Head of Marketing

Job Description

Job Description

Position Summary:

Prestige Trucking Insurance is seeking a hands-on Head of Marketing to build and grow our marketing department from scratch. This is a builder's role for a marketer with deep, proven expertise who knows the craft inside and out. The person we hire will establish the procedures, workflows, systems, and standards the function runs on, and in the early stage will personally produce the work, writing the copy, designing the creative, shooting and editing the video, launching the campaigns, and building the automations that move the business forward. As the department's needs grow, this individual will hire the right people around the foundation they have built, shaping the team to fit the systems and standards already in place. Throughout, they use automation and AI to strengthen and scale their work rather than replace their own judgment, understanding and owning every output as their own. This role reports directly to a key senior executive and supports marketing and growth across Prestige Trucking Insurance and its related companies, including online lead generation, brand building, and multi-channel business development, while keeping every initiative compliant with the rules and regulations of all applicable regulatory bodies.

This is a unique opportunity to make your mark and take ownership of a key facet of growth for a rapidly growing conglomerate. This is a role for someone who wants to challenge assumptions, drive data driven solutions, and build something truly special. You bring genuine, hands-on expertise and use automation and AI to strengthen and scale your work, not to do it for you. You understand the output, own the quality, and stand behind the work. This is a rare opportunity to build a marketing department from the ground up and own the results directly. This is not just a job but an opportunity to do something truly innovative for a group of companies disrupting their space.

Essential Duties and Responsibilities:

Hands-On Execution

• Personally plan, create, and publish marketing content across all channels, including written copy, graphics, photography, and video.

• Design and produce creative assets end to end using the Adobe Creative Suite, including Photoshop, Illustrator, Premiere Pro, and related tools.
• Shoot, edit, and produce photo and video content for social media, advertising, and the company website.
• Build, launch, and manage paid advertising on Meta (Facebook and Instagram) and Google Ads, including audience targeting, creative, budgets, and ongoing optimization.
• Run the organic social media presence day to day across all platforms, including the content calendar, posting, and community engagement.
• Plan, write, build, and send email marketing campaigns, including audience segmentation, sequencing, deliverability management, and performance tracking.
• Execute digital strategies across AEO, SEO, SEM, social media, and local listing management to increase high-intent traffic.
• Build custom marketing automations and workflows from the ground up, not tied to any single CRM or off-the-shelf platform, to reduce manual effort and let a lean team operate like a larger one.
• Apply automation and AI to strengthen and speed up your own work, bringing professional judgment and quality control to everything produced.

Strategy and Ownership

• Own the end-to-end marketing strategy and be accountable for pipeline generation and revenue contribution.
• Define the company's content, creative, and storytelling direction, then personally produce the work that brings it to life.
• Establish KPIs, track attribution and performance, and use the data to decide where to invest next.
• Leverage data, analytics, and market insight optimize marketing investments and demonstrate measurable ROI tied to growth objectives.
• Put standards, systems, and automations in place now that a future team can scale on, so growth comes from better process rather than simply adding head count.
• Partner with the CEO and leadership to align marketing and brand standards with the company's mission, vision, and strategic plan.

Building the Function From the Ground Up:

• Define the procedures, workflows, systems, and standards the function runs on, and in the early stage you will personally produce the work rather than directing others to do it.
• Own the metrics for the department's growth plan and hire the right people around the systems, standards, automations, and workflows you have established, shaping the team to fit the foundation you built.

General Marketing Compliance

• Ensure all marketing initiatives comply with applicable federal, state, and industry regulations, as well as company policies and brand standards.
• Ensure all marketing materials, advertising campaigns, and digital content comply with insurance regulations, carrier guidelines, state advertising requirements, and company branding standards, while partnering with Compliance and Executive Leadership to mitigate risk.

Knowledge, Skills, and Abilities (KSA's):

• Hands-On Craft and Production: Personally produces high-quality marketing work across disciplines, including copywriting, graphic design, photography, video production, and campaign execution, rather than relying on others or on automated tools to produce it for them.
• Technical and Platform Proficiency: Fluent in the Adobe Creative Suite, Meta Ads Manager, Google Ads, email marketing platforms, social media management platforms, and the automation and AI tools used to strengthen and scale marketing work.
• Custom Automation and Systems Building: Designs and builds custom marketing automations and workflows that are not tied to a single CRM or platform, connecting tools and data to streamline execution and scale output.
• Strategic and Operational Judgment :Brings the perspective of a seasoned leader who can set direction, prioritize effectively, and build the systems and structure a marketing function needs to scale.
• Analytical and Problem-Solving Skills: Establishes KPIs, analyzes attribution and performance metrics, identifies market opportunities, and develops data-driven solutions that optimize marketing investments and demonstrate measurable ROI.
• Legal, Business, and Financial Acumen: Possesses a strong understanding of business operations, financial principles, regulatory compliance, and marketing law, enabling sound, brand-aligned decisions across all applicable regulatory bodies.

• Self-Direction and Ownership:Operateswith minimal oversight, sets priorities independently, and takes full accountability for outcomes in an environment where they are the marketing function.
• Integrity and Accountability:Consistentlydemonstratesa high levelof professional integrity, ethical conduct, and personal accountability in all marketing decisions, vendor relationships, and leadership responsibilities.
• Confidentiality Knowledge and Practice:Maintainsthe highest degree of confidentiality when handling sensitive company strategy, proprietary marketing data, vendor agreements, and executive-level communications.
• Organizational and Time Management Skills:Capable of managing multiple complex marketing projects simultaneously with minimal guidance, meeting tight deadlines, andmaintainingaccuracy and prioritization across all channels and campaigns.

Minimum Qualifications:

Required:

• 8 to 12 years of progressive marketing experience, including time spent leading or managing marketing teams or functions.
• A hands-on operator who wants to personally execute the work, not only oversee or delegate it, and who brings the judgment of someone who has already led and managed.
• A portfolio of work the candidate personally created across design, content, video, and campaigns.
• Demonstratedproficiencywith the Adobe Creative Suite, such as Photoshop, Illustrator, and Premiere Pro or equivalents.
• Proven experience building and managing paid campaigns in Meta Ads Manager and Google Ads.
• Provenproficiencyplanning and executing email marketing campaigns, including segmentation, deliverability, and performance measurement.
• Hands-on experience producing photography and video content for marketing use.
• Direct experience managing organic social media across the major platforms.
• Experience building custom marketing automations and workflows, not limited to a single CRM, and using automation and AI to strengthen and scale output.
• Bachelor's degree in Marketingor a related field.
• Strong leadership, mentoring, and organizational skills.

• Highly analytical with a strong understanding of attribution and performance metrics.
• B2B and B2C experience in services or solution-selling environments.

Preferred:

• Energized by building something from the ground up and being hands-on during the early phase, while looking forward toestablishingand leading a team as the department grows.
• Experience building marketing from 0 to 1 in fast-paced companies or start-up environments.
• A strongtrack recordof automating the marketing process and scaling output without simply growing head count.
• Experience in insurance operations, preferably on the agency or Insurtech side.
• Experience infranchising operations.

• 15+ years of progressive marketing experience.
• Master's degree in Marketingora relatedfield.

Physical Demands and Work Environment:

• Requires extended periods of sitting, computer use, and handling digital documents, along with clear communication via phone and video.
• Involves hands-on content production, which may include operating cameras and related equipment and occasionally appearing oncamera.
• Professional office worksettingwith standard office equipment and moderate noise levels.
• Fast-paced environment with occasional extended hours during campaign launches or operational rollouts.
• Limited travelrequiredfor vendor, carrier, content, or regulatory meetings.
• Requires handling confidential company strategy, marketing data, and organizational information in compliance with privacy and legal standards.