VP, Sales

About Portside, Inc.

Portside is a leading provider of modern software solutions for the global aviation industry. As a fast-growing SaaS company, we operate across three key verticals: business aviation, regional commercial aviation, and aircraft leasing & finance. With nearly 300 team members spread across five continents, we support over 1,000 enterprise customers, helping them streamline and manage all aspects of their day-to-day operations.

Job Summary

Portside is seeking a Vice President of Sales to lead our global commercial organization and drive the growth of our aviation software platforms. This leader will be responsible for defining and executing the company’s revenue strategy, expanding our presence across business and government aviation, and building a scalable, high-performing sales organization.

The ideal candidate is both strategic and hands on, capable of setting vision while actively driving execution. This individual brings extensive experience in Aviation SaaS sales and a deep understanding of aviation operations, customer needs, and the broader industry landscape. This is an opportunity to make a significant impact at a fast-growing company transforming how aviation businesses operate.

This position requires up to 25% travel.

Key Responsibilities 

• Lead the development and execution of Portside’s global sales strategy, with a focus on accelerating ARR growth and expanding market presence.
• Build, manage, and mentor a high-performing sales team across regions and customer segments.
• Ensure consistent attainment of revenue targets through disciplined pipeline management, forecasting, and performance tracking.
• Collaborate closely with Marketing, Product, and Customer Success teams to deliver a cohesive go-to-market strategy and seamless customer experience.
• Establish and maintain strong relationships with key customers, partners, and aviation industry stakeholders.
• Define and refine sales processes, tools, and performance metrics to enable scalable and data-driven growth.
• Represent Portside at major aviation and technology industry events and conferences.
• Stay current on aviation technology trends, regulatory developments, and competitive dynamics across business and government aviation sectors.

Qualifications

• 7+ years of experience in B2B Aviation SaaS sales, including at least 5 years in sales leadership roles.
• Proven record of leading teams that consistently meet or exceed ARR and quota goals.
• Deep understanding of the business aviation ecosystem, including operators, management companies, OEMs, and government agencies.
• Demonstrated ability to sell complex technology solutions to aviation decision makers.
• Strong strategic thinking, analytical, and operational execution skills.
• Excellent communication, leadership, and presentation abilities, with confidence engaging at the executive level.
• Experience building and scaling global or multi-regional sales organizations is preferred.
• Bachelor’s degree required.

• 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.