VP of Sales

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 sales team is dedicated to fostering strong, ongoing relationships with HopSkipDrive clients. We focus on growing existing partnerships, driving increased usage, and identifying opportunities to expand services and meet evolving client needs. Our primary goal is to maximize value and volume for our clients and HopSkipDrive.

Who You Are

We are seeking a seasoned, results-oriented sales leader with significant experience in B2B account management: upselling and renewals, inclusive of nurturing existing relationships as well as net new expansion within existing accounts. You will be responsible for leading and refining our account management strategy, building numerous supporting processes, philosophies, and playbooks from the ground up. You will oversee the team that manages and identifies new revenue opportunities within our existing customer relationships, and will support the business in the following ways:

• Strategic Account Growth: Develop, roll out, and support the Account Management team in implementing new, comprehensive account growth strategies to maximize revenue and volume from existing client relationships. Identify and capitalize on opportunities for upselling, cross-selling, and expanding product/service adoption.
• Team Leadership & Development: Lead, mentor, and motivate a high-performing team of Regional Sales Managers and their Account Manager reports. Provide ongoing coaching, performance feedback, and professional development opportunities to ensure individual and team success.
• Performance Management: Establish clear KPIs and sales targets, with associated sales methodologies and process expectations, for the account management team. Monitor performance, analyze sales data, and implement corrective actions as needed to ensure goals are met or exceeded.
• Client Relationship Management: Oversee the cultivation and maintenance of strong, long-term relationships with key clients. Act as an executive sponsor for critical accounts, ensuring high levels of client satisfaction and loyalty.
• Process Optimization: Continuously evaluate and refine account management processes, tools, and methodologies to enhance efficiency, effectiveness, and scalability.
• Collaboration & Cross-Functional Alignment: Work closely with marketing, product development, customer success, and operations teams to ensure a seamless client experience and to align sales strategies with overall business objectives. Empower Regional Sales Managers and Account Managers to drive cross-functional decision making of their own.
• Market Insights: Stay abreast of industry trends, competitive landscape, and client needs to inform sales strategies and new growth avenues.
• Reporting & Forecasting: Partner closely with revenue operations and sales managers to provide accurate sales forecasts, pipeline reports, and performance analyses to senior leadership.

What You Bring:

• 10+ years of sales experience within the software or SaaS industry, preferably within education/youth advocacy, edtech, and/or transportation
• 5+ years in a sales leadership role, managing people managers and an overall team of 30+ individuals
• 5+ years experience in upselling and renewals: nurturing existing client relationships as well actioning net new revenue opportunities within existing accounts
• Proven track record of developing, actioning, and tracking effectiveness of processes resulting in exceeded sales targets and notable revenue growth
• Proficiency in – and demonstrated experience enabling a team to learn and apply – diverse sales and training methodologies
• Experience managing, coaching and developing  high-performing teams
• Excellent analytical skills, with the ability to leverage data to inform decisions and drive results
• Strong understanding of, and experience running, a usage-based sales process, including lead generation and outbound prospecting, pipeline management, closing strategies, and client engagement and relationship management with sell-through processes to drive volume usage
• Experience with CRM tools and sales analytics platforms, preferably including Salesforce, Seismic, and Outreach
• Experience building trust, credibility, and collaboration with both internal and external audiences through clear and effective communication
• A startup mentality, with the ability to work independently in a fast-paced, deadline-driven environment with minimal direction and high visibility

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 committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is expected to be between $175,000 - $200,000/year with an expected On Target Earnings (OTE) of $400,000/year (including bonus or sales incentive). 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, CT, 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**