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Senior Sales Enablement Manager

Remote - US

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. 

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. You will contribute to this team in the following ways: 

  • 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, sales team feedback, and evolving market dynamics.
  • Analyze sales team performance, identifying areas requiring additional support, skill enhancement, or process optimization.
  • Champion and drive adoption and optimized utilization of critical sales enablement technologies, including CRM systems, sales automation platforms, and content management tools.
  • Stay informed about emerging trends, technologies, and best practices in sales enablement, and proactively introduce new ideas and solutions to the team.

Who You Are

  • 5+ years of progressive experience in sales enablement, sales training, or a similar role within a B2B environment, with a proven track record of contributing to sales performance improvements.
  • Strong understanding and proven experience with sales processes, methodologies, and best practices, with the ability to design and implement effective solutions.
  • Strong communication, presentation, and facilitation skills, with the ability to articulate complex concepts clearly and concisely.
  • Strong analytical and problem-solving abilities to identify sales challenges and design effective, scalable interventions.
  • Proficiency in leveraging and optimizing sales enablement technologies, including CRM systems (e.g., Salesforce), content management systems, and sales automation platforms.
  • Proven ability to build and foster strong, collaborative relationships with cross-functional teams (sales, marketing, product, operations) to drive alignment.
  • Self-motivated, proactive, and independent mindset with the ability to manage multiple projects simultaneously and thrive in a fast-paced, evolving environment. Passion for our mission to create opportunity for all through mobility.
  • High attention to detail, strong organizational skills, and project management capabilities to oversee concurrent initiatives effectively.
  • Solid business acumen with an understanding of market dynamics and the ability to translate insights into actionable sales enablement strategies.

 

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 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 proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The base salary range for this role is $110,000 - $135,000. This position is remote and, as such, 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.

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, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**

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