About Portside

Portside is a leading provider of cloud-based software solutions for the global aviation industry. Our platform powers critical operations across business aviation, regional airlines, and aircraft leasing & finance, helping over 1,000 aviation organizations streamline operations, improve decision-making, and operate more efficiently.

Backed by leading technology investors Vista Equity Partners and Insight Partners, Portside is entering an exciting phase of growth. We are expanding our platform, investing in AI driven innovation, and building a global team focused on shaping the future of aviation technology.

Job Summary

Portside is seeking a high-performing Enterprise Sales Executive to drive new business across our suite of aviation SaaS solutions, including our Aircraft Owner Portal, Fleet & Crew Optimization tools, and Flight Management Systems.

This role is focused on selling into complex enterprise environments, specifically corporate flight departments. You will engage senior stakeholders, navigate multi-layered buying groups, and manage full-cycle sales across longer, consultative deal cycles. We’re looking for someone who is comfortable operating in high-value, multi-stakeholder deals and can position software as a strategic solution to operational and financial challenges.

Travel: up to 30%

Key Responsibilities 

• Identify and engage potential clients within the aviation industry, with a focus on corporate flight departments
• Present and demonstrate Portside’s SaaS solutions, highlighting features such as streamlined communication, operational efficiency, and financial management tools
• Navigate complex, multi-stakeholder sales cycles within corporate organizations
• Build and maintain strong client relationships to ensure customer satisfaction and repeat business
• Collaborate with marketing and product teams to develop targeted sales strategies and campaigns
• Stay up-to-date with industry trends and competitor offerings to effectively position Portside’s products

Qualifications

• 7+ years of experience in enterprise or complex B2B software sales
• Proven track record of closing high-value deals with multiple stakeholders
• Experience navigating long sales cycles (3–9+ months)
• Strong ability to engage and influence senior decision-makers
• Consultative selling approach with strong discovery and qualification skills
• Excellent communication, presentation, and negotiation abilities

• Experience selling into aviation, transportation, or highly regulated industries is a plus
• Familiarity with operational or financial SaaS solutions is nice to have

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.

Portside is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.