Head of Sales

Head Of Sales

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.

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.

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 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

Run demos and own full sales cycles

Personally close meaningful ARR deals

Set the standard for discovery, demo, and negotiation

Recruit, hire, and onboard top sales talent

Train reps to mastery

Manage performance with clear expectations

Scale a team of high-performing closers

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

Personally close initial new ARR deals

Assess current team strengths and gaps

Propose hiring and capacity plan

Implement consistent pipeline and forecast cadence

Team consistently hitting monthly new ARR targets

New hires ramped and contributing

Clear, reliable forecasting in place

Revenue motion operating predictably

Sales team scaled to support next growth phase

Proven repeatable GTM playbook

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

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