Senior Sales Enablement Manager

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

We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions. As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what’s possible in mobility, while making a meaningful difference for those who need it most.

About the Role

You are a strategic and results-oriented sales enablement professional, passionate about empowering sales teams to achieve their full potential. You possess a strong understanding of the sales lifecycle and a proven track record of designing, implementing, and optimizing enablement programs that contribute to revenue growth. You are a proactive problem-solver who collaborates effectively across functions to identify opportunities, develop practical solutions, and champion the adoption of best practices and relevant technologies. You are capable of both strategic planning and hands-on execution, committed to fostering continuous improvement and excellence within the sales organization.

Responsibilities

• Oversee the assessment and identification of sales efficiency gaps and opportunities for improvement across the sales lifecycle.
• Drive the implementation of a comprehensive sales enablement strategy, partnering closely with sales leadership, marketing, and product teams to ensure alignment with organizational goals and revenue objectives.
• You will report directly to the Director of Marketing, while working very closely with sales leadership, and will be responsible for managing and mentoring junior enablement team members.
• Design and execute impactful, data-driven solutions that elevate the sales process, optimize workflows, and maximize productivity for sales teams.
• Develop and deliver advanced training curricula and coaching sessions for the sales team, covering sales methodologies, product and market knowledge, objection handling, negotiation strategies, and sales skills.
• Manage the creation and curation of comprehensive, high-impact sales enablement content, including presentations, e-learning modules, video series, sales playbooks, and sales scripts, ensuring accessibility and effectiveness.
• Establish and maintain a centralized sales knowledge repository, incorporating competitor analysis, industry trends, and sales collateral.
• Lead the design and execution of new hire onboarding programs, providing continuous support and mentorship to accelerate sales team ramp-up and foster professional development.
• Collaborate effectively with marketing, product, and communications teams to generate compelling sales enablement collateral, such as case studies, sales decks, and product presentations.
• Partner with Sales Leadership to select and implement a sales methodology for the Account Executive and Account Manager teams.
• Continuously evaluate, refine, and iterate on sales training programs based on performance metrics.