Head of Sales

ABOUT HAULER HERO Hauler Hero is a vertical SaaS platform modernizing the waste hauling industry. Hauling generates $90B+ in annual revenue in the US and Canada, yet most operators still rely on legacy software and spreadsheets. We deliver a modern operating system for haulers covering dispatch, routing, CRM, billing, accounting, and payments. Today we serve 200+ hauling companies and generate $4M+ in ARR, with a product built specifically for the operational and financial realities of this industry. THE ROLE We are hiring a Head of Sales to personally sell, build, and scale our revenue engine. This is a hands-on leadership role for someone who can close deals themselves, then turn that motion into a repeatable, high-performing team. You will own new logo revenue, hiring, sales process, tooling, and cross-functional alignment with Marketing and Customer Success. This role reports directly to the CEO and is expected to grow into broader GTM leadership over time. If you cannot sell the product yourself, you will not succeed in this role. Leading from the front is mandatory. GO-TO-MARKET CONTEXT - Primary buyer personas: Office Managers, Operations Managers, Owners, Controllers - Deals are multi-stakeholder and consensus-driven - Most deals close remotely, with in-person relationship building for larger wins - Priority segments: - SMB haulers (5–100 trucks) with $15K–$250K ACV - Municipal haulers - Very small haulers (1–4 trucks) with $4K–$15K ACV CURRENT TEAM & TOOLS - Current sales org: - Inside Sales Manager - 2 SDRs - 4 Account Executives - 1 Sales Engineer - Planned growth to 11–12 team members over the next 3–6 months - Core tooling: HubSpot, Grain, and emerging AI-based workflows WHAT YOU’LL DO PLAYER - Run demos and own full sales cycles - Personally close meaningful ARR deals - Set the standard for discovery, demo, and negotiation COACH & BUILDER - Recruit, hire, and onboard top sales talent - Train reps to mastery - Manage performance with clear expectations - Scale a team of high-performing closers OPERATOR - Build sales processes and operating cadence - Own forecasting, pipeline management, and reporting - Partner with Marketing on ICP, messaging, and demand generation - Implement modern tooling and automation WHAT SUCCESS LOOKS LIKE FIRST 90 DAYS - Personally close initial new ARR deals - Assess current team strengths and gaps - Propose hiring and capacity plan - Implement consistent pipeline and forecast cadence BY 6 MONTHS - Team consistently hitting monthly new ARR targets - New hires ramped and contributing - Clear, reliable forecasting in place BY 12 MONTHS - Revenue motion operating predictably - Sales team scaled to support next growth phase - Proven repeatable GTM playbook WHAT WE’RE LOOKING FOR - Proven experience scaling SaaS sales from early stage - Track record of personally closing complex deals - Experience hiring and developing high-performing sales teams - Strong operational and forecasting discipline - Comfort operating in ambiguity and building from zero WHY JOIN - Own and build the entire revenue engine - Category-defining product in an overlooked industry - Direct partnership with founders - Opportunity to shape GTM from the ground up