Job Summary

Portside is hiring a Head of Marketing to build and lead our marketing function from the ground up. This role reports directly to the CEO, with an expectation that reporting will shift to a Chief Revenue Officer once that hire is in place.

Marketing at Portside today consists of three people with a current focus on events and demand generation. This is a build role, not a refinement role: you will design the strategy, systems, and team structure for brand, demand generation, and sales development largely from scratch, while inheriting and improving what already exists.

You'll partner closely with Sales, Product, and Customer Success to establish marketing as a core driver of pipeline and revenue across business aviation, regional airlines, and aircraft leasing & finance. The ideal candidate has built or substantially scaled a marketing function at a small or early-stage B2B SaaS company, is comfortable spanning brand, content, demand generation, and business development, and thrives operating with significant autonomy and limited early infrastructure.

Key Responsibilities

• Serve as Portside's senior-most marketing leader, setting overall marketing strategy and priorities in partnership with the CEO (transitioning to the CRO) and executive team.
• Assess the current state of marketing and build a function from a three-person base, closing gaps in strategy, structure, and execution.
• Hire and build out the marketing team — additional demand generation, content/brand, and marketing operations roles — prioritized against pipeline impact and budget.
• Introduce the systems, reporting, and rigor of a mature marketing organization, including clear goal-setting, attribution, and performance tracking.
• Build and execute multi-channel demand generation programs to drive qualified pipeline.
• Own Portside's brand positioning, voice, and visual identity across all channels.
• Manage the corporate website, ensuring messaging is current, compelling, and conversion-focused.
• Lead PR, analyst relations, and industry event strategy, including conference presence and sponsorships.
• Own marketing-sourced and marketing-influenced pipeline targets and report on performance to the executive team.
• Partner with Sales leadership to align marketing programs with revenue goals and target account strategies.
• Directly manage the BDR function responsible for outbound prospecting, inbound follow-up, and lead qualification, including building playbooks and conversion metrics.
• Partner with product marketing to ensure product positioning and messaging are clear, differentiated, and consistently applied across the company.
• Oversee the creation of sales enablement content, case studies, and campaign assets.
• Bring AI into how marketing operates — evaluate and adopt AI-powered tools across content, campaign, and marketing ops workflows to improve team efficiency, and help shape how Portside talks about AI as part of its product story.

Qualifications

• 8–10+ years of progressive marketing experience in B2B SaaS, including experience owning marketing broadly — brand, demand generation, and sales development — rather than a single specialty.
• Prior experience building or substantially scaling a marketing function at a small or early-stage company, with limited team and resources, and full autonomy over direction and priorities.
• Direct experience managing a BDR, SDR, or ISR team, including building playbooks and driving pipeline metrics.
• Comfortable moving fluidly between strategic planning and hands-on execution — writing copy, building a campaign, briefing a designer, running a webinar.
• Experience with CRM and marketing automation platforms (e.g., Salesforce, HubSpot, Marketo, Pardot).
• Excellent written and verbal communication skills, with the ability to represent marketing to the executive team and board.
• Bachelor's degree or equivalent work experience.
• Prior experience in aviation, aerospace, or a related industry (business aviation, airlines, or aircraft leasing & finance) is a plus, though not required for the right generalist operator.

What We Offer

• Competitive base salary
• Fully remote work
• Generous time off policy
• Health, dental, and vision insurance
• Opportunities for professional development and career advancement.
• Dynamic, collaborative, and fast-growing work environment.