Head of Marketing

About Self Inspection

Self Inspection is a cutting-edge technology company revolutionizing vehicle inspections by integrating artificial intelligence, mobile-friendly data capture, and expert validation. This approach provides fast, precise, and transparent information regarding vehicle condition, aimed at simplifying the inspection process. The platform empowers customers to generate reliable, verifiable records that streamline operations and build confidence throughout the vehicle lifecycle.

Position Overview

We are seeking a dynamic and committed Head of Marketing to spearhead and develop our marketing operations during an important phase of expansion. This role requires a leader who is not only strategic but also hands-on, experienced with AI applications, and capable of introducing a new category definition, enhancing our market positioning, stimulating enterprise demand, and constructing a measurable sales pipeline from scratch. You will collaborate closely with company founders, sales, product, and customer success teams to establish Self Inspection as the frontrunner in Vehicle Condition Intelligence.

Key Responsibilities

• Craft and implement comprehensive marketing strategies covering demand generation, product marketing, content creation, branding, communications, event organization, and customer engagement.
• Refine and articulate our category position, value proposition, messaging, and competitive advantages.
• Construct a reliable enterprise demand-generation system that produces qualified leads and drives revenue growth.
• Create account-based marketing initiatives focusing on automotive sectors including lenders, dealers, fleets, rental agencies, mobility companies, and other targeted enterprises.
• Translate sophisticated AI and vehicle intelligence features into clear, actionable benefits for both executive and operational buyers.
• Produce impactful content such as thought leadership articles, customer success narratives, research pieces, sales collateral, presentations, videos, and executive messaging.
• Manage and optimize the company's website, digital footprint, organic reach, paid campaigns, and conversion rates.
• Develop product marketing functions encompassing market research, buyer insights, competitive analysis, product launches, and sales enablement.
• Lead customer marketing strategies to enhance advocacy, references, case studies, expansion, and reputation within the industry.
• Organize and execute industry events such as conferences, webinars, executive panels, and focused campaigns.
• Oversee relationships with external agencies, contractors, technology partners while maintaining direct involvement in execution.
• Implement and continually improve AI-driven marketing processes and modern marketing technology tools.
• Establish marketing performance dashboards, attribution models, KPIs, budget management, and reporting frameworks linking activities to pipeline and revenue.
• Recruit, mentor, and grow a high-performing marketing team aligned with the company's growth trajectory.

Required Skills and Experience

• Proven builder experienced in creating marketing departments from inception.
• Comfortable balancing strategic planning with hands-on execution including copywriting, campaign construction, performance analysis, and initiative launches.
• Experience marketing complex enterprise SaaS products with extended, multi-stakeholder sales cycles.
• Strong technical aptitude with enthusiasm for leveraging AI to enhance research, content development, personalization, campaign performance, and productivity.
• Exceptional storytelling ability to simplify complex technology and relate it compellingly to business challenges.
• Customer-focused mindset with the ability to understand needs of executive, operational, and technical audiences.
• Data-driven approach emphasizing measurable business outcomes over mere activity.
• Ability to perform effectively in a fast-paced, ambiguous, resource-limited, early-stage venture-backed environment.
• Collaborative and influential, able to engage cross-functional teams and external partners.
• Leadership style involving direct participation and development of scalable team structures and processes.

Minimum Qualifications

• 8 to 12+ years in B2B marketing, including substantial experience with enterprise SaaS.
• Track record leading marketing in startups or fast-scaling companies.
• Demonstrated expertise in building marketing strategy and operational cadence from scratch.
• Proven ability to generate qualified pipeline and link marketing investments to revenue results.
• Strong background in product marketing, including positioning, messaging, category development, and sales enablement.
• Experience designing account-based marketing and demand generation programs targeting complex enterprise buyers.
• Deep understanding of enterprise sales cycles, purchasing committees, and executive decision processes.
• Excellent communication skills across written, verbal, editorial, and presentation formats.
• Familiarity with marketing automation and CRM platforms like HubSpot, analytics tools, paid media, content management systems, and AI-powered marketing technologies.
• Experience managing third-party agencies, contractors, budgets, and cross-functional marketing projects.

Preferred Qualifications

• Marketing experience in AI, data, workflow, or specialized vertical SaaS products.
• Exposure to the automotive industry.

Why Join Us?

• Opportunity to define and lead marketing in a groundbreaking technology category.
• Chance to shape marketing function and brand during a crucial growth phase.
• Work with a rapidly expanding company supported by major Silicon Valley investors and automotive industry leaders.
• Engage with top North American automotive customers.
• Collaborate directly with founders and executive leadership.
• Participate in Board meetings and influence strategic company plans by presenting marketing performance and growth strategies.
• Help innovate how AI reshapes vehicle inspections and automotive industry decision-making.

Additional Information

Location is remote but candidates must align with North American business hours for regular overlap. Due to high application volumes, only shortlisted candidates will be contacted within two weeks.