Head of Marketing

Responsibilities

• Drive measurable revenue impact. Tie every meaningful marketing investment to a clear business hypothesis and a measured outcome across pipeline, bookings, expansion, pilot subscriptions, and retention. Build the baselines, attribution, and learning loops that guide budget decisions, and know when brand calls for longer-term indicators instead of last-touch precision.
• Build an always-on demand engine. Create sustained market presence through digital, content, field, community, advocacy, partnership, and performance programs, paired with major launches when warranted. Grow non-branded demand and pipeline quality for both a concentrated B2B buyer audience and a much larger pilot audience.
• Make product marketing a strategic advantage. Own segmentation, ideal customer profiles, competitive intelligence, win/loss, and voice of customer, along with positioning, launches, pricing and packaging research, and sales enablement. Turn complex capabilities into reasons to buy, expand, and stay, and shape how the business understands the roadmap.
• Grow revenue from existing customers. Build an installed-base growth strategy spanning cross-sell, upsell, account-based campaigns, education, advocacy, and retention. Partner with Account Management, Sales, Customer Experience, and Revenue Operations, treating expansion pipeline as a core Marketing outcome.
• Scale pilot subscription growth. Lead and support Pilot Growth, run day to day by our Head of Pilot Growth, across acquisition, conversion, lifecycle, retention, and win-back for Pilotbase Pilot and LogTen. Work with Product to move pilots from school-required usage to independently paid subscriptions.
• Build an unmistakable brand. Lead the expression of our brand architecture across Pilotbase, Flight Schedule Pro, Pilotbase Pilot, and LogTen while preserving each product’s earned equity. Bring strong aesthetic judgment and connect awareness and engagement to commercial goals.
• Architect an AI-native marketing function. Design how Marketing works with AI to scale market intelligence, accelerate testing, and personalize at scale, held to the same commercial standard as everything else. Faster content production is the floor; growth is the goal.
• Develop exceptional talent. Lead an accomplished multidisciplinary team: coach senior specialists and emerging leaders, clarify ownership, give direct feedback, and raise creative ambition without adding approval layers.

Requirements

• Growth-stage B2B SaaS marketing leadership
• Personally improving measurable pipeline or revenue contribution
• Product positioning and go-to-market leadership
• Demand generation and customer marketing or expansion
• Leading multidisciplinary teams and creative talent
• Financial and analytics fluency
• Subscription acquisition, activation, conversion and retention
• Persuasive, direct executive communication
• Specific examples of leading AI-led operational transformation in a marketing team, with measurable outcomes

Preferred

• - Private-equity-backed scaling
• - Multi-brand portfolios and brand architecture
• - B2B, B2B2C and B2C together
• - Product-led or freemium subscriptions
• - Category development
• - Professional communities; aviation, education or career development
• - Aviation background welcome, not required

Benefits

• - Full benefits package (Medical, Dental, Vision, Short-Term Disability, Life Insurance, 401(k) plan
• - Equity Appreciation Plan
• - Flexible Time Off policy
• - Seven (7) company-wide paid holidays + two (2) floating holidays
• - Two (2) wellness days
• - Employee Assistance Program
• - Professional Development Stipend
• - Home Office Stipend