Director, Revenue Operations

About HopSkipDrive

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, 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 five million rides across over 17 states around 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.

Who We Are

Our Revenue Operations team is building the processes and systems to ensure our sales machine runs effectively and efficiently. The Director of Revenue Operations will be critical in identifying areas to drive revenue growth, increase performance visibility, and proactively shaping our go-to-market motions. This person will directly manage a team of Revenue Operations professionals including Salesforce Administration, Sales Operations, and Contract Operations. We, and you will, support the business through the following responsibilities:

• Partner with leadership to develop and align go-to-market strategies, focusing on acquisition, utilization, retention, and growth.
• Lead and optimize go-to-market processes and systems architecture across Sales, Sales Development, Customer Success, and Marketing.
• Identify and work cross-functionally with the teams and subject matter experts who influence revenue success – championing structured problem solving through informed hypotheses, data and effectiveness analyses, and tactical solutioning.
• Drive revenue insights, and performance visibility through robust reporting, ad hoc analytics, and KPI frameworks.
• Oversee and optimize the revenue technology stack, inclusive of Salesforce, ensuring data integrity and effectiveness across all commercial systems (CRM, CSM platforms, support solutions, etc.).
• Define and manage the revenue forecasting process through pipeline management, revenue attribution, process adoption, managing deal reviews, and enforcing data quality.
• Manage and mentor direct reports, including Salesforce Administration, Sales Operations, and Contract Management, fostering a high-performing team.
• Assist in annual and quarterly GTM planning cycles, including headcount planning, comp design, quota setting, and territory creation.

Who You Are

You are a strategic problem-solver with a builder's mindset and a passion for operational scale. You excel at structured problem-solving and can translate insights into actionable strategies in fast-paced, high-growth environments. With the following skills, you'll make a tangible and immediate impact:

• Experience:
  • 3+ years of RevOps experience required
  • 2+ years of management consulting experience preferred
• Skills:
  • A strong background in building and scaling processes, systems, and teams, with the ability to break down complex problems into individual components, formulate hypotheses, and utilize data to drive solutions.
  • Demonstrated ability to define key metrics, develop dashboards, and lead data analysis to provide actionable insights.
  • Proven experience leading high-performing teams, fostering collaboration, and influencing across complex organizational structures.
  • Deep understanding of go-to-market motions, strong familiarity with revenue teams (go-to-market ops, rev ops, sales ops), and experience in developing and aligning GTM strategies including sales, customer success, and marketing operations.
  • Experience supporting sales teams, including building territories, quotas, and compensation plans, and forecasting for different roles.
  • Strong technical understanding of CRM systems (e.g., Salesforce)