Head of Sales

📋 Description

• • As the Head of Sales at Hauler Hero, you will be at the forefront of modernizing the waste hauling industry, a sector ripe for technological advancement and currently generating a substantial $90 billion in annual revenue across the US and Canada. Hauler Hero provides a cutting-edge vertical SaaS platform designed to streamline operations for waste haulers, replacing outdated legacy software and manual spreadsheet management with a comprehensive operating system. Our platform encompasses critical functions such as dispatch, routing, CRM, billing, accounting, and payments, serving 200 hauling companies and generating $4 million in Annual Recurring Revenue (ARR). This is a unique opportunity to step into a pivotal leadership role, driving significant growth and shaping the future of our revenue engine.
• • This is a hands-on leadership position, demanding a leader who can not only close deals personally but also architect and execute a strategy to build and scale a high-performing sales team. You will be instrumental in defining and owning new logo revenue acquisition, talent acquisition and development, sales process optimization, the implementation of essential sales tooling, and fostering seamless cross-functional alignment with our Marketing and Customer Success departments. Reporting directly to the CEO, this role is envisioned to evolve into broader Go-to-Market (GTM) leadership responsibilities as the company scales.
• • Success in this role is contingent upon your ability to lead by example. A fundamental requirement is the capacity to personally sell the product effectively; if you cannot demonstrate this capability, you will not thrive here. Leading from the front is not just encouraged, it is mandatory. This player-coach mentality is essential for setting the standard and inspiring the team.
• • Understanding the Go-to-Market context is crucial. Our primary buyer personas include Office Managers, Operations Managers, Owners, and Controllers within waste hauling companies. Deals are typically multi-stakeholder and require building consensus across various decision-makers. While most deals are closed remotely, in-person relationship building is expected for larger, strategic wins. Our priority segments are SMB haulers (operating 5-100 trucks) with an Annual Contract Value (ACV) ranging from $15,000 to $250,000, as well as municipal haulers. We also target very small haulers (1-4 trucks) with a smaller ACV of $4,000 to $15,000.
• • You will be joining a dynamic sales environment. The current sales organization comprises an Inside Sales Manager, 2 Sales Development Representatives (SDRs), 4 Account Executives (AEs), and 1 Sales Engineer. Significant planned growth will see the team expand to 11-12 members within the next 3-6 months. Our core sales tooling includes HubSpot for CRM, Grain for call intelligence, and we are actively exploring emerging AI-based workflows to enhance efficiency and effectiveness.
• • Your responsibilities will span both individual contribution and team leadership. As a **Player**, you will conduct product demonstrations, own the entire sales cycle from lead generation to closing, and personally close meaningful ARR deals. You will set the benchmark for excellence in discovery calls, product presentations, and negotiation strategies. As a **Coach & Builder**, you will be responsible for recruiting, hiring, and onboarding top sales talent. You will train representatives to achieve mastery of our product and sales process, manage performance through clear expectations and metrics, and scale a team of high-performing closers.
• • As an **Operator**, you will build robust sales processes and establish a consistent operating cadence. You will own accurate forecasting, proactive pipeline management, and detailed reporting. Crucially, you will partner closely with the Marketing team to refine our Ideal Customer Profile (ICP), messaging, and demand generation strategies. You will also be tasked with implementing modern sales tooling and automation to drive efficiency and scalability.
• • Success will be measured across several key milestones. Within your **First 90 Days**, you are expected to personally close initial new ARR deals, conduct a thorough assessment of the current team's strengths and areas for development, propose a strategic hiring and capacity plan, and implement a consistent pipeline and forecasting cadence. By **6 Months**, the team should be consistently hitting monthly new ARR targets, new hires should be onboarded and contributing effectively, and clear, reliable forecasting should be in place. By **12 Months**, the revenue motion should be operating predictably, the sales team should be scaled to support the next phase of growth, and a proven, repeatable GTM playbook should be established.
• • We are seeking individuals with proven experience scaling SaaS sales from an early stage, a demonstrable track record of personally closing complex deals, and significant experience in hiring and developing high-performing sales teams. Strong operational discipline, a knack for accurate forecasting, and comfort operating in ambiguity while building processes from the ground up are essential qualities we value.
• • This is an unparalleled opportunity to own and build the entire revenue engine of a category-defining product in an overlooked yet critical industry. You will work in direct partnership with the founders and have the chance to shape the GTM strategy from its foundational stages. Join us and make a significant impact on Hauler Hero's trajectory.