VP of Sales

Summary

Join HopSkipDrive's sales team as a seasoned sales leader to spearhead account management, build processes, and mentor a high-performing team. Develop and implement comprehensive account growth strategies to maximize revenue from existing clients. Lead, mentor, and motivate a team of Regional Sales Managers and Account Managers. Establish clear KPIs and sales targets, monitoring performance and implementing corrective actions. Oversee client relationship management, acting as an executive sponsor for critical accounts. Continuously evaluate and refine account management processes for efficiency and scalability. Collaborate with cross-functional teams to ensure a seamless client experience. Stay updated on industry trends and competitive landscapes. Provide accurate sales forecasts and performance analyses to senior leadership.

Requirements

• 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
• 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 usag
• 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

Responsibilities

• 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
• 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
• 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
• 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
• Continuously evaluate and refine account management processes, tools, and methodologies to enhance efficiency, effectiveness, and scalability
• 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
• Stay abreast of industry trends, competitive landscape, and client needs to inform sales strategies and identify new growth avenues
• Partner closely with revenue operations and sales managers to provide accurate sales forecasts, pipeline reports, and performance analyses to senior leadership

Benefits

• Flexible vacation
• Medical, dental, vision and life insurance
• 401(k)
• FSA
• Equity