Head of Sales

More than 26 million students ride 500,000 buses to and from school daily. That operation is managed by under-equipped transportation teams using pen & paper or legacy software, which struggle to solve today’s challenges, including increasing route complexity, overwhelming parent demands, and a severe driver shortage. BusRight is the Student Transportation Operating System; a single platform, purpose-built for school buses, unifying routing optimization and turn-by-turn driver navigation with real-time collaboration and communication tools - to ensure kids get to and from school safely and efficiently.

Role

We’re excited to hire a Head of Sales (New York or Boston-based) following a $7M Series A in 2023, 3x ARR growth YoY, and expansion into 20+ states. As the first Head of Sales, you’ll join BusRight’s executive team, report directly to the CEO, and will be instrumental in executing BusRight’s sales strategy. You’ll lead a sales team of nine, with two Regional Sales Managers (RSMs) and a Head of Revenue Operations reporting directly to you. You’ll also support the success of two Pods, led by RSMs, by providing mentorship, coaching, and strategic direction to achieve ambitious revenue (ARR) targets. 

Responsibilities

• KPI Ownership: Own the outcomes of KPIs across the sales team, such as ARR, CARR, and Pipeline Generated. You’ll be responsible for growing CARR by 2.5x YoY to support continued investments in product and team expansion and ensure BusRight is well-positioned for a strong Series B financing round in the next 24 months. You’ll also lead sales reporting efforts and presentations associated with these KPIs to the company, board of directors, and future investors.

• Coaching: Ensure that top-performing sellers are retained and incentivized to add value to the business long-term. Coach the team on a consistent sales process (e.g., cold call talk tracks, demos, trade show approach, conference presentations, sales collateral, etc.) 

• Culture: This role is more about upskilling BusRighters than running an existing sales playbook that worked at a prior company. The main “playbook” we desire from a Head of Sales is one that focuses on training team members and developing world-class sellers and leaders.

• Forecasting: During weekly forecasts, support closers by examining their pipeline, ensuring healthy pipeline creation, and inspecting deals for forecast judgment and accuracy. You’ll lead weekly forecasts with both RSMs and also participate in weekly forecasting calls between RSMs and ISRs to ask questions, share advice, and ensure consistency across forecasting processes.

• Recruitment: Develop a proactive recruiting strategy, consistently build new relationships, and nurture existing relationships with potential BusRighters.

• Cross-functional Alignment: Collaborate with the customer success, product, and engineering teams to ensure a cohesive approach to customer acquisition, retention, and satisfaction - while advocating to develop high-impact features brought up during the sales process.

What we’re looking for

• Proven track record of success leading a sales team at high-growth companies across multiple stages of growth (e.g. from Series A to Series C+).

• Demonstrated track record of success selling and/or leading outbound sales motions with 2-4 month sales cycles and $20-40k ACVs. 

• Comfortable traveling domestically (US) ~25% of the time for prospect visits and conferences.

• Experience selling into an industry with non-tech-savvy users and empowering champions to sell a solution to their respective leaders and decision-makers.

• Bonus points if you have experience selling vertical software, selling into the government or K12 industry, and/or have participated in at least two venture financing rounds.

• Prior experience leading BDR or related demand generation roles and experience leading senior Account Executives.

• Demonstrated ability to hire, train, and upskill sellers consistently.

• Familiar with using Salesforce, Salesloft, and other modern sales and marketing platforms.

• Excellent public speaking skills and comfortable presenting in front of hundreds of customers and prospects.

What you’ll get

• Competitive Compensation: You’ll receive competitive equity + OTE at a fast-growing startup poised to transform the largest mass transit system in the U.S.

• Resources & Access: You’ll be equipped with industry-leading tools and a network to grow personally and professionally. With investors, advisors, and team members eager to support your personal development, we will ensure you have the opportunity to build relationships with leaders who have built and scaled iconic companies such as Quizlet, HubSpot, & Kayak.

• Strategic Influence: Working side-by-side with BusRight’s CEO and executive team, you’ll be an integral part of critical decisions regarding hiring plans, organizational structure, guiding product development, and more.

We believe that your longevity at BusRight is an asset, and the deepest and most successful relationships are built when our backs are up against a wall. We believe in doing something so kind to fellow BusRighters and customers that it feels like magic. We believe that superficial destinations don’t create daily motivations, rather, the camaraderie we build with each other and the hope we provide our customers are what fuels high performers and high impact. We believe difference is an asset. We're committed to fostering an inclusive environment that welcomes team members of all ages, races, backgrounds, ethnicities, and more. Simply put, our employees, customers, and team win when we have various perspectives and backgrounds at the table making key decisions.