Head of Sales

About Self Inspection

Self Inspection is a technology firm revolutionizing vehicle inspections by integrating AI, mobile-first data capture, and expert validation. Their platform ensures swift, accurate, and transparent vehicle condition information, creating dependable and verifiable records that optimize operations and enhance confidence throughout a vehicle's lifecycle.

Role Overview

We are searching for an outstanding Head of Sales to architect, lead, and drive our commercial growth strategy. This role is unique, blending technical expertise with hands-on leadership, aimed at generating new business and coaching the sales team. The ideal candidate thrives in constructing effective pipeline, pursuing new business opportunities, and refining outbound sales methodologies.

Key Responsibilities

• Independently generate and close new business through targeted outbound prospecting.
• Manage a personal sales pipeline while mentoring the wider sales team to develop theirs.
• Lead and grow inside sales representatives across North America.
• Oversee the demand generation agency to ensure marketing contributes to qualified lead pipelines.
• Continuously design and enhance outbound sales playbooks, messaging, outreach sequences, and processes.
• Conduct weekly pipeline reviews, forecasting, and manage revenue delivery.
• Increase conversion rates at every stage of the sales funnel.
• Implement and optimize AI-driven sales workflows and modern go-to-market technologies to boost team productivity.
• Master platforms like Apollo, Gong, HubSpot, LinkedIn Sales Navigator, ChatGPT, and other emerging AI sales tools.
• Create dashboards, KPIs, and reporting systems that foster accountability and sustainable growth.
• Collaborate with Customer Success, Product, and Marketing teams to drive customer acquisition and expansion.
• Recruit, mentor, and develop upcoming sales talent.

Required Qualifications and Experience

• 6 to 10+ years of experience in B2B SaaS sales with a proven history of consistently exceeding sales quotas through outbound efforts.
• Experience leading teams such as SDRs, inside sales, or account executives.
• Strong expertise in building outbound sales strategies from scratch.
• Deep knowledge of modern sales technologies including CRM, sales engagement platforms, conversation intelligence, and AI-powered go-to-market tools.
• Proven ability to leverage AI to enhance prospecting, research, outreach, productivity, and customer interactions.
• Experience managing partnerships with external demand generation or marketing agencies.
• Excellent written, verbal, and presentation communication skills.
• Highly technical, AI-native, and data-driven with a passion for continuous improvement.
• Demonstrated ability as a player-coach who leads by example and a strong hunter mentality for new business development.
• Ability to operate effectively in a dynamic, fast-paced, venture-backed startup environment.
• Curious, resourceful, and energized by overcoming complex commercial challenges.

Preferred Attributes

• Previous experience in the automotive industry is an advantage.

Why Join Us?

• Opportunity to define and lead a pioneering technology category.
• Join a fast-growing company backed by prominent Silicon Valley venture capital firms and notable automotive industry leaders.
• Engage with some of North America's largest automotive companies.
• Work directly alongside experienced founders and senior leadership.
• Gain involvement in Board of Directors meetings and strategic company planning, presenting business performance and growth initiatives.
• Build a world-class commercial organization while significantly influencing the automotive industry's future.

Additional Information

Location: Remote within USA or Canada.
Employment Type: Full-time.
Level: Senior leadership (Head of Sales).
Due to high application volumes, only selected candidates will be contacted within two weeks of application submission.