a clear roadmap and manage the cross-functional execution.
• Relentless focus on execution that goes beyond analysis and strategy.
• Advanced Excel and Powerpoint skills. You are highly analytical and live in the data. You can operate at a 50K foot level, a 5K foot level, and in the blades of grass.
• Able to develop strategy, build a case and tell a persuasive story to drive decision making and buy-in across an organization.
• Demonstrated project management skills and ability to work across functions. You can motivate others without direct reporting lines.
• Advanced knowledge of project management software (ClickUp, Asana, Jira)
• Self starter. You can own complex projects with minimal input.
• Team player with excellent interpersonal skills. You have high EQ and can readily develop trust and credibility across all levels.
• Excellent communication skills. You can tell a written story, convert it into a visual story in powerpoint, and speak it to both big and small rooms.
• You can give and receive candid feedback.
• Strong executive presence. Able to interact effectively with C-level audiences.
• You have intense curiosity and a drive to make things better.
• Bachelor's degree required, MBA preferred

** This role will be fully remote from a state where we do business AZ, CA, CO, FL, IL, KS, MD, MI, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**
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 flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, 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 $130,000- $150,000. This compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate's relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
Equal Opportunity Employer
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. HopSkipDrive is also proud to operate as a drug-free workplace.